diff --git a/pkg/cli/logs_orchestrator_download.go b/pkg/cli/logs_orchestrator_download.go
index 683a0908cab..62304dec6d3 100644
--- a/pkg/cli/logs_orchestrator_download.go
+++ b/pkg/cli/logs_orchestrator_download.go
@@ -422,7 +422,7 @@ func appendProcessedWorkflowRuns(
 		if shouldSkipProcessedWorkflowRun(result, opts.verbose) || applyRunFilters(activeCtx, result, opts.filters, opts.verbose) {
 			continue
 		}
-		processedRun := buildProcessedRun(result, opts.verbose, true)
+		processedRun := buildProcessedRun(activeCtx, result, opts.verbose, true)
 		parseWorkflowRunArtifacts(result, processedRun, opts.parse, opts.verbose)
 		processedRuns = append(processedRuns, processedRun)
 		batchProcessed++
diff --git a/pkg/cli/logs_orchestrator_filters.go b/pkg/cli/logs_orchestrator_filters.go
index 62c285cf030..3fa97adb698 100644
--- a/pkg/cli/logs_orchestrator_filters.go
+++ b/pkg/cli/logs_orchestrator_filters.go
@@ -149,7 +149,7 @@ func applyRunFilters(ctx context.Context, result DownloadResult, opts runFilterO
 
 // buildProcessedRun constructs a ProcessedRun from a DownloadResult, computing
 // duration, action minutes, effective tokens, and job-failure counts.
-func buildProcessedRun(result DownloadResult, verbose, logFailedJobs bool) ProcessedRun {
+func buildProcessedRun(ctx context.Context, result DownloadResult, verbose, logFailedJobs bool) ProcessedRun {
 	run := result.Run
 	run.TokenUsage = result.Metrics.TokenUsage
 	applyMetricsTurnsToRun(&run, result.Metrics)
@@ -164,7 +164,7 @@ func buildProcessedRun(result DownloadResult, verbose, logFailedJobs bool) Proce
 	}
 
 	// Add failed jobs to error count.
-	if failedJobCount, err := fetchJobStatusesForProcessedRun(context.Background(), run.DatabaseID, verbose); err == nil {
+	if failedJobCount, err := fetchJobStatusesForProcessedRun(ctx, run.DatabaseID, verbose); err == nil {
 		run.ErrorCount += failedJobCount
 		if verbose && logFailedJobs && failedJobCount > 0 {
 			fmt.Fprintln(os.Stderr, console.FormatInfoMessage(fmt.Sprintf("Added %d failed jobs to error count for run %d", failedJobCount, run.DatabaseID)))
diff --git a/pkg/cli/logs_orchestrator_filters_test.go b/pkg/cli/logs_orchestrator_filters_test.go
index 285eee2e652..42c5b941b1f 100644
--- a/pkg/cli/logs_orchestrator_filters_test.go
+++ b/pkg/cli/logs_orchestrator_filters_test.go
@@ -225,7 +225,7 @@ func TestBuildProcessedRun(t *testing.T) {
 			AwContext: awCtx,
 		}
 
-		pr := buildProcessedRun(result, false, false)
+		pr := buildProcessedRun(context.Background(), result, false, false)
 
 		assert.Equal(t, int64(1234), pr.Run.DatabaseID)
 		assert.Equal(t, tmpDir, pr.Run.LogsPath)
@@ -246,7 +246,7 @@ func TestBuildProcessedRun(t *testing.T) {
 			LogsPath: t.TempDir(),
 		}
 
-		pr := buildProcessedRun(result, false, false)
+		pr := buildProcessedRun(context.Background(), result, false, false)
 
 		assert.Equal(t, 90*time.Second, pr.Run.Duration)
 		assert.InDelta(t, 2.0, pr.Run.ActionMinutes, 0.001) // ceil(1.5) = 2
@@ -258,7 +258,7 @@ func TestBuildProcessedRun(t *testing.T) {
 			Run:      WorkflowRun{DatabaseID: 7},
 			LogsPath: t.TempDir(),
 		}
-		pr := buildProcessedRun(result, false, false)
+		pr := buildProcessedRun(context.Background(), result, false, false)
 		assert.Equal(t, time.Duration(0), pr.Run.Duration)
 		assert.InDelta(t, 0.0, pr.Run.ActionMinutes, 0.001)
 	})
@@ -271,7 +271,7 @@ func TestBuildProcessedRun(t *testing.T) {
 			LogsPath:   t.TempDir(),
 			TokenUsage: usage,
 		}
-		pr := buildProcessedRun(result, false, false)
+		pr := buildProcessedRun(context.Background(), result, false, false)
 		assert.Equal(t, 5000, pr.Run.EffectiveTokens)
 	})
 
@@ -283,14 +283,19 @@ func TestBuildProcessedRun(t *testing.T) {
 			LogsPath:   t.TempDir(),
 			TokenUsage: usage,
 		}
-		pr := buildProcessedRun(result, false, false)
+		pr := buildProcessedRun(context.Background(), result, false, false)
 		assert.Equal(t, 0, pr.Run.EffectiveTokens)
 	})
 
 	t.Run("failed job count is added via test seam", func(t *testing.T) {
-		stubFetchJobStatusesForProcessedRun(t, func(_ context.Context, runID int64, verbose bool) (int, error) {
+		type ctxKey string
+		const key ctxKey = "request-id"
+		ctx := context.WithValue(context.Background(), key, "abc123")
+
+		stubFetchJobStatusesForProcessedRun(t, func(fetchCtx context.Context, runID int64, verbose bool) (int, error) {
 			assert.Equal(t, int64(88), runID)
 			assert.False(t, verbose)
+			assert.Equal(t, "abc123", fetchCtx.Value(key))
 			return 2, nil
 		})
 		result := DownloadResult{
@@ -298,7 +303,7 @@ func TestBuildProcessedRun(t *testing.T) {
 			LogsPath: t.TempDir(),
 		}
 
-		pr := buildProcessedRun(result, false, false)
+		pr := buildProcessedRun(ctx, result, false, false)
 
 		assert.Equal(t, 2, pr.Run.ErrorCount)
 	})
diff --git a/pkg/cli/logs_orchestrator_stdin.go b/pkg/cli/logs_orchestrator_stdin.go
index 9c907502a53..a9877019d0c 100644
--- a/pkg/cli/logs_orchestrator_stdin.go
+++ b/pkg/cli/logs_orchestrator_stdin.go
@@ -178,7 +178,7 @@ func DownloadWorkflowLogsFromStdin(ctx context.Context, opts StdinLogsOptions) e
 			continue
 		}
 
-		processedRun := buildProcessedRun(result, opts.Verbose, false)
+		processedRun := buildProcessedRun(ctx, result, opts.Verbose, false)
 
 		if opts.Parse {
 			awInfoPath := filepath.Join(result.LogsPath, "aw_info.json")
diff --git a/pkg/cli/update_extension_check.go b/pkg/cli/update_extension_check.go
index 3725a75d514..cbb522d8922 100644
--- a/pkg/cli/update_extension_check.go
+++ b/pkg/cli/update_extension_check.go
@@ -46,7 +46,7 @@ const backupCleanupRetryDelay = 300 * time.Millisecond
 // baked in. The caller should re-launch the freshly-installed binary (at
 // installPath) so that subsequent work (e.g. lock-file compilation) uses the
 // correct new version string.
-func upgradeExtensionIfOutdated(verbose bool, includePrereleases bool) (bool, string, error) {
+func upgradeExtensionIfOutdated(ctx context.Context, verbose bool, includePrereleases bool) (bool, string, error) {
 	currentVersion := GetVersion()
 	updateExtensionCheckLog.Printf("Checking if extension needs upgrade (current: %s)", currentVersion)
 
@@ -60,7 +60,7 @@ func upgradeExtensionIfOutdated(verbose bool, includePrereleases bool) (bool, st
 	}
 
 	// Query GitHub API for latest release
-	latestVersion, err := getLatestRelease(context.Background(), includePrereleases)
+	latestVersion, err := getLatestRelease(ctx, includePrereleases)
 	if err != nil {
 		// Fail silently - don't block the upgrade command if we can't reach GitHub
 		updateExtensionCheckLog.Printf("Failed to check for latest release (silently ignoring): %v", err)
diff --git a/pkg/cli/update_extension_check_test.go b/pkg/cli/update_extension_check_test.go
index 250893672fb..45f3cb9fd11 100644
--- a/pkg/cli/update_extension_check_test.go
+++ b/pkg/cli/update_extension_check_test.go
@@ -4,6 +4,7 @@ package cli
 
 import (
 	"bytes"
+	"context"
 	"errors"
 	"os"
 	"path/filepath"
@@ -27,7 +28,7 @@ func TestUpgradeExtensionIfOutdated_DevBuild(t *testing.T) {
 	// Verify the function exits before making any API calls.
 	// If it did make API calls we'd see a network error in test environments,
 	// but the function must return (false, "", nil) immediately.
-	upgraded, installPath, err := upgradeExtensionIfOutdated(false, false)
+	upgraded, installPath, err := upgradeExtensionIfOutdated(context.Background(), false, false)
 	require.NoError(t, err, "Should not return error for dev builds")
 	assert.False(t, upgraded, "Should not report upgrade for dev builds")
 	assert.Empty(t, installPath, "installPath should be empty for dev builds")
@@ -44,7 +45,7 @@ func TestUpgradeExtensionIfOutdated_SilentFailureOnAPIError(t *testing.T) {
 	// Use a release version so the API call is attempted
 	SetVersionInfo("v0.1.0")
 
-	upgraded, installPath, err := upgradeExtensionIfOutdated(false, false)
+	upgraded, installPath, err := upgradeExtensionIfOutdated(context.Background(), false, false)
 	require.NoError(t, err, "Should fail silently on API errors")
 	assert.False(t, upgraded, "Should not report upgrade when API is unreachable")
 	assert.Empty(t, installPath, "installPath should be empty when API is unreachable")
diff --git a/pkg/cli/upgrade_command.go b/pkg/cli/upgrade_command.go
index bb9d968f4be..e3093cfc9b7 100644
--- a/pkg/cli/upgrade_command.go
+++ b/pkg/cli/upgrade_command.go
@@ -242,7 +242,7 @@ func runUpgradeCommand(opts upgradeOptions) error {
 	// prevents the re-launched process from entering this branch again.
 	if !opts.skipExtensionUpgrade {
 		fmt.Fprintln(os.Stderr, console.FormatInfoMessage("Checking gh-aw extension version..."))
-		upgraded, installPath, err := upgradeExtensionIfOutdated(opts.verbose, opts.preReleases)
+		upgraded, installPath, err := upgradeExtensionIfOutdated(opts.ctx, opts.verbose, opts.preReleases)
 		if err != nil {
 			upgradeLog.Printf("Extension upgrade failed: %v", err)
 			return err