From 00d96b716323079b11b99003296700c27ab70d42 Mon Sep 17 00:00:00 2001
From: Hare <kei.hiracchi.0928@gmail.com>
Date: Fri, 30 Oct 2026 20:33:57 +0900
Subject: [PATCH] fix: scope Workdir removal to explicit requests

---
 crates/server-api/src/lib.rs                  |   2 +
 .../src/feature/builtin/manage_workdir.rs     |  97 ++-
 crates/workspace-server/src/server.rs         | 689 ++++++++++++++----
 .../src/server/tests/worker_drive_tests.rs    |   1 +
 .../src/server_workspace_config_tests.rs      |   1 +
 .../workspace-server/src/workdir_removal.rs   | 266 +++++--
 openapi/server-api.json                       |   7 +-
 .../src/lib/generated/companion-api.ts        |   2 +-
 .../src/lib/generated/repository-api.ts       |   2 +-
 .../src/lib/generated/runtime-api.ts          |   2 +-
 web/workspace/src/lib/generated/ticket-api.ts |   2 +-
 .../src/lib/generated/workdir-api.ts          |   4 +-
 .../src/lib/generated/worker-launch-api.ts    |   2 +-
 .../lib/workspace/settings/workdir-removal.ts |  38 +-
 .../[runtimeId]/workdirs/PageContent.svelte   |   5 +-
 web/workspace/tests/workdir-removal.test.ts   |  50 +-
 16 files changed, 916 insertions(+), 254 deletions(-)

diff --git a/crates/server-api/src/lib.rs b/crates/server-api/src/lib.rs
index 59b2d6b8f..17dba8b22 100644
--- a/crates/server-api/src/lib.rs
+++ b/crates/server-api/src/lib.rs
@@ -7064,6 +7064,8 @@ pub struct WorkingDirectoryCleanupTarget {
 #[cfg_attr(feature = "typescript", derive(ts_rs::TS))]
 #[serde(deny_unknown_fields)]
 pub struct WorkingDirectoryRemovalRequest {
+    /// Stable for an exact resend; a new explicit request uses a new identity.
+    pub operation_id: String,
     pub reason: String,
 }
 
diff --git a/crates/worker/src/feature/builtin/manage_workdir.rs b/crates/worker/src/feature/builtin/manage_workdir.rs
index 9158821de..a197867e2 100644
--- a/crates/worker/src/feature/builtin/manage_workdir.rs
+++ b/crates/worker/src/feature/builtin/manage_workdir.rs
@@ -778,7 +778,11 @@ impl WorkspaceHttpWorkdirBackend {
         )
     }
 
-    fn delete(&self, input: WorkdirDeleteInput) -> Result<ToolOutput, ToolError> {
+    fn delete(
+        &self,
+        input: WorkdirDeleteInput,
+        operation_id: String,
+    ) -> Result<ToolOutput, ToolError> {
         let workdir_id = validate_identity(
             &input.working_directory_id,
             DELETE_TOOL,
@@ -790,6 +794,7 @@ impl WorkspaceHttpWorkdirBackend {
             WorkspaceRequestMethod::Delete,
             format!("/api/w/{workspace_id}/working-directories/{workdir_path}"),
             serde_json::to_string(&WorkdirRemovalRequest {
+                operation_id,
                 reason: validate_delete_reason(&input.reason)?.to_string(),
             })
             .map_err(decode_error)?,
@@ -800,7 +805,7 @@ impl WorkspaceHttpWorkdirBackend {
                 response.disposition,
                 removal_guidance(response.failure_category.as_deref()),
                 if response.retryable {
-                    " After resolving the cause, repeat this WorkdirDelete with the same id and reason; current safety conditions will be rechecked."
+                    " After resolving the cause, a new explicit WorkdirDelete request will recheck current safety conditions. This failed request will not be automatically re-executed."
                 } else {
                     ""
                 }
@@ -954,9 +959,10 @@ impl Tool for WorkspaceHttpWorkdirTool {
                 self.backend.detach_managed(&input.alias, None).await
             }
 
-            WorkdirOperation::Delete => self
-                .backend
-                .delete(parse_input::<WorkdirDeleteInput>(input_json)?),
+            WorkdirOperation::Delete => self.backend.delete(
+                parse_input::<WorkdirDeleteInput>(input_json)?,
+                ctx.call_id.to_string(),
+            ),
         }
     }
 }
@@ -1018,8 +1024,14 @@ fn removal_guidance(category: Option<&str>) -> &'static str {
         Some("runtime_unavailable" | "provider_unavailable") => {
             "Restore the Runtime connection; the registry remains until deletion is confirmed."
         }
-        Some("provider_observation_unknown" | "provider_cleanup_outcome_unknown") => {
-            "Deletion is not confirmed. Re-observe with normal removal after restoring provider access; the registry is retained."
+        Some("provider_cleanup_outcome_unknown") => {
+            "Deletion outcome is unknown. Restore provider access and reconcile the existing request; do not submit a fresh deletion intent. Recovery only observes the target and never repeats deletion."
+        }
+        Some("provider_observation_unknown") => {
+            "The target could not be observed before deletion. Restore provider access before a new request."
+        }
+        Some("request_interrupted") => {
+            "The request was interrupted before execution. A new explicit request is required."
         }
         Some("unsupported_target") => {
             "Ask the owner for the provider's supported cleanup operation."
@@ -1337,8 +1349,44 @@ mod tests {
         })
     }
 
+    #[tokio::test]
+    async fn delete_call_identity_distinguishes_new_requests_from_exact_resends() {
+        let client = Arc::new(RecordingWorkspaceClient::new(
+            (0..3)
+                .map(|_| {
+                    response(json!({
+                        "working_directory_id": "wd-request",
+                        "disposition": "attention_required",
+                        "retryable": true,
+                        "failure_category": "resource_busy"
+                    }))
+                })
+                .collect(),
+        ));
+        let tool = WorkspaceHttpWorkdirTool {
+            backend: WorkspaceHttpWorkdirBackend::new(client.clone()),
+            operation: WorkdirOperation::Delete,
+        };
+        let input = r#"{"working_directory_id":"wd-request","reason":"remove unused Workdir"}"#;
+        for id in ["delete-1", "delete-1", "delete-2"] {
+            tool.execute(input, ToolExecutionContext::new(id, "batch", 0))
+                .await
+                .unwrap();
+        }
+        let bodies: Vec<serde_json::Value> = client
+            .requests()
+            .iter()
+            .map(|r| serde_json::from_str(r.body.as_deref().unwrap()).unwrap())
+            .collect();
+        assert_eq!(bodies[0], bodies[1]);
+        assert_eq!(bodies[0]["operation_id"], "delete-1");
+        assert_eq!(bodies[2]["operation_id"], "delete-2");
+        assert_eq!(bodies[0]["reason"], bodies[2]["reason"]);
+        assert!(delete_schema()["properties"].get("operation_id").is_none());
+    }
+
     #[test]
-    fn ordinary_workdir_delete_reports_safe_cause_and_exact_retry_guidance() {
+    fn ordinary_workdir_delete_reports_safe_cause_and_new_request_guidance() {
         let client = Arc::new(RecordingWorkspaceClient::new(vec![response(json!({
             "working_directory_id": "wd-retry",
             "disposition": "attention_required",
@@ -1347,10 +1395,13 @@ mod tests {
         }))]));
         let backend = WorkspaceHttpWorkdirBackend::new(client.clone());
         let output = backend
-            .delete(WorkdirDeleteInput {
-                working_directory_id: "wd-retry".into(),
-                reason: "remove unused Workdir".into(),
-            })
+            .delete(
+                WorkdirDeleteInput {
+                    working_directory_id: "wd-retry".into(),
+                    reason: "remove unused Workdir".into(),
+                },
+                "delete-call-1".to_string(),
+            )
             .unwrap();
         assert!(output.summary.contains("Confirm its owner"));
         assert!(
@@ -1358,7 +1409,11 @@ mod tests {
                 .summary
                 .contains("Do not recursively delete mounted data")
         );
-        assert!(output.summary.contains("same id and reason"));
+        assert!(
+            output
+                .summary
+                .contains("new explicit WorkdirDelete request")
+        );
         assert!(output.summary.len() <= 600);
         let content: serde_json::Value =
             serde_json::from_str(output.content.as_deref().unwrap()).unwrap();
@@ -1596,10 +1651,13 @@ mod tests {
             .unwrap();
         backend.detach("checkout").unwrap();
         backend
-            .delete(WorkdirDeleteInput {
-                working_directory_id: "wd-created".to_string(),
-                reason: "remove stale Workdir".to_string(),
-            })
+            .delete(
+                WorkdirDeleteInput {
+                    working_directory_id: "wd-created".to_string(),
+                    reason: "remove stale Workdir".to_string(),
+                },
+                "delete-call-1".to_string(),
+            )
             .unwrap();
 
         let requests = client.requests();
@@ -1637,7 +1695,10 @@ mod tests {
         assert_eq!(requests[4].method, WorkspaceRequestMethod::Delete);
         let body: serde_json::Value =
             serde_json::from_str(requests[4].body.as_deref().unwrap()).unwrap();
-        assert_eq!(body, json!({"reason": "remove stale Workdir"}));
+        assert_eq!(
+            body,
+            json!({"reason": "remove stale Workdir", "operation_id": "delete-call-1"})
+        );
     }
 
     #[tokio::test]
diff --git a/crates/workspace-server/src/server.rs b/crates/workspace-server/src/server.rs
index bca0a9580..dce299e60 100644
--- a/crates/workspace-server/src/server.rs
+++ b/crates/workspace-server/src/server.rs
@@ -26932,7 +26932,14 @@ async fn cleanup_runtime_working_directory(
         .host()?
         .run(move || {
             let registered_runtime =
-                registered_workdir_runtime_id(&api, &path.working_directory_id)?;
+                match registered_workdir_runtime_id(&api, &path.working_directory_id) {
+                    Ok(runtime) => runtime,
+                    Err(error) => api
+                        .config_store
+                        .completed_workdir_removal(api.workspace_id(), &path.working_directory_id)?
+                        .map(|removed| removed.runtime_id)
+                        .ok_or(error)?,
+                };
             if registered_runtime != path.runtime_id {
                 return Err(ApiError::from(Error::WorkspacePermissionDenied(
                     "Workdir does not belong to the requested Runtime".to_string(),
@@ -26943,6 +26950,7 @@ async fn cleanup_runtime_working_directory(
                 &path.working_directory_id,
                 &source_actor,
                 &request.reason,
+                &request.operation_id,
             )
             .map_err(ApiError::from)
         })
@@ -28230,6 +28238,7 @@ async fn cleanup_working_directory(
                 &path.working_directory_id,
                 &source_actor,
                 &request.reason,
+                &request.operation_id,
             )
             .map_err(ApiError::from)
         })
@@ -28969,8 +28978,14 @@ fn workdir_removal_failure_guidance(category: &str) -> &'static str {
         "runtime_unavailable" | "provider_unavailable" => {
             "Runtime is unavailable. Reconnect it, then retry deletion; the Workdir registry is retained."
         }
-        "provider_observation_unknown" | "provider_cleanup_outcome_unknown" => {
-            "Runtime has not confirmed deletion. Retry to re-observe the target; the Workdir registry is retained."
+        "provider_cleanup_outcome_unknown" => {
+            "Deletion outcome is unknown. Reconcile the existing request; recovery only observes and never repeats deletion."
+        }
+        "provider_observation_unknown" => {
+            "The target could not be observed before deletion. Restore provider access before a new request."
+        }
+        "request_interrupted" => {
+            "The request was interrupted before execution. A new explicit request is required."
         }
         "unsupported_target" => "This provider does not support Workdir deletion.",
         _ => {
@@ -29006,7 +29021,7 @@ fn current_workdir_removal_attempt_owner() -> Result<WorkdirRemovalAttemptOwner>
 
 fn workdir_removal_attempt_is_orphaned(operation: &WorkdirRemovalOperation) -> Result<bool> {
     let Some(owner) = operation.attempt_owner else {
-        return Ok(operation.attempt_id.is_none());
+        return Ok(true);
     };
     match observe_workdir_removal_owner(owner.process_id) {
         WorkdirRemovalOwnerObservation::Running {
@@ -29112,12 +29127,12 @@ fn execute_reserved_workdir_removal_with_provider(
     recovery: bool,
     provider: &dyn WorkdirRemovalRuntimeProvider,
 ) -> Result<WorkdirRemovalOperation> {
-    if operation.state == WorkdirRemovalOperationState::Completed
-        && operation.disposition == Some(WorkdirRemovalDisposition::Removed)
-    {
+    if operation.state != WorkdirRemovalOperationState::Pending {
         return Ok(operation);
     }
-    let operation = if recovery && operation.state == WorkdirRemovalOperationState::Pending {
+    let unstarted = operation.attempt_id.is_none();
+    let reconcile_only = recovery || !unstarted;
+    let operation = if reconcile_only {
         if !workdir_removal_attempt_is_orphaned(&operation)? {
             return Err(Error::WorkdirAttachmentConflict(format!(
                 "Workdir removal operation `{}` still has a live attempt owner",
@@ -29141,6 +29156,19 @@ fn execute_reserved_workdir_removal_with_provider(
             api.workdir_remove_attempt_owner,
         )?
     };
+    if operation.state != WorkdirRemovalOperationState::Pending {
+        return Ok(operation);
+    }
+    if reconcile_only {
+        if unstarted {
+            return api.config_store.fail_workdir_removal_operation(
+                &operation,
+                "request_interrupted",
+                true,
+            );
+        }
+        return reconcile_workdir_removal(api, &operation, provider);
+    }
     let guards = match api.config_store.workdir_removal_guards(&operation) {
         Ok(guards) => guards,
         Err(
@@ -29232,10 +29260,16 @@ fn execute_reserved_workdir_removal_with_provider(
     let deleted = match deleted {
         Ok(deleted) => deleted,
         Err(error) => {
-            let (category, retryable) = classify_workdir_provider_error(&error);
-            return api
-                .config_store
-                .fail_workdir_removal_operation(&operation, category, retryable);
+            if let RuntimeRegistryError::RuntimeOperationFailed { code, .. } = &error
+                && let Some(category) = workdir_cleanup_diagnostic_category(code)
+            {
+                return api.config_store.fail_workdir_removal_operation(
+                    &operation,
+                    category,
+                    category != "unsupported_target",
+                );
+            }
+            return api.config_store.record_workdir_removal_unknown(&operation);
         }
     };
     let deletion_confirmed = runtime_reports_workdir_not_found(&deleted)
@@ -29257,6 +29291,9 @@ fn execute_reserved_workdir_removal_with_provider(
             category,
             "Runtime did not confirm Workdir removal; registry retained"
         );
+        if deleted.state == InternalWorkerOperationState::Accepted {
+            return api.config_store.record_workdir_removal_unknown(&operation);
+        }
         return api.config_store.fail_workdir_removal_operation(
             &operation,
             category,
@@ -29280,42 +29317,71 @@ fn workdir_removal_execution_lock(
         .clone())
 }
 
+fn reserve_requested_workdir_removal(
+    api: &WorkspaceApi,
+    working_directory_id: &str,
+    source_actor: &str,
+    reason: &str,
+    request_id: &str,
+) -> Result<WorkdirRemovalOperation> {
+    let operation_id = crate::workdir_removal::workdir_removal_request_id(
+        api.workspace_id(),
+        source_actor,
+        request_id,
+    )?;
+    if let Some(existing) = api
+        .config_store
+        .get_workdir_removal_operation(api.workspace_id(), &operation_id)?
+    {
+        if existing.working_directory_id != working_directory_id
+            || existing.source_actor != source_actor
+            || existing.reason != reason
+        {
+            return Err(Error::WorkdirAttachmentConflict(
+                "Workdir removal request ID was reused with different input".into(),
+            ));
+        }
+        return Ok(existing);
+    }
+    let Some(workdir) = api
+        .config_store
+        .get_workdir_registry(api.workspace_id(), working_directory_id)?
+    else {
+        return api
+            .config_store
+            .completed_workdir_removal(api.workspace_id(), working_directory_id)?
+            .ok_or_else(|| {
+                Error::InvalidInput(format!("Unknown Workdir \x60{working_directory_id}\x60"))
+            });
+    };
+    let intent = workdir_removal_intent(&workdir, source_actor, reason, request_id)?;
+    api.config_store.reserve_workdir_removal_operation(&intent)
+}
+
 fn execute_workdir_removal(
     api: &WorkspaceApi,
     working_directory_id: &str,
     source_actor: &str,
     reason: &str,
+    request_id: &str,
 ) -> Result<WorkingDirectoryRemovalResponse> {
     let reason = reason.trim();
-    if reason.is_empty() || reason.len() > 500 {
+    if reason.is_empty() || reason.len() > 500 || reason.chars().any(char::is_control) {
         return Err(Error::InvalidInput(
-            "Workdir removal reason must be between 1 and 500 bytes".to_string(),
+            "Workdir removal reason must be between 1 and 500 bytes without controls".into(),
         ));
     }
     let lock = workdir_removal_execution_lock(api, working_directory_id)?;
     let _guard = lock
         .lock()
-        .map_err(|_| Error::Store("Workdir removal lock was poisoned".to_string()))?;
-
-    let operation = if let Some(existing) =
-        api.config_store.find_workdir_removal_operation_by_intent(
-            api.workspace_id(),
-            working_directory_id,
-            source_actor,
-            reason,
-        )? {
-        existing
-    } else {
-        let workdir = api
-            .config_store
-            .get_workdir_registry(api.workspace_id(), working_directory_id)?
-            .ok_or_else(|| {
-                Error::InvalidInput(format!("Unknown Workdir `{working_directory_id}`"))
-            })?;
-        let intent = workdir_removal_intent(&workdir, source_actor, reason)?;
-        api.config_store
-            .reserve_workdir_removal_operation(&intent)?
-    };
+        .map_err(|_| Error::Store("Workdir removal lock was poisoned".into()))?;
+    let operation = reserve_requested_workdir_removal(
+        api,
+        working_directory_id,
+        source_actor,
+        reason,
+        request_id,
+    )?;
     execute_reserved_workdir_removal(api, operation, false)
         .map(|operation| workdir_removal_response(&operation))
 }
@@ -29326,35 +29392,66 @@ fn execute_workdir_removal_for_workspace_deletion(
     parent_operation_id: &str,
 ) -> Result<WorkdirRemovalOperation> {
     let source_actor = format!("workspace-deletion:{parent_operation_id}");
-    let reason = "Workspace deletion";
+    let request_id = format!("{parent_operation_id}:{working_directory_id}");
     let lock = workdir_removal_execution_lock(api, working_directory_id)?;
     let _guard = lock
         .lock()
-        .map_err(|_| Error::Store("Workdir removal lock was poisoned".to_string()))?;
-    let operation = if let Some(existing) =
-        api.config_store.find_workdir_removal_operation_by_intent(
-            api.workspace_id(),
-            working_directory_id,
-            &source_actor,
-            reason,
-        )? {
-        existing
-    } else {
-        let workdir = api
-            .config_store
-            .get_workdir_registry(api.workspace_id(), working_directory_id)?
-            .ok_or_else(|| {
-                Error::InvalidInput(format!("Unknown Workdir `{working_directory_id}`"))
-            })?;
-        let intent = workdir_removal_intent(&workdir, &source_actor, reason)?;
-        api.config_store
-            .reserve_workdir_removal_operation(&intent)?
-    };
+        .map_err(|_| Error::Store("Workdir removal lock was poisoned".into()))?;
+    let operation = reserve_requested_workdir_removal(
+        api,
+        working_directory_id,
+        &source_actor,
+        "Workspace deletion",
+        &request_id,
+    )?;
     api.config_store
         .append_workspace_deletion_child_operation(parent_operation_id, &operation.operation_id)?;
     execute_reserved_workdir_removal(api, operation, false)
 }
 
+// Recovery may confirm an external effect, but never issues another deletion.
+fn reconcile_workdir_removal(
+    api: &WorkspaceApi,
+    operation: &WorkdirRemovalOperation,
+    provider: &dyn WorkdirRemovalRuntimeProvider,
+) -> Result<WorkdirRemovalOperation> {
+    let current = api
+        .config_store
+        .get_workdir_registry(&operation.workspace_id, &operation.working_directory_id)?;
+    if current.is_none() {
+        if api
+            .config_store
+            .completed_workdir_removal(&operation.workspace_id, &operation.working_directory_id)?
+            .is_some_and(|removed| {
+                removed.materialization_fingerprint == operation.materialization_fingerprint
+            })
+        {
+            return api.config_store.commit_workdir_removal_removed(operation);
+        }
+        return api.config_store.fail_workdir_removal_operation(
+            operation,
+            "authority_changed",
+            false,
+        );
+    }
+    if current.as_ref().is_some_and(|record| {
+        crate::workdir_removal::workdir_materialization_fingerprint(record)
+            != operation.materialization_fingerprint
+    }) {
+        return api.config_store.fail_workdir_removal_operation(
+            operation,
+            "authority_changed",
+            false,
+        );
+    }
+    match provider.observe_workdir(&operation.runtime_id, &operation.working_directory_id) {
+        Ok(observed) if runtime_reports_workdir_not_found(&observed) => {
+            api.config_store.commit_workdir_removal_removed(operation)
+        }
+        _ => api.config_store.record_workdir_removal_unknown(operation),
+    }
+}
+
 fn recover_workdir_removals(api: &WorkspaceApi) -> Result<()> {
     for operation in api
         .config_store
@@ -29798,6 +29895,7 @@ async fn execute_runtime_cleanup_with_context(
                             removal_candidate.workdir_id.as_str(),
                             &requester,
                             &format!("cleanup target {}", removal_candidate.target_id),
+                            &uuid::Uuid::now_v7().to_string(),
                         )
                     })
                     .await?;
@@ -33870,8 +33968,7 @@ fn finalize_spawn_compensation_after_worker_delete(
             api,
             workdir_id,
             "backend:worker_spawn_compensation",
-            "remove Workdir created by rejected Worker spawn",
-        ) {
+            "remove Workdir created by rejected Worker spawn", &uuid::Uuid::now_v7().to_string(),) {
             Ok(result) if result.disposition == WorkingDirectoryRemovalDisposition::Removed => {}
             Ok(result) => diagnostics.push(spawn_compensation_diagnostic(
                 "worker_spawn_compensation_workdir_cleanup_failed",
@@ -33907,8 +34004,7 @@ fn cleanup_spawn_created_workdirs(
             api,
             workdir_id,
             "backend:worker_spawn_compensation",
-            "remove Workdir created before rejected Worker spawn",
-        ) {
+            "remove Workdir created before rejected Worker spawn", &uuid::Uuid::now_v7().to_string(),) {
             Ok(result) if result.disposition == WorkingDirectoryRemovalDisposition::Removed => {}
             Ok(result) => diagnostics.push(spawn_compensation_diagnostic(
                 "worker_spawn_compensation_workdir_cleanup_failed",
@@ -60666,7 +60762,8 @@ mod tests {
         let app = build_router(api.clone());
 
         for (workdir_id, path, reason) in fixtures {
-            let body = serde_json::to_vec(&json!({ "reason": reason })).unwrap();
+            let body = serde_json::to_vec(&json!({ "reason": reason, "operation_id": workdir_id }))
+                .unwrap();
             let response = app
                 .clone()
                 .oneshot(runtime_source_request(
@@ -60700,11 +60797,14 @@ mod tests {
             );
             let operation = api
                 .config_store
-                .find_workdir_removal_operation_by_intent(
+                .get_workdir_removal_operation(
                     TEST_WORKSPACE_ID,
-                    workdir_id,
-                    "worker:runtime-source:worker-source",
-                    reason,
+                    &crate::workdir_removal::workdir_removal_request_id(
+                        TEST_WORKSPACE_ID,
+                        "worker:runtime-source:worker-source",
+                        workdir_id,
+                    )
+                    .unwrap(),
                 )
                 .unwrap()
                 .unwrap();
@@ -60712,6 +60812,29 @@ mod tests {
                 operation.source_actor,
                 "worker:runtime-source:worker-source"
             );
+            for request_id in [workdir_id.to_string(), format!("{workdir_id}-fresh")] {
+                let replay = app
+                    .clone()
+                    .oneshot(runtime_source_request(
+                        &identity,
+                        Some("worker-source"),
+                        "DELETE",
+                        &path,
+                        serde_json::to_vec(&json!({"reason": reason, "operation_id": request_id}))
+                            .unwrap(),
+                    ))
+                    .await
+                    .unwrap();
+                assert_eq!(replay.status(), StatusCode::OK);
+                let result: WorkingDirectoryRemovalResponse = serde_json::from_slice(
+                    &to_bytes(replay.into_body(), usize::MAX).await.unwrap(),
+                )
+                .unwrap();
+                assert_eq!(
+                    result.disposition,
+                    WorkingDirectoryRemovalDisposition::Removed
+                );
+            }
             assert_eq!(operation.state, WorkdirRemovalOperationState::Completed);
             assert_eq!(
                 operation.disposition,
@@ -60754,7 +60877,10 @@ mod tests {
                 None,
                 "DELETE",
                 &runtime_only_path,
-                serde_json::to_vec(&json!({ "reason": "runtime only" })).unwrap(),
+                serde_json::to_vec(
+                    &json!({ "reason": "runtime only", "operation_id": "denied-removal" }),
+                )
+                .unwrap(),
             ))
             .await
             .unwrap();
@@ -60773,7 +60899,10 @@ mod tests {
                         worker_runtime::auth::RUNTIME_REQUEST_SOURCE_PROOF_HEADER,
                         "not-a-valid-proof",
                     )
-                    .body(Body::from(json!({ "reason": "invalid proof" }).to_string()))
+                    .body(Body::from(
+                        json!({ "reason": "invalid proof", "operation_id": "denied-removal" })
+                            .to_string(),
+                    ))
                     .unwrap(),
             )
             .await
@@ -60789,7 +60918,8 @@ mod tests {
                     .uri(&unauthenticated_path)
                     .header(CONTENT_TYPE, "application/json")
                     .body(Body::from(
-                        json!({ "reason": "unauthenticated" }).to_string(),
+                        json!({ "reason": "unauthenticated", "operation_id": "denied-removal" })
+                            .to_string(),
                     ))
                     .unwrap(),
             )
@@ -60830,7 +60960,7 @@ mod tests {
             build_router(api.clone()),
             "DELETE",
             &path,
-            Some(json!({ "reason": reason })),
+            Some(json!({ "reason": reason, "operation_id": workdir_id })),
             &token,
             StatusCode::OK,
         )
@@ -60844,11 +60974,14 @@ mod tests {
         );
         let operation = api
             .config_store
-            .find_workdir_removal_operation_by_intent(
+            .get_workdir_removal_operation(
                 TEST_WORKSPACE_ID,
-                workdir_id,
-                &format!("account:account-{TEST_WORKSPACE_ID}"),
-                reason,
+                &crate::workdir_removal::workdir_removal_request_id(
+                    TEST_WORKSPACE_ID,
+                    &format!("account:account-{TEST_WORKSPACE_ID}"),
+                    workdir_id,
+                )
+                .unwrap(),
             )
             .unwrap()
             .unwrap();
@@ -61181,8 +61314,13 @@ mod tests {
             .unwrap();
         record.materialization_status = "pending".into();
         api.store.upsert_workdir_registry(&record).unwrap();
-        let intent =
-            workdir_removal_intent(&record, "account:owner", "remove docs checkout").unwrap();
+        let intent = workdir_removal_intent(
+            &record,
+            "account:owner",
+            "remove docs checkout",
+            "test-removal-request",
+        )
+        .unwrap();
         let pending = api
             .config_store
             .reserve_workdir_removal_operation(&intent)
@@ -61958,6 +62096,7 @@ mod tests {
             &record,
             "account:owner",
             &format!("remove {working_directory_id}"),
+            working_directory_id,
         )
         .unwrap();
         let operation = api
@@ -61967,6 +62106,212 @@ mod tests {
         (operation, summary)
     }
 
+    #[tokio::test]
+    async fn workdir_removal_failure_never_recovers_as_a_job_and_new_request_can_remove() {
+        let workspace = tempfile::tempdir().unwrap();
+        init_clean_git_workspace(workspace.path());
+        let api = test_api(workspace.path()).await;
+        let (operation, summary) = reserve_removal_fixture(&api, "terminal-busy");
+        let provider = FakeWorkdirRemovalProvider::new(
+            workdir_removal_result(
+                InternalWorkerOperationState::Accepted,
+                Some(summary.clone()),
+                Vec::new(),
+            ),
+            workdir_removal_result(
+                InternalWorkerOperationState::Rejected,
+                None,
+                vec![RuntimeDiagnostic {
+                    code: "working_directory_cleanup_resource_busy".into(),
+                    severity: HostDiagnosticSeverity::Warning,
+                    message: "busy".into(),
+                }],
+            ),
+        );
+        let failed =
+            execute_reserved_workdir_removal_with_provider(&api, operation, false, &provider)
+                .unwrap();
+        assert_eq!(failed.state, WorkdirRemovalOperationState::Failed);
+        for recovery in [false, true] {
+            assert_eq!(
+                execute_reserved_workdir_removal_with_provider(
+                    &api,
+                    failed.clone(),
+                    recovery,
+                    &provider
+                )
+                .unwrap(),
+                failed
+            );
+        }
+        assert_eq!(provider.cleanup_calls(), 1);
+        assert!(
+            api.config_store
+                .recoverable_workdir_removal_operations(api.workspace_id(), 100)
+                .unwrap()
+                .is_empty()
+        );
+        let new_request = reserve_requested_workdir_removal(
+            &api,
+            &failed.working_directory_id,
+            &failed.source_actor,
+            &failed.reason,
+            "new-explicit-request",
+        )
+        .unwrap();
+        assert_ne!(new_request.operation_id, failed.operation_id);
+        assert!(
+            reserve_requested_workdir_removal(
+                &api,
+                &failed.working_directory_id,
+                &failed.source_actor,
+                "changed reason",
+                "new-explicit-request"
+            )
+            .is_err()
+        );
+        assert!(
+            reserve_requested_workdir_removal(
+                &api,
+                "different-workdir",
+                &failed.source_actor,
+                &failed.reason,
+                "new-explicit-request"
+            )
+            .is_err()
+        );
+        let success = FakeWorkdirRemovalProvider::new(
+            workdir_removal_result(
+                InternalWorkerOperationState::Accepted,
+                Some(summary),
+                Vec::new(),
+            ),
+            confirmed_workdir_cleanup_result(),
+        );
+        let removed =
+            execute_reserved_workdir_removal_with_provider(&api, new_request, false, &success)
+                .unwrap();
+        assert_eq!(
+            removed.disposition,
+            Some(WorkdirRemovalDisposition::Removed)
+        );
+        let already_removed = execute_workdir_removal(
+            &api,
+            &failed.working_directory_id,
+            &failed.source_actor,
+            &failed.reason,
+            "another-explicit-request",
+        )
+        .unwrap();
+        assert_eq!(
+            already_removed.disposition,
+            WorkingDirectoryRemovalDisposition::Removed
+        );
+        assert_eq!(
+            execute_reserved_workdir_removal_with_provider(&api, failed.clone(), false, &success)
+                .unwrap(),
+            failed
+        );
+        assert_eq!(success.cleanup_calls(), 1);
+    }
+
+    #[tokio::test]
+    async fn workdir_removal_unknown_outcome_recovery_only_observes_and_confirms_absence() {
+        let workspace = tempfile::tempdir().unwrap();
+        init_clean_git_workspace(workspace.path());
+        let api = test_api(workspace.path()).await;
+        let (operation, summary) = reserve_removal_fixture(&api, "lost-delete-response");
+        let provider = FakeWorkdirRemovalProvider::new(
+            workdir_removal_result(
+                InternalWorkerOperationState::Accepted,
+                Some(summary.clone()),
+                Vec::new(),
+            ),
+            confirmed_workdir_cleanup_result(),
+        );
+        *provider.cleanup.lock().unwrap() =
+            Some(Err(RuntimeRegistryError::RuntimeOperationFailed {
+                runtime_id: "runtime-test".into(),
+                code: "transport_timeout".into(),
+                message: "response lost".into(),
+            }));
+        let unknown =
+            execute_reserved_workdir_removal_with_provider(&api, operation, false, &provider)
+                .unwrap();
+        assert_eq!(unknown.state, WorkdirRemovalOperationState::Pending);
+        assert_eq!(
+            unknown.failure_category.as_deref(),
+            Some("provider_cleanup_outcome_unknown")
+        );
+        assert!(!unknown.retryable);
+        assert!(
+            reserve_requested_workdir_removal(
+                &api,
+                &unknown.working_directory_id,
+                &unknown.source_actor,
+                &unknown.reason,
+                "do-not-fork-unknown"
+            )
+            .is_err()
+        );
+        *provider.observation.lock().unwrap() = Some(Ok(workdir_removal_result(
+            InternalWorkerOperationState::Accepted,
+            Some(summary),
+            Vec::new(),
+        )));
+        let still_unknown =
+            execute_reserved_workdir_removal_with_provider(&api, unknown, true, &provider).unwrap();
+        assert_eq!(still_unknown.state, WorkdirRemovalOperationState::Pending);
+        assert_eq!(provider.cleanup_calls(), 1);
+        *provider.observation.lock().unwrap() = Some(Ok(confirmed_workdir_cleanup_result()));
+        let removed =
+            execute_reserved_workdir_removal_with_provider(&api, still_unknown, true, &provider)
+                .unwrap();
+        assert_eq!(
+            removed.disposition,
+            Some(WorkdirRemovalDisposition::Removed)
+        );
+        assert_eq!(provider.cleanup_calls(), 1);
+        assert!(
+            api.store
+                .get_workdir_registry(api.workspace_id(), &removed.working_directory_id)
+                .unwrap()
+                .is_none()
+        );
+    }
+
+    #[tokio::test]
+    async fn workdir_removal_unstarted_request_recovery_does_not_start_deletion() {
+        let workspace = tempfile::tempdir().unwrap();
+        init_clean_git_workspace(workspace.path());
+        let api = test_api(workspace.path()).await;
+        let (operation, summary) = reserve_removal_fixture(&api, "unstarted-removal");
+        let provider = FakeWorkdirRemovalProvider::new(
+            workdir_removal_result(
+                InternalWorkerOperationState::Accepted,
+                Some(summary),
+                Vec::new(),
+            ),
+            confirmed_workdir_cleanup_result(),
+        );
+        let interrupted =
+            execute_reserved_workdir_removal_with_provider(&api, operation, true, &provider)
+                .unwrap();
+        assert_eq!(interrupted.state, WorkdirRemovalOperationState::Failed);
+        assert_eq!(
+            interrupted.failure_category.as_deref(),
+            Some("request_interrupted")
+        );
+        assert_eq!(provider.cleanup_calls(), 0);
+        assert!(provider.observation.lock().unwrap().is_some());
+        assert!(
+            api.store
+                .get_workdir_registry(api.workspace_id(), &interrupted.working_directory_id)
+                .unwrap()
+                .is_some()
+        );
+    }
+
     #[tokio::test]
     async fn injectable_provider_covers_cleanup_not_found_unknown_dirty_and_unsupported() {
         let workspace = tempfile::tempdir().unwrap();
@@ -62089,9 +62434,26 @@ mod tests {
             confirmed_workdir_cleanup_result(),
         );
         let dirty_attempt_id = dirty.attempt_id.clone();
+        let replay = execute_reserved_workdir_removal_with_provider(
+            &api,
+            dirty.clone(),
+            false,
+            &clean_retry_provider,
+        )
+        .unwrap();
+        assert_eq!(replay, dirty);
+        assert_eq!(clean_retry_provider.cleanup_calls(), 0);
+        let new_request = reserve_requested_workdir_removal(
+            &api,
+            &dirty.working_directory_id,
+            &dirty.source_actor,
+            &dirty.reason,
+            "new-clean-request",
+        )
+        .unwrap();
         let removed_after_retry = execute_reserved_workdir_removal_with_provider(
             &api,
-            dirty,
+            new_request,
             false,
             &clean_retry_provider,
         )
@@ -62215,7 +62577,8 @@ mod tests {
     }
 
     #[tokio::test]
-    async fn workdir_removal_retry_rechecks_pending_materialization_changes_and_attachments() {
+    async fn new_workdir_removal_request_rechecks_pending_materialization_changes_and_attachments()
+    {
         let workspace = tempfile::tempdir().unwrap();
         init_clean_git_workspace(workspace.path());
         let api = test_api(workspace.path()).await;
@@ -62263,8 +62626,16 @@ mod tests {
             ),
             confirmed_workdir_cleanup_result(),
         );
+        let request = reserve_requested_workdir_removal(
+            &api,
+            &failed.working_directory_id,
+            &failed.source_actor,
+            &failed.reason,
+            "dirty-request",
+        )
+        .unwrap();
         let dirty =
-            execute_reserved_workdir_removal_with_provider(&api, failed, false, &dirty_provider)
+            execute_reserved_workdir_removal_with_provider(&api, request, false, &dirty_provider)
                 .unwrap();
         assert_eq!(dirty.disposition, Some(WorkdirRemovalDisposition::Retained));
         assert!(dirty.retryable);
@@ -62280,9 +62651,21 @@ mod tests {
             ),
             confirmed_workdir_cleanup_result(),
         );
-        let occupied =
-            execute_reserved_workdir_removal_with_provider(&api, dirty, false, &occupied_provider)
-                .unwrap();
+        let request = reserve_requested_workdir_removal(
+            &api,
+            &dirty.working_directory_id,
+            &dirty.source_actor,
+            &dirty.reason,
+            "occupied-request",
+        )
+        .unwrap();
+        let occupied = execute_reserved_workdir_removal_with_provider(
+            &api,
+            request,
+            false,
+            &occupied_provider,
+        )
+        .unwrap();
         assert_eq!(
             occupied.failure_category.as_deref(),
             Some("blocked_by_live_authority")
@@ -62309,14 +62692,18 @@ mod tests {
             ),
             confirmed_workdir_cleanup_result(),
         );
-        let removed = execute_reserved_workdir_removal_with_provider(
+        let request = reserve_requested_workdir_removal(
             &api,
-            occupied.clone(),
-            false,
-            &retry_provider,
+            &occupied.working_directory_id,
+            &occupied.source_actor,
+            &occupied.reason,
+            "final-request",
         )
         .unwrap();
-        assert_eq!(removed.operation_id, occupied.operation_id);
+        let removed =
+            execute_reserved_workdir_removal_with_provider(&api, request, false, &retry_provider)
+                .unwrap();
+        assert_ne!(removed.operation_id, occupied.operation_id);
         assert_ne!(removed.attempt_id, occupied.attempt_id);
         assert_eq!(
             removed.disposition,
@@ -62415,7 +62802,15 @@ mod tests {
             let result =
                 execute_reserved_workdir_removal_with_provider(&api, operation, false, &provider)
                     .unwrap();
-            assert!(result.retryable);
+            assert_eq!(result.retryable, changed_identity);
+            assert_eq!(
+                result.state,
+                if changed_identity {
+                    WorkdirRemovalOperationState::Failed
+                } else {
+                    WorkdirRemovalOperationState::Pending
+                }
+            );
             assert_eq!(
                 result.failure_category.as_deref(),
                 Some(if changed_identity {
@@ -62449,7 +62844,7 @@ mod tests {
     }
 
     #[tokio::test]
-    async fn concurrent_orphan_recovery_runs_delayed_provider_cleanup_once() {
+    async fn concurrent_orphan_recovery_observes_once_without_reissuing_cleanup() {
         let workspace = tempfile::tempdir().unwrap();
         init_clean_git_workspace(workspace.path());
         let api = test_api(workspace.path()).await;
@@ -62504,7 +62899,9 @@ mod tests {
                 .iter()
                 .filter(|result| {
                     result.as_ref().is_ok_and(|operation| {
-                        operation.disposition == Some(WorkdirRemovalDisposition::Removed)
+                        operation.state == WorkdirRemovalOperationState::Pending
+                            && operation.failure_category.as_deref()
+                                == Some("provider_cleanup_outcome_unknown")
                     })
                 })
                 .count(),
@@ -62517,7 +62914,13 @@ mod tests {
                 .count(),
             1
         );
-        assert_eq!(provider.cleanup_calls(), 1);
+        assert_eq!(provider.cleanup_calls(), 0);
+        assert!(
+            api.store
+                .get_workdir_registry(TEST_WORKSPACE_ID, "orphan-race")
+                .unwrap()
+                .is_some()
+        );
     }
 
     #[test]
@@ -62546,65 +62949,64 @@ mod tests {
     }
 
     #[tokio::test]
-    async fn durable_workdir_removal_retries_provider_unavailable_without_deleting_registry() {
+    async fn failed_workdir_removal_replays_without_reexecution_and_new_request_is_distinct() {
         let workspace = tempfile::tempdir().unwrap();
         init_clean_git_workspace(workspace.path());
         let api = test_api(workspace.path()).await;
         seed_cleanup_workdir(&api, "missing-clean-workdir", "present", "clean");
-
-        let first = execute_workdir_removal(
-            &api,
-            "missing-clean-workdir",
-            "account:owner",
-            "remove stale clean Workdir",
-        )
-        .unwrap();
-        assert_eq!(
-            first.disposition,
-            WorkingDirectoryRemovalDisposition::AttentionRequired
-        );
-        assert!(first.retryable);
+        let request = |id| {
+            execute_workdir_removal(
+                &api,
+                "missing-clean-workdir",
+                "account:owner",
+                "remove stale clean Workdir",
+                id,
+            )
+            .unwrap()
+        };
+        let saved = |id| {
+            api.config_store
+                .get_workdir_removal_operation(
+                    api.workspace_id(),
+                    &crate::workdir_removal::workdir_removal_request_id(
+                        api.workspace_id(),
+                        "account:owner",
+                        id,
+                    )
+                    .unwrap(),
+                )
+                .unwrap()
+                .unwrap()
+        };
+        let first = request("request-1");
         assert_eq!(
             first.failure_category.as_deref(),
             Some("runtime_unavailable")
         );
+        let first_record = saved("request-1");
+        assert_eq!(request("request-1"), first);
+        assert_eq!(saved("request-1"), first_record);
+        recover_workdir_removals(&api).unwrap();
+        assert_eq!(saved("request-1"), first_record);
         assert!(
-            api.store
-                .get_workdir_registry(&api.config.workspace_id, "missing-clean-workdir")
+            api.config_store
+                .recoverable_workdir_removal_operations(api.workspace_id(), 100)
                 .unwrap()
-                .is_some()
+                .is_empty()
         );
-
-        let first_attempt_id = api
-            .config_store
-            .find_workdir_removal_operation_by_intent(
-                &api.config.workspace_id,
+        assert_eq!(request("request-2"), first);
+        assert_ne!(saved("request-2").operation_id, first_record.operation_id);
+        assert_ne!(saved("request-2").attempt_id, first_record.attempt_id);
+        assert!(
+            execute_workdir_removal(
+                &api,
                 "missing-clean-workdir",
                 "account:owner",
-                "remove stale clean Workdir",
+                "different reason",
+                "request-1"
             )
-            .unwrap()
-            .unwrap()
-            .attempt_id;
-        let retry = execute_workdir_removal(
-            &api,
-            "missing-clean-workdir",
-            "account:owner",
-            "remove stale clean Workdir",
-        )
-        .unwrap();
-        assert_eq!(retry, first);
-        let operation = api
-            .config_store
-            .find_workdir_removal_operation_by_intent(
-                &api.config.workspace_id,
-                "missing-clean-workdir",
-                "account:owner",
-                "remove stale clean Workdir",
-            )
-            .unwrap()
-            .unwrap();
-        assert_ne!(operation.attempt_id, first_attempt_id);
+            .is_err()
+        );
     }
 
     #[tokio::test]
@@ -62621,6 +63023,7 @@ mod tests {
             "occupied-workdir",
             "account:owner",
             "remove occupied Workdir",
+            &uuid::Uuid::now_v7().to_string(),
         )
         .unwrap();
         assert_eq!(
@@ -62654,6 +63057,7 @@ mod tests {
             &record,
             "account:owner",
             "do not steal a live provider call",
+            "test-removal-request",
         )
         .unwrap();
         let reserved = api
@@ -62696,8 +63100,13 @@ mod tests {
             .get_workdir_registry(&api.config.workspace_id, "recovery-workdir")
             .unwrap()
             .unwrap();
-        let intent =
-            workdir_removal_intent(&record, "account:owner", "recover provider cleanup").unwrap();
+        let intent = workdir_removal_intent(
+            &record,
+            "account:owner",
+            "recover provider cleanup",
+            "test-removal-request",
+        )
+        .unwrap();
         let reserved = api
             .config_store
             .reserve_workdir_removal_operation(&intent)
@@ -62723,12 +63132,12 @@ mod tests {
             .get_workdir_removal_operation(&api.config.workspace_id, &intent.operation_id)
             .unwrap()
             .unwrap();
-        assert_eq!(operation.state, WorkdirRemovalOperationState::Failed);
+        assert_eq!(operation.state, WorkdirRemovalOperationState::Pending);
         assert_ne!(operation.attempt_id, interrupted_attempt.attempt_id);
-        assert!(operation.retryable);
+        assert!(!operation.retryable);
         assert_eq!(
             operation.failure_category.as_deref(),
-            Some("runtime_unavailable")
+            Some("provider_cleanup_outcome_unknown")
         );
         assert!(
             api.store
diff --git a/crates/workspace-server/src/server/tests/worker_drive_tests.rs b/crates/workspace-server/src/server/tests/worker_drive_tests.rs
index f92b6d172..c0001b321 100644
--- a/crates/workspace-server/src/server/tests/worker_drive_tests.rs
+++ b/crates/workspace-server/src/server/tests/worker_drive_tests.rs
@@ -652,6 +652,7 @@ async fn source_workdir_removal_keeps_published_drive_bytes_and_receipt() {
             &removal_id,
             "account:drive-test",
             "source no longer needed",
+            "drive-source-removal",
         )
     })
     .await
diff --git a/crates/workspace-server/src/server_workspace_config_tests.rs b/crates/workspace-server/src/server_workspace_config_tests.rs
index 1c932be1a..9bbc39641 100644
--- a/crates/workspace-server/src/server_workspace_config_tests.rs
+++ b/crates/workspace-server/src/server_workspace_config_tests.rs
@@ -819,6 +819,7 @@ mod workspace_config_integration {
                 },
                 "owner".into(),
                 WorkingDirectoryRemovalRequest {
+                    operation_id: "unsupported-logical-cleanup".into(),
                     reason: "unsupported logical cleanup".into()
                 }
             )
diff --git a/crates/workspace-server/src/workdir_removal.rs b/crates/workspace-server/src/workdir_removal.rs
index 46378b3a7..c7f3b62e4 100644
--- a/crates/workspace-server/src/workdir_removal.rs
+++ b/crates/workspace-server/src/workdir_removal.rs
@@ -1,24 +1,15 @@
-//! Persists durable deletion intent and attempts for Repository-backed Workdirs.
+//! Records one Repository-backed Workdir removal request and its result.
 //!
-//! Deletion intent fixes Workspace, Workdir, owning Runtime, Repository/materialization, actor,
-//! and reason. Endpoints, host paths, and provider handles do not grant caller deletion authority.
+//! Caller-generated request identities distinguish an exact resend from a new explicit request;
+//! reason text is audit input, never a replay key. Failed and completed records are terminal,
+//! including legacy failed records marked retryable. Retryability only advises a new explicit
+//! request after resolving its cause; it is not continuing authority to delete.
+//!
+//! Only one unresolved request per Workdir is allowed. Attempts are claimed transactionally and
+//! fenced by process/start marker and attempt identity. Recovery observes uncertain external
+//! effects but never reissues deletion. Confirmed absence and the matching materialization permit
+//! registry removal and the saved result to commit together. Unconfirmed effects remain pending.
 //! External Workdirs follow grant revocation, not this operation.
-//!
-//! Only one pending operation per Workdir is allowed; attempts are claimed transactionally.
-//! Process IDs and startup markers are retained. Recovery reclaims the exact owner/attempt by
-//! compare-and-set only after confirming the previous owner is gone; live or unobservable owners
-//! are not displaced. In-process locks alone are insufficient.
-//!
-//! Server execution revalidates stored materialization and current attachments, reservations,
-//! assignments, retention, and creation operations, then observes occupancy and cleanliness via
-//! Runtime. Dirty resources remain; unknown observations or provider failures retain the registry
-//! and record attention/retryability. Only confirmed deletion or exact working_directory_not_found
-//! is deletion evidence; registry removal and completed/removed commit in the same transaction.
-//!
-//! Normal deletion, Workspace deletion, cleanup, and startup recovery use the same reserved Server
-//! operation execution. Failed DB commits after provider deletion are reobserved through that
-//! operation. Recovery relies on provider identity and results, not an exactly-once guarantee
-//! across all interruption points.
 
 use chrono::Utc;
 use rusqlite::{Connection, OptionalExtension, TransactionBehavior, params};
@@ -118,10 +109,22 @@ pub fn workdir_materialization_fingerprint(record: &WorkdirRegistryRecord) -> St
     hex_sha256(&bytes)
 }
 
+pub fn workdir_removal_request_id(
+    workspace_id: &str,
+    source_actor: &str,
+    request_id: &str,
+) -> Result<String> {
+    validate_bounded("operation id", request_id, 256)?;
+    let bytes = serde_json::to_vec(&(workspace_id, source_actor, request_id))
+        .map_err(|error| Error::Store(error.to_string()))?;
+    Ok(format!("wdr_{}", &hex_sha256(&bytes)[..32]))
+}
+
 pub fn workdir_removal_intent(
     record: &WorkdirRegistryRecord,
     source_actor: &str,
     reason: &str,
+    request_id: &str,
 ) -> Result<WorkdirRemovalIntent> {
     validate_bounded("source actor", source_actor, MAX_ACTOR_BYTES)?;
     validate_bounded("reason", reason, MAX_REASON_BYTES)?;
@@ -146,7 +149,7 @@ pub fn workdir_removal_intent(
         ));
     };
     Ok(WorkdirRemovalIntent {
-        operation_id: format!("wdr_{}", &request_fingerprint[..32]),
+        operation_id: workdir_removal_request_id(&record.workspace_id, source_actor, request_id)?,
         request_fingerprint,
         workspace_id: record.workspace_id.clone(),
         working_directory_id: record.workdir_id.clone(),
@@ -285,17 +288,10 @@ impl SqliteWorkspaceStore {
             let tx = conn.transaction_with_behavior(TransactionBehavior::Immediate)?;
             let operation =
                 require_operation(&tx, workspace_id, operation_id, request_fingerprint)?;
-            if operation.state == WorkdirRemovalOperationState::Completed
-                && operation.disposition == Some(WorkdirRemovalDisposition::Removed)
-            {
+            if operation.state != WorkdirRemovalOperationState::Pending {
                 tx.commit()?;
                 return Ok(operation);
             }
-            if operation.state == WorkdirRemovalOperationState::Failed && !operation.retryable {
-                return Err(Error::InvalidInput(format!(
-                    "Workdir removal operation `{operation_id}` is not retryable"
-                )));
-            }
             if let Some((expected_owner, expected_attempt_id)) = recovery_expected {
                 if operation.state != WorkdirRemovalOperationState::Pending
                     || operation.attempt_owner != expected_owner
@@ -473,7 +469,7 @@ impl SqliteWorkspaceStore {
                 &operation.operation_id,
                 &operation.request_fingerprint,
             )?;
-            if current.state == WorkdirRemovalOperationState::Completed {
+            if current.state != WorkdirRemovalOperationState::Pending {
                 tx.commit()?;
                 return Ok(current);
             }
@@ -502,6 +498,39 @@ impl SqliteWorkspaceStore {
         })
     }
 
+    /// Keep an uncertain external outcome for observation, not automatic re-execution.
+    pub fn record_workdir_removal_unknown(
+        &self,
+        operation: &WorkdirRemovalOperation,
+    ) -> Result<WorkdirRemovalOperation> {
+        self.with_conn_mut(|conn| {
+            let tx = conn.transaction_with_behavior(TransactionBehavior::Immediate)?;
+            let current = require_operation(
+                &tx,
+                &operation.workspace_id,
+                &operation.operation_id,
+                &operation.request_fingerprint,
+            )?;
+            if current.state != WorkdirRemovalOperationState::Pending {
+                tx.commit()?;
+                return Ok(current);
+            }
+            require_matching_attempt(operation, &current)?;
+            tx.execute(
+                "UPDATE workdir_removal_operations SET retryable=0, disposition='attention_required', failure_category='provider_cleanup_outcome_unknown', attempt_owner_pid=NULL, attempt_owner_start_marker=NULL, updated_at=?1 WHERE workspace_id=?2 AND operation_id=?3",
+                params![Utc::now().to_rfc3339(), operation.workspace_id, operation.operation_id],
+            )?;
+            let updated = require_operation(
+                &tx,
+                &operation.workspace_id,
+                &operation.operation_id,
+                &operation.request_fingerprint,
+            )?;
+            tx.commit()?;
+            Ok(updated)
+        })
+    }
+
     pub fn commit_workdir_removal_removed(
         &self,
         operation: &WorkdirRemovalOperation,
@@ -531,7 +560,7 @@ impl SqliteWorkspaceStore {
                 &operation.operation_id,
                 &operation.request_fingerprint,
             )?;
-            if current.state == WorkdirRemovalOperationState::Completed {
+            if current.state != WorkdirRemovalOperationState::Pending {
                 tx.commit()?;
                 return Ok(current);
             }
@@ -541,24 +570,29 @@ impl SqliteWorkspaceStore {
                     &tx,
                     &operation.workspace_id,
                     &operation.working_directory_id,
-                )?
-                .ok_or_else(|| Error::RegistryInconsistency(
-                    "Workdir registry row disappeared before durable removal commit".to_string(),
-                ))?;
-                require_operation_materialization(operation, &registry)?;
-                require_no_removal_blockers(
-                    &tx,
-                    &operation.workspace_id,
-                    &operation.working_directory_id,
                 )?;
-                let deleted = tx.execute(
-                    "DELETE FROM workdir_registry WHERE workspace_id=?1 AND workdir_id=?2",
-                    params![operation.workspace_id, operation.working_directory_id],
-                )?;
-                if deleted != 1 {
-                    return Err(Error::RegistryInconsistency(
-                        "Workdir registry deletion did not remove exactly one row".to_string(),
-                    ));
+                if let Some(registry) = registry {
+                    require_operation_materialization(operation, &registry)?;
+                    require_no_removal_blockers(
+                        &tx,
+                        &operation.workspace_id,
+                        &operation.working_directory_id,
+                    )?;
+                    tx.execute(
+                        "DELETE FROM workdir_registry WHERE workspace_id=?1 AND workdir_id=?2",
+                        params![operation.workspace_id, operation.working_directory_id],
+                    )?;
+                } else {
+                    let removed: bool = tx.query_row(
+                        "SELECT EXISTS(SELECT 1 FROM workdir_removal_operations WHERE workspace_id=?1 AND workdir_id=?2 AND materialization_fingerprint=?3 AND state='completed' AND disposition='removed')",
+                        params![operation.workspace_id, operation.working_directory_id, operation.materialization_fingerprint],
+                        |row| row.get(0),
+                    )?;
+                    if !removed {
+                        return Err(Error::RegistryInconsistency(
+                            "Workdir registry disappeared without confirmed removal".to_string(),
+                        ));
+                    }
                 }
             }
             let now = Utc::now().to_rfc3339();
@@ -585,20 +619,18 @@ impl SqliteWorkspaceStore {
         })
     }
 
-    pub fn find_workdir_removal_operation_by_intent(
+    pub fn completed_workdir_removal(
         &self,
         workspace_id: &str,
         working_directory_id: &str,
-        source_actor: &str,
-        reason: &str,
     ) -> Result<Option<WorkdirRemovalOperation>> {
         self.with_conn(|conn| {
             conn.query_row(
                 &format!(
-                    "{} WHERE workspace_id=?1 AND workdir_id=?2 AND source_actor=?3 AND reason=?4 ORDER BY created_at DESC, operation_id DESC LIMIT 1",
+                    "{} WHERE workspace_id=?1 AND workdir_id=?2 AND state='completed' AND disposition='removed' ORDER BY completed_at DESC, operation_id DESC LIMIT 1",
                     operation_select_sql()
                 ),
-                params![workspace_id, working_directory_id, source_actor, reason],
+                params![workspace_id, working_directory_id],
                 read_operation,
             )
             .optional()
@@ -614,7 +646,7 @@ impl SqliteWorkspaceStore {
         self.with_conn(|conn| {
             let mut statement = conn.prepare(
                 &format!(
-                    "{} WHERE workspace_id=?1 AND (state='pending' OR (state='failed' AND retryable=1)) ORDER BY updated_at ASC, operation_id ASC LIMIT ?2",
+                    "{} WHERE workspace_id=?1 AND state='pending' ORDER BY updated_at ASC, operation_id ASC LIMIT ?2",
                     operation_select_sql()
                 ),
             )?;
@@ -1007,8 +1039,13 @@ mod tests {
     #[tokio::test]
     async fn exact_replay_reuses_operation_and_conflicting_intent_fails() {
         let (store, workdir) = seeded_store().await;
-        let intent =
-            workdir_removal_intent(&workdir, "worker:W-1", "remove stale Workdir").unwrap();
+        let intent = workdir_removal_intent(
+            &workdir,
+            "worker:W-1",
+            "remove stale Workdir",
+            "test-removal-request",
+        )
+        .unwrap();
         let first = store.reserve_workdir_removal_operation(&intent).unwrap();
         let replay = store.reserve_workdir_removal_operation(&intent).unwrap();
         assert_eq!(replay, first);
@@ -1023,10 +1060,15 @@ mod tests {
     }
 
     #[tokio::test]
-    async fn failed_attempt_is_retryable_and_completed_retry_replays() {
+    async fn failed_request_is_terminal_and_new_request_has_independent_result() {
         let (store, workdir) = seeded_store().await;
-        let intent =
-            workdir_removal_intent(&workdir, "workspace-api", "remove clean Workdir").unwrap();
+        let intent = workdir_removal_intent(
+            &workdir,
+            "workspace-api",
+            "remove clean Workdir",
+            "test-removal-request",
+        )
+        .unwrap();
         let reserved = store.reserve_workdir_removal_operation(&intent).unwrap();
         let first = store
             .begin_workdir_removal_attempt(
@@ -1049,7 +1091,32 @@ mod tests {
                 attempt_owner(),
             )
             .unwrap();
-        assert_ne!(retry.attempt_id, first.attempt_id);
+        assert_eq!(retry, failed);
+        assert!(
+            store
+                .recoverable_workdir_removal_operations("workspace-a", 100)
+                .unwrap()
+                .is_empty()
+        );
+        let next_intent = workdir_removal_intent(
+            &workdir,
+            "workspace-api",
+            "remove clean Workdir",
+            "new-request",
+        )
+        .unwrap();
+        let next = store
+            .reserve_workdir_removal_operation(&next_intent)
+            .unwrap();
+        let retry = store
+            .begin_workdir_removal_attempt(
+                &next.workspace_id,
+                &next.operation_id,
+                &next.request_fingerprint,
+                attempt_owner(),
+            )
+            .unwrap();
+        assert_ne!(retry.operation_id, failed.operation_id);
         let completed = store.commit_workdir_removal_removed(&retry).unwrap();
         assert_eq!(
             completed.disposition,
@@ -1075,7 +1142,13 @@ mod tests {
     #[tokio::test]
     async fn recovery_and_completion_are_fenced_by_attempt_identity() {
         let (store, workdir) = seeded_store().await;
-        let intent = workdir_removal_intent(&workdir, "workspace-api", "remove Workdir").unwrap();
+        let intent = workdir_removal_intent(
+            &workdir,
+            "workspace-api",
+            "remove Workdir",
+            "test-removal-request",
+        )
+        .unwrap();
         let reserved = store.reserve_workdir_removal_operation(&intent).unwrap();
         let first = store
             .begin_workdir_removal_attempt(
@@ -1130,8 +1203,13 @@ mod tests {
         use std::sync::{Arc, Barrier};
 
         let (store, workdir) = seeded_store().await;
-        let intent =
-            workdir_removal_intent(&workdir, "workspace-api", "remove clean Workdir").unwrap();
+        let intent = workdir_removal_intent(
+            &workdir,
+            "workspace-api",
+            "remove clean Workdir",
+            "test-removal-request",
+        )
+        .unwrap();
         let operation = store.reserve_workdir_removal_operation(&intent).unwrap();
         let barrier = Arc::new(Barrier::new(3));
         let provider_calls = Arc::new(AtomicUsize::new(0));
@@ -1218,8 +1296,13 @@ mod tests {
                 "2",
             )
             .unwrap();
-        let intent =
-            workdir_removal_intent(&workdir, "workspace-api", "remove clean Workdir").unwrap();
+        let intent = workdir_removal_intent(
+            &workdir,
+            "workspace-api",
+            "remove clean Workdir",
+            "test-removal-request",
+        )
+        .unwrap();
         store.reserve_workdir_removal_operation(&intent).unwrap();
 
         let error = store
@@ -1236,8 +1319,13 @@ mod tests {
     #[tokio::test]
     async fn pending_removal_fences_new_attachment_and_retry_rereads_live_reservation() {
         let (store, workdir) = seeded_store().await;
-        let intent =
-            workdir_removal_intent(&workdir, "workspace-api", "remove clean Workdir").unwrap();
+        let intent = workdir_removal_intent(
+            &workdir,
+            "workspace-api",
+            "remove clean Workdir",
+            "test-removal-request",
+        )
+        .unwrap();
         let pending = store.reserve_workdir_removal_operation(&intent).unwrap();
 
         let error = store
@@ -1251,11 +1339,22 @@ mod tests {
         store
             .reserve_worker_workdir_attachment("workspace-a", "workdir-a", "reservation-b", "3")
             .unwrap();
+        let next_intent = workdir_removal_intent(
+            &workdir,
+            "workspace-api",
+            "remove clean Workdir",
+            "new-request",
+        )
+        .unwrap();
+        let next = store
+            .reserve_workdir_removal_operation(&next_intent)
+            .unwrap();
+        assert_ne!(next.operation_id, failed.operation_id);
         let retry = store
             .begin_workdir_removal_attempt(
-                &failed.workspace_id,
-                &failed.operation_id,
-                &failed.request_fingerprint,
+                &next.workspace_id,
+                &next.operation_id,
+                &next.request_fingerprint,
                 attempt_owner(),
             )
             .unwrap();
@@ -1324,7 +1423,13 @@ mod tests {
                     Ok(())
                 })
                 .unwrap();
-        let intent = workdir_removal_intent(&workdir, "workspace-api", "remove Workdir").unwrap();
+        let intent = workdir_removal_intent(
+            &workdir,
+            "workspace-api",
+            "remove Workdir",
+            "test-removal-request",
+        )
+        .unwrap();
         let operation = store.reserve_workdir_removal_operation(&intent).unwrap();
         let categories = |guards: Vec<WorkdirRemovalGuard>| {
             guards
@@ -1447,8 +1552,13 @@ mod tests {
     #[tokio::test]
     async fn retained_completion_keeps_registry_and_is_auditable() {
         let (store, workdir) = seeded_store().await;
-        let intent =
-            workdir_removal_intent(&workdir, "workspace-api", "inspect dirty Workdir").unwrap();
+        let intent = workdir_removal_intent(
+            &workdir,
+            "workspace-api",
+            "inspect dirty Workdir",
+            "test-removal-request",
+        )
+        .unwrap();
         let operation = store.reserve_workdir_removal_operation(&intent).unwrap();
         let retained = store
             .complete_workdir_removal_retained(
@@ -1477,10 +1587,12 @@ mod tests {
                 attempt_owner(),
             )
             .unwrap();
-        assert_eq!(retry.state, WorkdirRemovalOperationState::Pending);
-        assert!(retry.attempt_id.is_some());
-        assert_eq!(retry.disposition, None);
-        assert_eq!(retry.failure_category, None);
-        assert!(retry.retryable);
+        assert_eq!(retry, retained);
+        assert!(
+            store
+                .recoverable_workdir_removal_operations("workspace-a", 100)
+                .unwrap()
+                .is_empty()
+        );
     }
 }
diff --git a/openapi/server-api.json b/openapi/server-api.json
index ac5c7b8ea..fb1437af1 100644
--- a/openapi/server-api.json
+++ b/openapi/server-api.json
@@ -16290,11 +16290,16 @@
       "WorkingDirectoryRemovalRequest": {
         "additionalProperties": false,
         "properties": {
+          "operation_id": {
+            "description": "Stable for an exact resend; a new explicit request uses a new identity.",
+            "type": "string"
+          },
           "reason": {
             "type": "string"
           }
         },
         "required": [
+          "operation_id",
           "reason"
         ],
         "type": "object"
@@ -18302,7 +18307,7 @@
   "info": {
     "title": "Yoi Server API",
     "version": "0.1.0",
-    "x-yoi-source-digest": "sha256:7e640cff6bdcf6dc298cfca695c5cb71a520288b20f4f29ec8df8138724b97c4"
+    "x-yoi-source-digest": "sha256:3436eada52ceea48f4c50f40195cba02bec37fbbff4ea8f5a332133e6fcde962"
   },
   "openapi": "3.1.0",
   "paths": {
diff --git a/web/workspace/src/lib/generated/companion-api.ts b/web/workspace/src/lib/generated/companion-api.ts
index c886812bb..e9c1be932 100644
--- a/web/workspace/src/lib/generated/companion-api.ts
+++ b/web/workspace/src/lib/generated/companion-api.ts
@@ -1,6 +1,6 @@
 // @generated by yoi-companion-openapi-typescript@1. Do not edit.
 // Input: openapi/server-api.json
-// Input contract: 0.1.0 (sha256:7e640cff6bdcf6dc298cfca695c5cb71a520288b20f4f29ec8df8138724b97c4)
+// Input contract: 0.1.0 (sha256:3436eada52ceea48f4c50f40195cba02bec37fbbff4ea8f5a332133e6fcde962)
 // Options: companion-operation-schema-closure,openapi-3.1,strict-integer-ranges,sorted-output
 // Output: web/workspace/src/lib/generated/companion-api.ts
 // Regenerate/check: cargo run -q -p server-api --example generate_companion_api_types -- --check
diff --git a/web/workspace/src/lib/generated/repository-api.ts b/web/workspace/src/lib/generated/repository-api.ts
index 8cafc53b8..c97c6e513 100644
--- a/web/workspace/src/lib/generated/repository-api.ts
+++ b/web/workspace/src/lib/generated/repository-api.ts
@@ -1,6 +1,6 @@
 // @generated by yoi-repository-openapi-typescript@1. Do not edit.
 // Input: openapi/server-api.json
-// Input contract: 0.1.0 (sha256:7e640cff6bdcf6dc298cfca695c5cb71a520288b20f4f29ec8df8138724b97c4)
+// Input contract: 0.1.0 (sha256:3436eada52ceea48f4c50f40195cba02bec37fbbff4ea8f5a332133e6fcde962)
 // Options: repository-operation-schema-closure,openapi-3.1,format:uint64=safe-number,strict-safe-integers,sorted-output
 // Output: web/workspace/src/lib/generated/repository-api.ts
 // Regenerate/check: cargo run -q -p server-api --example generate_repository_openapi_types -- --check
diff --git a/web/workspace/src/lib/generated/runtime-api.ts b/web/workspace/src/lib/generated/runtime-api.ts
index c12b6c31e..9a9560295 100644
--- a/web/workspace/src/lib/generated/runtime-api.ts
+++ b/web/workspace/src/lib/generated/runtime-api.ts
@@ -1,6 +1,6 @@
 // @generated by yoi-runtime-openapi-typescript@1. Do not edit.
 // Input: openapi/server-api.json
-// Input contract: 0.1.0 (sha256:7e640cff6bdcf6dc298cfca695c5cb71a520288b20f4f29ec8df8138724b97c4)
+// Input contract: 0.1.0 (sha256:3436eada52ceea48f4c50f40195cba02bec37fbbff4ea8f5a332133e6fcde962)
 // Options: runtime-operation-schema-closure,openapi-3.1,strict-integer-ranges,sorted-output
 // Output: web/workspace/src/lib/generated/runtime-api.ts
 // Regenerate/check: cargo run -q -p server-api --example generate_runtime_api_types -- --check
diff --git a/web/workspace/src/lib/generated/ticket-api.ts b/web/workspace/src/lib/generated/ticket-api.ts
index b653b6d8a..74e10e252 100644
--- a/web/workspace/src/lib/generated/ticket-api.ts
+++ b/web/workspace/src/lib/generated/ticket-api.ts
@@ -1,6 +1,6 @@
 // @generated by yoi-ticket-browser-openapi-typescript@1. Do not edit.
 // Input: openapi/server-api.json
-// Input contract: 0.1.0 (sha256:7e640cff6bdcf6dc298cfca695c5cb71a520288b20f4f29ec8df8138724b97c4)
+// Input contract: 0.1.0 (sha256:3436eada52ceea48f4c50f40195cba02bec37fbbff4ea8f5a332133e6fcde962)
 // Options: ticket-objective-merge-request-browser-operation-schema-closure,openapi-3.1,strict-integer-ranges,sorted-output
 // Output: web/workspace/src/lib/generated/ticket-api.ts
 // Regenerate/check: cargo run -q -p server-api --example generate_ticket_api_types -- --check
diff --git a/web/workspace/src/lib/generated/workdir-api.ts b/web/workspace/src/lib/generated/workdir-api.ts
index 02dfac558..a100e4cd6 100644
--- a/web/workspace/src/lib/generated/workdir-api.ts
+++ b/web/workspace/src/lib/generated/workdir-api.ts
@@ -1,6 +1,6 @@
 // @generated by yoi-workdir-openapi-typescript@1. Do not edit.
 // Input: openapi/server-api.json
-// Input contract: 0.1.0 (sha256:7e640cff6bdcf6dc298cfca695c5cb71a520288b20f4f29ec8df8138724b97c4)
+// Input contract: 0.1.0 (sha256:3436eada52ceea48f4c50f40195cba02bec37fbbff4ea8f5a332133e6fcde962)
 // Options: workdir-operation-schema-closure,openapi-3.1,strict-integer-ranges,sorted-output
 // Output: web/workspace/src/lib/generated/workdir-api.ts
 // Regenerate/check: cargo run -q -p server-api --example generate_workdir_api_types -- --check
@@ -33,7 +33,7 @@ export type WorkingDirectoryOccupancy = { display_name: string; linked_at: strin
 
 export type WorkingDirectoryRemovalDisposition = "removed" | "retained" | "attention_required";
 
-export type WorkingDirectoryRemovalRequest = { reason: string; };
+export type WorkingDirectoryRemovalRequest = { operation_id: string; reason: string; };
 
 export type WorkingDirectoryRemovalResponse = { disposition: WorkingDirectoryRemovalDisposition; failure_category?: string | null; retryable: boolean; working_directory_id: string; };
 
diff --git a/web/workspace/src/lib/generated/worker-launch-api.ts b/web/workspace/src/lib/generated/worker-launch-api.ts
index 19536c02c..01acaa036 100644
--- a/web/workspace/src/lib/generated/worker-launch-api.ts
+++ b/web/workspace/src/lib/generated/worker-launch-api.ts
@@ -1,6 +1,6 @@
 // @generated by yoi-worker-openapi-typescript@1. Do not edit.
 // Input: openapi/server-api.json
-// Input contract: 0.1.0 (sha256:7e640cff6bdcf6dc298cfca695c5cb71a520288b20f4f29ec8df8138724b97c4)
+// Input contract: 0.1.0 (sha256:3436eada52ceea48f4c50f40195cba02bec37fbbff4ea8f5a332133e6fcde962)
 // Options: worker-operation-schema-closure,openapi-3.1,strict-integer-ranges,sorted-output
 // Output: web/workspace/src/lib/generated/worker-launch-api.ts
 // Regenerate/check: cargo run -q -p server-api --example generate_worker_launch_api_types -- --check
diff --git a/web/workspace/src/lib/workspace/settings/workdir-removal.ts b/web/workspace/src/lib/workspace/settings/workdir-removal.ts
index 4c7194e86..faace48b6 100644
--- a/web/workspace/src/lib/workspace/settings/workdir-removal.ts
+++ b/web/workspace/src/lib/workspace/settings/workdir-removal.ts
@@ -30,7 +30,9 @@ const causes: Readonly<Record<string, string>> = {
   provider_observation_unknown:
     "The provider could not confirm the remaining Workdir. Restore provider access so the next removal can recheck its current contents.",
   provider_cleanup_outcome_unknown:
-    "The provider has not confirmed deletion. Restore provider access and retry the same removal request to recheck the remaining target. The Workdir stays listed until deletion is confirmed.",
+    "The provider has not confirmed deletion. Restore provider access and reconcile the same request. Recovery only observes the target; it never repeats deletion.",
+  request_interrupted:
+    "The request was interrupted before execution. Submit a new request if removal is still wanted.",
   authority_invalid:
     "The removal authority could not be verified. Ask the Workspace administrator to verify the Workdir target and owning Runtime before requesting removal again.",
   provider_identity_changed:
@@ -125,11 +127,39 @@ async function removalBody(response: Response): Promise<string> {
   }
 }
 
+// 要求IDは結果不明時だけ保持する。確定した失敗の次の明示要求は別IDとなる。
+export class WorkdirRemovalRequests {
+  private readonly unresolved = new Map<string, string>();
+
+  async remove(
+    fetchFn: typeof fetch,
+    workspaceId: string,
+    runtimeId: string,
+    workdirId: string,
+  ): Promise<WorkingDirectoryRemovalResponse> {
+    const key = JSON.stringify([workspaceId, runtimeId, workdirId]);
+    const operationId = this.unresolved.get(key) ?? crypto.randomUUID();
+    this.unresolved.set(key, operationId);
+    const result = await removeWorkdir(
+      fetchFn,
+      workspaceId,
+      runtimeId,
+      workdirId,
+      operationId,
+    );
+    if (result.failure_category !== "provider_cleanup_outcome_unknown") {
+      this.unresolved.delete(key);
+    }
+    return result;
+  }
+}
+
 export async function removeWorkdir(
   fetchFn: typeof fetch,
   workspaceId: string,
   runtimeId: string,
   workdirId: string,
+  operationId: string,
 ): Promise<WorkingDirectoryRemovalResponse> {
   const response = await fetchFn(
     workspaceApiPath(
@@ -141,8 +171,10 @@ export async function removeWorkdir(
     {
       method: "DELETE",
       headers: { "content-type": "application/json" },
-      // An ordinary repeated request uses the existing durable Backend removal authority.
-      body: JSON.stringify({ reason: "User requested Workdir deletion" }),
+      body: JSON.stringify({
+        operation_id: operationId,
+        reason: "User requested Workdir deletion",
+      }),
     },
   );
   if (!response.ok) {
diff --git a/web/workspace/src/routes/w/[workspaceId]/settings/runtimes/[runtimeId]/workdirs/PageContent.svelte b/web/workspace/src/routes/w/[workspaceId]/settings/runtimes/[runtimeId]/workdirs/PageContent.svelte
index eaf74d5f0..07c10039e 100644
--- a/web/workspace/src/routes/w/[workspaceId]/settings/runtimes/[runtimeId]/workdirs/PageContent.svelte
+++ b/web/workspace/src/routes/w/[workspaceId]/settings/runtimes/[runtimeId]/workdirs/PageContent.svelte
@@ -2,7 +2,7 @@
   import { loadJson, workspaceApiPath } from '#lib/workspace/api/http.ts';
   import { parseRuntimeCleanupPlan } from '#lib/workspace/api/runtime-workers.ts';
   import { parseWorkingDirectoryListResponse } from '#lib/workspace/api/workdirs.ts';
-  import { canRemoveWorkdir, removalCause, removalGuard, removeWorkdir, WorkdirRemovalError } from '#lib/workspace/settings/workdir-removal.ts';
+  import { canRemoveWorkdir, removalCause, removalGuard, WorkdirRemovalRequests, WorkdirRemovalError } from '#lib/workspace/settings/workdir-removal.ts';
   import { formatCurrentWorkdirCheckout } from '#lib/workspace/settings/workdir-checkout.ts';
   import type { CleanupWorkdirCandidate, RuntimeCleanupPlanResponse, WorkingDirectorySummary } from '#lib/workspace/sidebar/types.ts';
   import type { PageData as RouteData } from './$types';
@@ -10,6 +10,7 @@
   type PageProps = { data: ResolvedPageData<RouteData> };
 
   let { data }: PageProps = $props();
+  const removalRequests = new WorkdirRemovalRequests();
   let cleanupBusyTarget = $state<string | null>(null);
   let refreshing = $state(false);
   let refreshError = $state<string | null>(null);
@@ -72,7 +73,7 @@
     cleanupBusyTarget = workdir.working_directory_id;
     feedback = null;
     try {
-      const result = await removeWorkdir(fetch, workspaceId, runtimeId, workdir.working_directory_id);
+      const result = await removalRequests.remove(fetch, workspaceId, runtimeId, workdir.working_directory_id);
       if (workspaceId !== data.workspaceId || runtimeId !== data.runtimeId) return;
       feedback = {
         id: workdir.working_directory_id,
diff --git a/web/workspace/tests/workdir-removal.test.ts b/web/workspace/tests/workdir-removal.test.ts
index 97dfe4aa0..dd3aa422c 100644
--- a/web/workspace/tests/workdir-removal.test.ts
+++ b/web/workspace/tests/workdir-removal.test.ts
@@ -6,6 +6,7 @@ import {
   canRemoveWorkdir,
   removalCause,
   removeWorkdir,
+  WorkdirRemovalRequests,
 } from "../src/lib/workspace/settings/workdir-removal.ts";
 import type {
   CleanupWorkdirCandidate,
@@ -57,6 +58,7 @@ Deno.test("removal wire boundary rejects malformed results and mismatched identi
       "workspace",
       "runtime",
       "dir",
+      "request-1",
     );
   } catch {
     rejected = true;
@@ -72,6 +74,7 @@ Deno.test("removal response size is bounded before decoding provider content", a
       "workspace",
       "runtime",
       "dir",
+      "request-1",
     );
   } catch {
     rejected = true;
@@ -179,7 +182,7 @@ Deno.test("pending unknown cleanup permits ordinary removal while current dirty
   );
 });
 
-Deno.test("ordinary retries send the same scoped DELETE body and expose only allowlisted HTTP causes", async () => {
+Deno.test("new requests after confirmed failure get distinct IDs and expose only allowlisted HTTP causes", async () => {
   const requests: { path: string; body: string; method: string }[] = [];
   const fetchFn = (async (path: RequestInfo | URL, init?: RequestInit) => {
     requests.push({
@@ -194,8 +197,9 @@ Deno.test("ordinary retries send the same scoped DELETE body and expose only all
       failure_category: "mount_present",
     });
   }) as typeof fetch;
+  const removalRequests = new WorkdirRemovalRequests();
   for (let i = 0; i < 2; i++) {
-    const result = await removeWorkdir(
+    const result = await removalRequests.remove(
       fetchFn,
       "workspace/x",
       "runtime/x",
@@ -204,8 +208,9 @@ Deno.test("ordinary retries send the same scoped DELETE body and expose only all
     assert(result.retryable && result.failure_category === "mount_present");
   }
   assert(
-    JSON.stringify(requests[0]) === JSON.stringify(requests[1]),
-    "retry changed ordinary deletion request",
+    JSON.parse(requests[0].body).operation_id !==
+      JSON.parse(requests[1].body).operation_id,
+    "new explicit request reused a failed request identity",
   );
   assert(
     requests[0].path ===
@@ -213,8 +218,9 @@ Deno.test("ordinary retries send the same scoped DELETE body and expose only all
   );
   assert(
     requests[0].method === "DELETE" &&
-      requests[0].body ===
-        JSON.stringify({ reason: "User requested Workdir deletion" }),
+      JSON.parse(requests[0].body).reason ===
+        "User requested Workdir deletion" &&
+      typeof JSON.parse(requests[0].body).operation_id === "string",
   );
   for (
     const [status, category] of [
@@ -236,6 +242,7 @@ Deno.test("ordinary retries send the same scoped DELETE body and expose only all
         "workspace",
         "runtime",
         "dir",
+        "request-1",
       );
     } catch (error) {
       message = error instanceof Error ? error.message : String(error);
@@ -246,3 +253,34 @@ Deno.test("ordinary retries send the same scoped DELETE body and expose only all
     );
   }
 });
+
+Deno.test("unknown removal outcomes keep the same identity and body until a terminal result", async () => {
+  for (const transportLoss of [false, true]) {
+    const calls: string[] = [];
+    const requester = new WorkdirRemovalRequests();
+    const fetchFn = (async (_path: RequestInfo | URL, init?: RequestInit) => {
+      calls.push(String(init?.body));
+      if (calls.length === 1 && transportLoss) {
+        throw new Error("connection lost");
+      }
+      return Response.json({
+        working_directory_id: "dir",
+        disposition: "attention_required",
+        retryable: calls.length !== 1,
+        failure_category: calls.length === 1
+          ? "provider_cleanup_outcome_unknown"
+          : "resource_busy",
+      });
+    }) as typeof fetch;
+    await requester.remove(fetchFn, "workspace", "runtime", "dir").catch(() =>
+      undefined
+    );
+    await requester.remove(fetchFn, "workspace", "runtime", "dir");
+    await requester.remove(fetchFn, "workspace", "runtime", "dir");
+    assert(calls[0] === calls[1], "unknown outcome changed request identity");
+    assert(
+      calls[1] !== calls[2],
+      "confirmed failure kept old request identity",
+    );
+  }
+});