diff --git a/frontend/src/components/NormalizedConversation/PendingApprovalEntry.tsx b/frontend/src/components/NormalizedConversation/PendingApprovalEntry.tsx
index a3b45ce8..78816d96 100644
--- a/frontend/src/components/NormalizedConversation/PendingApprovalEntry.tsx
+++ b/frontend/src/components/NormalizedConversation/PendingApprovalEntry.tsx
@@ -147,20 +147,18 @@ function DenyReasonForm({
         disabled={isResponding}
         className="text-sm"
       />
-      <div className="mt-3 flex flex-wrap items-center justify-between gap-2">
-        <div className="flex items-center gap-2 text-sm">
-          <Button
-            variant="ghost"
-            size="sm"
-            onClick={onCancel}
-            disabled={isResponding}
-          >
-            Cancel
-          </Button>
-          <Button size="sm" onClick={onSubmit} disabled={isResponding}>
-            Deny
-          </Button>
-        </div>
+      <div className="mt-3 flex flex-wrap items-center justify-end gap-2">
+        <Button
+          variant="ghost"
+          size="sm"
+          onClick={onCancel}
+          disabled={isResponding}
+        >
+          Cancel
+        </Button>
+        <Button size="sm" onClick={onSubmit} disabled={isResponding}>
+          Deny
+        </Button>
       </div>
     </div>
   );
diff --git a/frontend/src/hooks/useConversationHistory.ts b/frontend/src/hooks/useConversationHistory.ts
index e090b689..f049584f 100644
--- a/frontend/src/hooks/useConversationHistory.ts
+++ b/frontend/src/hooks/useConversationHistory.ts
@@ -255,10 +255,22 @@ export const useConversationHistory = ({
               e.type !== 'NORMALIZED_ENTRY' ||
               e.content.entry_type.type !== 'user_message'
           );
+
+          const hasPendingApprovalEntry = entriesExcludingUser.some((entry) => {
+            if (entry.type !== 'NORMALIZED_ENTRY') return false;
+            const entryType = entry.content.entry_type;
+            return (
+              entryType.type === 'tool_use' &&
+              entryType.status.status === 'pending_approval'
+            );
+          });
+
           entries.push(...entriesExcludingUser);
-          if (
-            getLiveExecutionProcess(p.executionProcess.id)?.status === 'running'
-          ) {
+          const isProcessRunning =
+            getLiveExecutionProcess(p.executionProcess.id)?.status ===
+            'running';
+
+          if (isProcessRunning && !hasPendingApprovalEntry) {
             entries.push(loadingPatch);
           }
         } else if (