diff --git a/frontend/src/components/tasks/TaskDetailsToolbar.tsx b/frontend/src/components/tasks/TaskDetailsToolbar.tsx
index bccecb2b..86eb77a8 100644
--- a/frontend/src/components/tasks/TaskDetailsToolbar.tsx
+++ b/frontend/src/components/tasks/TaskDetailsToolbar.tsx
@@ -148,6 +148,33 @@ export function TaskDetailsToolbar({
     setIsInCreateAttemptMode(taskAttempts.length === 0);
   }, [taskAttempts.length]);
 
+  // Update default values from latest attempt when taskAttempts change
+  useEffect(() => {
+    if (taskAttempts.length > 0) {
+      const latestAttempt = taskAttempts.reduce((latest, current) =>
+        new Date(current.created_at) > new Date(latest.created_at)
+          ? current
+          : latest
+      );
+
+      // Only update if branch still exists in available branches
+      if (
+        latestAttempt.base_branch &&
+        branches.some((b: GitBranch) => b.name === latestAttempt.base_branch)
+      ) {
+        setCreateAttemptBranch(latestAttempt.base_branch);
+      }
+
+      // Only update executor if it's different from default and exists in available executors
+      if (
+        latestAttempt.executor &&
+        availableExecutors.some((e) => e.id === latestAttempt.executor)
+      ) {
+        setCreateAttemptExecutor(latestAttempt.executor);
+      }
+    }
+  }, [taskAttempts, branches, availableExecutors]);
+
   // Update PR base branch when selected attempt changes
   useEffect(() => {
     if (selectedAttempt?.base_branch) {
@@ -349,8 +376,39 @@ export function TaskDetailsToolbar({
   // Handle entering create attempt mode
   const handleEnterCreateAttemptMode = () => {
     setIsInCreateAttemptMode(true);
-    setCreateAttemptBranch(selectedBranch);
-    setCreateAttemptExecutor(selectedExecutor);
+
+    // Use latest attempt's settings as defaults if available
+    if (taskAttempts.length > 0) {
+      const latestAttempt = taskAttempts.reduce((latest, current) =>
+        new Date(current.created_at) > new Date(latest.created_at)
+          ? current
+          : latest
+      );
+
+      // Use latest attempt's branch if it still exists, otherwise use current selected branch
+      if (
+        latestAttempt.base_branch &&
+        branches.some((b: GitBranch) => b.name === latestAttempt.base_branch)
+      ) {
+        setCreateAttemptBranch(latestAttempt.base_branch);
+      } else {
+        setCreateAttemptBranch(selectedBranch);
+      }
+
+      // Use latest attempt's executor if it exists, otherwise use current selected executor
+      if (
+        latestAttempt.executor &&
+        availableExecutors.some((e) => e.id === latestAttempt.executor)
+      ) {
+        setCreateAttemptExecutor(latestAttempt.executor);
+      } else {
+        setCreateAttemptExecutor(selectedExecutor);
+      }
+    } else {
+      // Fallback to current selected values if no attempts exist
+      setCreateAttemptBranch(selectedBranch);
+      setCreateAttemptExecutor(selectedExecutor);
+    }
   };
 
   // Handle exiting create attempt mode