diff --git a/apps/workspace-engine/pkg/jobagents/argo/application_upserter.go b/apps/workspace-engine/pkg/jobagents/argo/application_upserter.go
index 7c02b510d..90ed77710 100644
--- a/apps/workspace-engine/pkg/jobagents/argo/application_upserter.go
+++ b/apps/workspace-engine/pkg/jobagents/argo/application_upserter.go
@@ -2,6 +2,7 @@ package argo
 
 import (
 	"context"
+	"errors"
 	"fmt"
 	"log/slog"
 	"strings"
@@ -76,6 +77,9 @@ func isRetryableError(err error) bool {
 	if err == nil {
 		return false
 	}
+	if errors.Is(err, context.DeadlineExceeded) {
+		return true
+	}
 	errStr := err.Error()
 	return strings.Contains(errStr, "502") ||
 		strings.Contains(errStr, "503") ||
@@ -85,7 +89,8 @@ func isRetryableError(err error) bool {
 		strings.Contains(errStr, "timeout") ||
 		strings.Contains(errStr, "temporarily unavailable") ||
 		strings.Contains(errStr, "EOF") ||
-		strings.Contains(errStr, "Unavailable")
+		strings.Contains(errStr, "Unavailable") ||
+		strings.Contains(errStr, "context deadline exceeded")
 }
 
 // GoApplicationDeleter is the production implementation of
diff --git a/apps/workspace-engine/pkg/jobagents/argo/argoapp_test.go b/apps/workspace-engine/pkg/jobagents/argo/argoapp_test.go
index 3d5133ca3..62eef6e12 100644
--- a/apps/workspace-engine/pkg/jobagents/argo/argoapp_test.go
+++ b/apps/workspace-engine/pkg/jobagents/argo/argoapp_test.go
@@ -637,6 +637,12 @@ func TestIsRetryableError(t *testing.T) {
 		{"Unavailable", fmt.Errorf("Unavailable"), true},
 		{"not found", fmt.Errorf("application not found"), false},
 		{"permission denied", fmt.Errorf("permission denied"), false},
+		{"context deadline exceeded sentinel", context.DeadlineExceeded, true},
+		{
+			"context deadline exceeded grpc status",
+			status.Error(codes.DeadlineExceeded, "context deadline exceeded"),
+			true,
+		},
 	}
 
 	for _, tt := range tests {