diff --git a/src/cli/App.tsx b/src/cli/App.tsx
index 9a8f5c9..91d6498 100644
--- a/src/cli/App.tsx
+++ b/src/cli/App.tsx
@@ -1,6 +1,8 @@
 // src/cli/App.tsx
 
 import { existsSync, readFileSync, writeFileSync } from "node:fs";
+import { homedir } from "node:os";
+import { join } from "node:path";
 import { APIError, APIUserAbortError } from "@letta-ai/letta-client/core/error";
 import type {
   AgentState,
@@ -6396,10 +6398,11 @@ DO NOT respond to these messages or otherwise consider them in your response unl
     const approval = pendingApprovals[currentIndex];
     if (approval?.toolName === "ExitPlanMode" && !planFileExists()) {
       const planFilePath = permissionMode.getPlanFilePath();
+      const plansDir = join(homedir(), ".letta", "plans");
       handlePlanKeepPlanning(
-        `You must write your plan to the plan file before exiting plan mode.\n` +
-          `Plan file path: ${planFilePath || "not set"}\n` +
-          `Use a write tool (e.g. Write, ApplyPatch, etc.) to create your plan, then call ExitPlanMode again.`,
+        `You must write your plan to a plan file before exiting plan mode.\n` +
+          (planFilePath ? `Plan file path: ${planFilePath}\n` : "") +
+          `Use a write tool to create your plan in ${plansDir}, then use ExitPlanMode to present the plan to the user.`,
       );
     }
   }, [pendingApprovals, approvalResults.length, handlePlanKeepPlanning]);
@@ -6792,6 +6795,18 @@ Plan file path: ${planFilePath}`;
                       return null;
                     }
 
+                    // Skip tool calls that were eagerly committed to staticItems
+                    // (e.g., ExitPlanMode preview) - but only AFTER approval is complete
+                    // We still need to render the approval options while awaiting approval
+                    if (
+                      ln.kind === "tool_call" &&
+                      ln.toolCallId &&
+                      eagerCommittedPreviewsRef.current.has(ln.toolCallId) &&
+                      ln.toolCallId !== currentApproval?.toolCallId
+                    ) {
+                      return null;
+                    }
+
                     // Check if this tool call matches the current ExitPlanMode approval
                     const isExitPlanModeApproval =
                       ln.kind === "tool_call" &&
diff --git a/src/permissions/mode.ts b/src/permissions/mode.ts
index b78303d..c27830f 100644
--- a/src/permissions/mode.ts
+++ b/src/permissions/mode.ts
@@ -1,6 +1,9 @@
 // src/permissions/mode.ts
 // Permission mode management (default, acceptEdits, plan, bypassPermissions)
 
+import { homedir } from "node:os";
+import { join } from "node:path";
+
 import { isReadOnlyShellCommand } from "./readOnlyShell";
 
 export type PermissionMode =
@@ -171,9 +174,12 @@ class PermissionModeManager {
           return "allow";
         }
 
-        // Special case: allow writes to the plan file only
+        // Special case: allow writes to any plan file in ~/.letta/plans/
+        // NOTE: We allow writing to ANY plan file, not just the assigned one.
+        // This is intentional - it allows the agent to "resume" planning after
+        // plan mode was exited/reset by simply writing to any plan file.
         if (writeTools.includes(toolName)) {
-          const planFilePath = this.getPlanFilePath();
+          const plansDir = join(homedir(), ".letta", "plans");
           let targetPath =
             (toolArgs?.file_path as string) || (toolArgs?.path as string);
 
@@ -192,7 +198,12 @@ class PermissionModeManager {
             }
           }
 
-          if (planFilePath && targetPath && targetPath === planFilePath) {
+          // Allow if target is any .md file in the plans directory
+          if (
+            targetPath &&
+            targetPath.startsWith(plansDir) &&
+            targetPath.endsWith(".md")
+          ) {
             return "allow";
           }
         }
diff --git a/src/tools/impl/ExitPlanMode.ts b/src/tools/impl/ExitPlanMode.ts
index c6bcaf1..9d7aea4 100644
--- a/src/tools/impl/ExitPlanMode.ts
+++ b/src/tools/impl/ExitPlanMode.ts
@@ -9,6 +9,10 @@ export async function exit_plan_mode(): Promise<{ message: string }> {
   // The UI layer checks if the plan file exists and auto-rejects if not
   return {
     message:
-      "User has approved your plan. You can now start coding.\nStart with updating your todo list if applicable",
+      "User has approved your plan. You can now start coding.\n" +
+      "Start with updating your todo list if applicable.\n\n" +
+      "Tip: If this plan will be referenced in the future by your future-self, " +
+      "other agents, or humans, consider renaming the plan file to something easily " +
+      "identifiable with a timestamp (e.g., `2026-01-auth-refactor.md`) rather than the random name.",
   };
 }