fix: preserve workdir failure diagnostics across transport

crates/tools/src/bash.rs

@@ -158,11 +158,15 @@ async fn command_page(
 ) -> Result<workdir::CommandOutput, workdir::WorkdirError> {
     for attempt in 0..3 {
         match session.command_output(request.clone()).await {
-            Err(
-                workdir::WorkdirError::Transport(_)
-                | workdir::WorkdirError::Unavailable(_)
-                | workdir::WorkdirError::OutcomeUnknown(_),
-            ) if attempt < 2 => {
+            Err(error)
+                if attempt < 2
+                    && matches!(
+                        error.classification_source(),
+                        workdir::WorkdirError::Transport(_)
+                            | workdir::WorkdirError::Unavailable(_)
+                            | workdir::WorkdirError::OutcomeUnknown(_)
+                    ) =>
+            {
                 tokio::time::sleep(std::time::Duration::from_millis(100 << attempt)).await;
             }
             result => return result,

crates/tools/src/file_target.rs

@@ -147,7 +147,9 @@ impl FileTarget {
 pub(crate) fn checked_error(error: workdir::WorkdirError) -> ToolError {
     use workdir::WorkdirError;
     let code = match error.classification_source() {
-        WorkdirError::DenialContext { .. } => unreachable!("diagnostic context unwrapped"),
+        WorkdirError::DenialContext { .. } | WorkdirError::FailureContext { .. } => {
+            unreachable!("diagnostic context unwrapped")
+        }
         WorkdirError::Conflict(_) | WorkdirError::NotFound(_) => "checkout_stale",
         WorkdirError::Denied { .. }
         | WorkdirError::OutOfScope { .. }

crates/tools/tests/integration.rs

@@ -546,9 +546,10 @@ impl workdir::WorkdirSession for ExternalValidatingSession {
                 .is_ok()
         {
             // The production provider has committed a page, but its response is lost.
-            return Err(workdir::WorkdirError::Transport(
-                "injected lost response".into(),
-            ));
+            return Err(
+                workdir::WorkdirError::Transport("injected lost response".into())
+                    .with_failure_reason(workdir::WorkdirFailureReason::HttpTimeout),
+            );
         }
         Ok(output)
     }