diff --git a/.changeset/allow-claude-yolo.md b/.changeset/allow-claude-yolo.md
new file mode 100644
index 00000000..49c642db
--- /dev/null
+++ b/.changeset/allow-claude-yolo.md
@@ -0,0 +1,5 @@
+---
+"stash": patch
+---
+
+feat(cli): pass `--allow-dangerously-skip-permissions` when `stash init` launches Claude Code, so the user can opt in to skip-permissions mode mid-session without relaunching. Codex and Wizard handoffs are unchanged.
diff --git a/packages/cli/src/commands/impl/steps/handoff-claude.ts b/packages/cli/src/commands/impl/steps/handoff-claude.ts
index bfb5f610..41d2c4fb 100644
--- a/packages/cli/src/commands/impl/steps/handoff-claude.ts
+++ b/packages/cli/src/commands/impl/steps/handoff-claude.ts
@@ -47,7 +47,7 @@ export const handoffClaudeStep: HandoffStep = {
           `Install: ${CLAUDE_INSTALL_URL}`,
           '',
           'Once installed, run:',
-          `  claude '${launchPrompt}'`,
+          `  claude --allow-dangerously-skip-permissions '${launchPrompt}'`,
         ].join('\n'),
         'Files written — install Claude Code to run the handoff',
       )
@@ -58,7 +58,7 @@ export const handoffClaudeStep: HandoffStep = {
     const exitCode = await spawnAgent('claude', launchPrompt)
     if (exitCode !== 0) {
       p.log.warn(
-        `Claude Code exited with code ${exitCode}. Re-run \`claude '${launchPrompt}'\` to resume.`,
+        `Claude Code exited with code ${exitCode}. Re-run \`claude --allow-dangerously-skip-permissions '${launchPrompt}'\` to resume.`,
       )
     }
 
diff --git a/packages/cli/src/commands/init/lib/handoff-helpers.ts b/packages/cli/src/commands/init/lib/handoff-helpers.ts
index 45b2e96e..bd4ac2d0 100644
--- a/packages/cli/src/commands/init/lib/handoff-helpers.ts
+++ b/packages/cli/src/commands/init/lib/handoff-helpers.ts
@@ -16,6 +16,11 @@ import {
  * prompt as a single argument. `stdio: 'inherit'` so the user sees tool
  * calls and approves edits live; the call resolves with the exit code.
  *
+ * Claude is launched with `--allow-dangerously-skip-permissions` so the
+ * user can opt in to skip-permissions mode for the integration handoff
+ * without having to relaunch — the flag permits the toggle, it doesn't
+ * force it on.
+ *
  * Returns -1 if the binary isn't on PATH (the spawn `error` event fires
  * before `close` does). Init never aborts on a non-zero code — the
  * artifacts are already written, the user can re-run the agent.
@@ -24,8 +29,12 @@ export function spawnAgent(
   binary: 'claude' | 'codex',
   prompt: string,
 ): Promise<number> {
+  const args =
+    binary === 'claude'
+      ? ['--allow-dangerously-skip-permissions', prompt]
+      : [prompt]
   return new Promise((resolvePromise) => {
-    const child = spawn(binary, [prompt], { stdio: 'inherit', shell: false })
+    const child = spawn(binary, args, { stdio: 'inherit', shell: false })
     child.on('close', (code) => resolvePromise(code ?? 0))
     child.on('error', () => resolvePromise(-1))
   })