diff --git a/crates/workspace-server/src/retention.rs b/crates/workspace-server/src/retention.rs
index f4e06eb6..6e9e5751 100644
--- a/crates/workspace-server/src/retention.rs
+++ b/crates/workspace-server/src/retention.rs
@@ -106,12 +106,15 @@ pub struct WorkerRemovalPlan {
     pub reason: String,
     pub created_at: String,
     pub updated_at: String,
+    #[serde(skip_serializing_if = "Option::is_none")]
+    pub failure_category: Option<String>,
 }
 
 #[derive(Clone, Debug, PartialEq, Eq, Serialize, Deserialize)]
 pub struct PreparedWorkerRemoval {
     pub plan: WorkerRemovalPlan,
     pub runtime_request: WorkerRetentionExecutionRequest,
+    pub prior_failure_category: Option<String>,
 }
 
 #[derive(Clone, Debug, PartialEq, Eq, Serialize, Deserialize)]
@@ -369,6 +372,7 @@ impl SqliteWorkspaceStore {
             )
         })?;
         let removed_at = plan.created_at.clone();
+        let prior_failure_category = plan.failure_category.clone();
         Ok(PreparedWorkerRemoval {
             runtime_request: WorkerRetentionExecutionRequest {
                 operation_id: plan.operation_id.clone(),
@@ -389,6 +393,7 @@ impl SqliteWorkspaceStore {
                 diagnostics_disposition: plan.diagnostics_disposition,
             },
             plan,
+            prior_failure_category,
         })
     }
 
@@ -429,6 +434,7 @@ impl SqliteWorkspaceStore {
         let Some(plan) = plan else {
             return Ok(None);
         };
+        let prior_failure_category = plan.failure_category.clone();
         let worker_number = plan.worker.worker_id.parse::<u64>().map_err(|_| {
             WorkerRetentionError::Invalid(
                 "Runtime Worker id is not a canonical unsigned integer".to_string(),
@@ -468,6 +474,7 @@ impl SqliteWorkspaceStore {
                 diagnostics_disposition: plan.diagnostics_disposition,
             },
             plan,
+            prior_failure_category,
         }))
     }
 
@@ -758,7 +765,7 @@ fn load_plan_q(c: &Connection, key: &str, id: &str) -> crate::Result<Option<Work
                 worker_revision,run_generation,policy_id,policy_revision,session_disposition,
                 metadata_disposition,archive_retention_kind,archive_retention_seconds,
                 diagnostics_disposition,diagnostics_retention_seconds,archive_id,blockers_json,
-                state,reason,created_at,updated_at
+                state,reason,created_at,updated_at,failure_category
          FROM worker_removal_operations WHERE {key}=?1"
     );
     c.query_row(&query, params![id], |row| {
@@ -799,6 +806,7 @@ fn load_plan_q(c: &Connection, key: &str, id: &str) -> crate::Result<Option<Work
             reason: row.get(19)?,
             created_at: row.get(20)?,
             updated_at: row.get(21)?,
+            failure_category: row.get(22)?,
         })
     })
     .optional()
@@ -1532,6 +1540,36 @@ mod tests {
         );
     }
 
+    #[test]
+    fn recovery_preserves_attachment_failure_stage_for_retry_ordering() {
+        let s = setup();
+        let request = req();
+        let plan = s.plan_worker_removal(&request, &inv()).unwrap();
+        s.prepare_worker_removal_execution("w", &plan.plan_id, &plan.input_fingerprint)
+            .unwrap();
+        s.fail_worker_removal(
+            "w",
+            &plan.operation_id,
+            &plan.input_fingerprint,
+            "workdir_attachment_release_failed",
+        )
+        .unwrap();
+        let recovered = s
+            .recover_worker_removal_execution(
+                "w",
+                &request.worker,
+                &request.expected_worker_revision,
+                &request.reason,
+            )
+            .unwrap()
+            .unwrap();
+        assert_eq!(
+            recovered.prior_failure_category.as_deref(),
+            Some("workdir_attachment_release_failed")
+        );
+        assert_eq!(recovered.plan.state, WorkerRemovalPlanState::Failed);
+    }
+
     #[test]
     fn old_schema_upgrade_seeds_existing_workspace() {
         let temp = tempfile::tempdir().unwrap();
diff --git a/crates/workspace-server/src/server.rs b/crates/workspace-server/src/server.rs
index f65acf93..5abd8a82 100644
--- a/crates/workspace-server/src/server.rs
+++ b/crates/workspace-server/src/server.rs
@@ -396,6 +396,11 @@ impl WorkspaceWorkerRemoveExecutor {
             if prepared.plan.state == crate::retention::WorkerRemovalPlanState::Succeeded {
                 return Ok(worker_remove_success_response(&target));
             }
+            let must_close_session =
+                prepared.prior_failure_category.as_deref() == Some("workdir_session_close_failed");
+            let must_release_attachment = must_close_session
+                || prepared.prior_failure_category.as_deref()
+                    == Some("workdir_attachment_release_failed");
             let prepared =
                 if prepared.plan.state == crate::retention::WorkerRemovalPlanState::Failed {
                     match self.store.prepare_worker_removal_execution(
@@ -409,6 +414,57 @@ impl WorkspaceWorkerRemoveExecutor {
                 } else {
                     prepared
                 };
+            if must_close_session {
+                let session = {
+                    self.workdir_sessions
+                        .lock()
+                        .map_err(|_| "Workdir session registry was poisoned".to_string())?
+                        .get(&target)
+                        .cloned()
+                };
+                if let Some(session) = session {
+                    if session.close().await.is_err() {
+                        let _ = self.store.fail_worker_removal(
+                            &self.workspace_id,
+                            &prepared.plan.operation_id,
+                            &prepared.plan.input_fingerprint,
+                            "workdir_session_close_failed",
+                        );
+                        return Ok(worker_remove_error_response(
+                            StatusCode::SERVICE_UNAVAILABLE,
+                            "attachment_close_failed",
+                            "Worker Workdir session could not be closed; removal can be retried",
+                        ));
+                    }
+                    self.workdir_sessions
+                        .lock()
+                        .map_err(|_| "Workdir session registry was poisoned".to_string())?
+                        .remove(&target);
+                }
+            }
+            if must_release_attachment
+                && self
+                    .store
+                    .detach_worker_workdir(
+                        &self.workspace_id,
+                        &target,
+                        None,
+                        &Utc::now().to_rfc3339_opts(SecondsFormat::Millis, true),
+                    )
+                    .is_err()
+            {
+                let _ = self.store.fail_worker_removal(
+                    &self.workspace_id,
+                    &prepared.plan.operation_id,
+                    &prepared.plan.input_fingerprint,
+                    "workdir_attachment_release_failed",
+                );
+                return Ok(worker_remove_error_response(
+                    StatusCode::SERVICE_UNAVAILABLE,
+                    "attachment_release_failed",
+                    "Worker Workdir attachment could not be released; removal can be retried",
+                ));
+            }
             return self
                 .resume_worker_retention(&runtime, &target, prepared)
                 .await;