diff --git a/apps/ui/src/components/views/board-view.tsx b/apps/ui/src/components/views/board-view.tsx
index 046ab4bd..7928c21c 100644
--- a/apps/ui/src/components/views/board-view.tsx
+++ b/apps/ui/src/components/views/board-view.tsx
@@ -521,9 +521,9 @@ export function BoardView() {
           // Empty string clears the branch assignment, moving features to main/current branch
           finalBranchName = '';
         } else if (workMode === 'auto') {
-          // Auto-generate a branch name based on current branch and timestamp
-          const baseBranch =
-            currentWorktreeBranch || getPrimaryWorktreeBranch(currentProject.path) || 'main';
+          // Auto-generate a branch name based on primary branch (main/master) and timestamp
+          // Always use primary branch to avoid nested feature/feature/... paths
+          const baseBranch = getPrimaryWorktreeBranch(currentProject.path) || 'main';
           const timestamp = Date.now();
           const randomSuffix = Math.random().toString(36).substring(2, 6);
           finalBranchName = `feature/${baseBranch}-${timestamp}-${randomSuffix}`;
@@ -603,7 +603,6 @@ export function BoardView() {
       selectedFeatureIds,
       updateFeature,
       exitSelectionMode,
-      currentWorktreeBranch,
       getPrimaryWorktreeBranch,
       addAndSelectWorktree,
       setWorktreeRefreshKey,
diff --git a/apps/ui/src/components/views/board-view/hooks/use-board-actions.ts b/apps/ui/src/components/views/board-view/hooks/use-board-actions.ts
index ac39af5e..c9aba757 100644
--- a/apps/ui/src/components/views/board-view/hooks/use-board-actions.ts
+++ b/apps/ui/src/components/views/board-view/hooks/use-board-actions.ts
@@ -127,8 +127,10 @@ export function useBoardActions({
         // No worktree isolation - work directly on current branch
         finalBranchName = undefined;
       } else if (workMode === 'auto') {
-        // Auto-generate a branch name based on current branch and timestamp
-        const baseBranch = currentWorktreeBranch || 'main';
+        // Auto-generate a branch name based on primary branch (main/master) and timestamp
+        // Always use primary branch to avoid nested feature/feature/... paths
+        const baseBranch =
+          (currentProject?.path ? getPrimaryWorktreeBranch(currentProject.path) : null) || 'main';
         const timestamp = Date.now();
         const randomSuffix = Math.random().toString(36).substring(2, 6);
         finalBranchName = `feature/${baseBranch}-${timestamp}-${randomSuffix}`;
@@ -245,7 +247,7 @@ export function useBoardActions({
       currentProject,
       onWorktreeCreated,
       onWorktreeAutoSelect,
-      currentWorktreeBranch,
+      getPrimaryWorktreeBranch,
       features,
     ]
   );
@@ -282,7 +284,10 @@ export function useBoardActions({
       if (workMode === 'current') {
         finalBranchName = undefined;
       } else if (workMode === 'auto') {
-        const baseBranch = currentWorktreeBranch || 'main';
+        // Auto-generate a branch name based on primary branch (main/master) and timestamp
+        // Always use primary branch to avoid nested feature/feature/... paths
+        const baseBranch =
+          (currentProject?.path ? getPrimaryWorktreeBranch(currentProject.path) : null) || 'main';
         const timestamp = Date.now();
         const randomSuffix = Math.random().toString(36).substring(2, 6);
         finalBranchName = `feature/${baseBranch}-${timestamp}-${randomSuffix}`;
@@ -390,7 +395,7 @@ export function useBoardActions({
       setEditingFeature,
       currentProject,
       onWorktreeCreated,
-      currentWorktreeBranch,
+      getPrimaryWorktreeBranch,
       features,
     ]
   );