Desktop app: Bypass Permissions mode flips to Accept Edits on first prompt (M5 / macOS 26.5)

Summary

On Claude Desktop 2.1.149, every new session correctly starts in Bypass Permissions mode (yellow chip), but the instant the first prompt is sent the mode flips to Accept Edits. The flip is deterministic, immediate, and reproduces with both slash commands and plain text. Every settings-level fix is in place; the bug appears to be in the app itself.

Environment

• App: Claude Desktop (entrypoint claude-desktop)
• Version: 2.1.149
• OS: macOS 26.5 (build 25F71)
• Hardware: MacBook Air M5, 24 GB RAM (Mac17,4)
• Plan: Max
• Same user account works correctly on a different (older) Mac — issue is specific to this machine. Could be related to macOS 26.5 or M5 chip newness.

Reproduction

1. Launch Claude Desktop, open any project.
2. Start a new session — chip at bottom-left correctly reads "Bypass permissions" (yellow).
3. Send any prompt (tested with /session-restart and plain hello).
4. The instant the prompt is submitted, chip flips to "Accept edits".
5. Toast appears: "Bypass Permissions mode isn't enabled. The session started in Accept Edits — enable Bypass Permissions in Settings to use it."
6. Clicking the chip to switch back fails with: "Permission mode couldn't be changed. You can try again."

What's Configured Correctly

• ~/.claude/settings.json → permissions.defaultMode: "bypassPermissions" ✓
• .claude/settings.local.json (project) → permissions.defaultMode: "bypassPermissions" ✓
• In-app Settings → Claude Code → "Allow bypass permissions mode" toggle → ON ✓
• skipDangerousModePermissionPrompt: true ✓
• No managed/policy settings (/Library/Application Support/ClaudeCode/, /etc/claude-code/ empty)
• No UserPromptSubmit / SessionStart hooks anywhere
• No plugins enabled (enabledPlugins absent in all settings files)

What Was Tried (all unsuccessful)

1. Patching permissions.defaultMode at user level.
2. Patching permissions.defaultMode at project-local level.
3. Cmd+Q fully quit and relaunch — 6+ times.
4. Disabling "Enable remote control by default" (also tested ON).
5. Plain text prompt vs slash command — both flip identically.
6. Full computer restart.

Related

• #29026 — Desktop app ignores settings.json defaultMode (similar but distinct: that issue is "ignored at startup," this is "flipped after startup on first prompt").
• #37029 — Bypass permissions mode still prompts for settings.json edits.

Severity

High for Max users on new Apple Silicon Macs. Bypass mode is a paid-tier productivity feature with no user-accessible workaround when the flip occurs.