macOS Apple Silicon: Python path not working despite correct configuration

[membranaestudio]

Environment

• OS: macOS Sequoia (Apple Silicon arm64)
• Auto Claude Version: Latest from releases
• Python Version: 3.12.12 (installed via Homebrew)
• Python Path: /opt/homebrew/bin/python3.12

Problem Description

After fresh installation of Auto Claude, multiple features fail with Python-related errors despite correctly configuring the Python path in Settings → Paths.

Errors Observed

1. Context Tab

Failed to load project index
spawn python ENOENT

2. Insights Tab (Chat)

Process exited with code 1

Attempting to chat results in immediate failure.

3. Roadmap Tab

Error
Generation failed
Roadmap generation failed with exit code 1

The process shows: Analyze → Discover → Generate, then fails.

4. Tasks

Tasks added to planning automatically move to "human review" and fail.

Steps Taken

1. Installed Auto Claude from DMG (arm64 version)
2. Encountered "spawn python ENOENT" error
3. Discovered system only had Python 3.9.6 (/usr/bin/python3)
4. Installed Python 3.12 via Homebrew: brew install python@3.12
5. Configured Python Path in Settings → Paths to /opt/homebrew/bin/python3.12
6. Saved settings and restarted Auto Claude
7. All errors persist unchanged

Expected Behavior

Features should work after configuring the correct Python 3.12 path.

Actual Behavior

All Python-dependent features continue to fail with the same errors.

Additional Context

This appears related to issues #402 and #454. The Python path configuration in Settings does not seem to be respected by the application.

Verification

Python is correctly installed and accessible:

$ /opt/homebrew/bin/python3.12 --version
Python 3.12.12

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[membranaestudio]

Additional Finding: Path Escaping Bug

After further investigation, we identified a path escaping bug in the application.

Error Message

[ERROR] spawn /Users/andrescerda/Library/Application ENOENT

Expected Path

/Users/andrescerda/Library/Application Support/auto-claude-ui/...

Root Cause

The path is being split at the space in "Application Support". The application is not properly escaping or quoting paths that contain spaces.

This affects:

• Roadmap generation
• Task execution
• Context/Project indexing

What We Tried (All Failed)

1. Installed Python 3.12 via Homebrew
2. Recreated the venv with Python 3.12 (this fixed Insights/Chat)
3. Configured Python Path in settings to various locations
4. Created symlink /usr/local/bin/python -> python3.12
5. Restarted Mac

Partial Success

After recreating the venv, Insights (chat) now works. But Roadmap, Context, and Tasks still fail due to the path escaping issue.

This appears to be a separate bug from the Python detection issue - it's a path handling bug on macOS where "Application Support" contains a space.

[Matrisis]

Hey i made a script to start auto-claude that fixes the issue :

set -euo pipefail

VENV_DIR="$HOME/.venvs/auto-claude"
VENV_PY="$VENV_DIR/bin/python"
SHIM_PATH="$HOME/Library/Application"
LOG_FILE="$HOME/.auto-claude-python-shim.log"

echo "==> Ensuring venv exists: $VENV_DIR"
if [ ! -x "$VENV_PY" ]; then
  /opt/homebrew/bin/python3 -m venv "$VENV_DIR"
fi

echo "==> Installing python-dotenv into venv"
"$VENV_PY" -m ensurepip --upgrade >/dev/null 2>&1 || true
"$VENV_PY" -m pip install --upgrade pip >/dev/null
"$VENV_PY" -m pip install -U python-dotenv >/dev/null

echo "==> Installing shim: $SHIM_PATH"
if [ -e "$SHIM_PATH" ] && [ ! -L "$SHIM_PATH" ]; then
  # Back up any existing file/dir named "Application" (rare)
  TS="$(date +%Y%m%d-%H%M%S)"
  mv "$SHIM_PATH" "${SHIM_PATH}.bak.${TS}"
fi

cat > "$SHIM_PATH" <<'EOF'
#!/usr/bin/env bash
set -euo pipefail

VENV_PY="$HOME/.venvs/auto-claude/bin/python"
LOG_FILE="$HOME/.auto-claude-python-shim.log"

# Auto-Claude bug: tries to spawn "/Users/.../Library/Application Support/...."
# but passes it unescaped so we get called as:
#   ~/Library/Application  Support/....
#
# Rebuild the intended absolute path:
if [ "${1:-}" = "" ]; then
  echo "[$(date -Iseconds)] shim invoked with no args" >> "$LOG_FILE"
  exit 127
fi

TARGET="$HOME/Library/Application $1"
shift || true

{
  echo "[$(date -Iseconds)] shim invoked"
  echo "  TARGET=$TARGET"
  echo "  ARGS=$*"
} >> "$LOG_FILE"

# If TARGET looks like a python script, run it with the venv python.
if [[ "$TARGET" == *.py ]]; then
  exec "$VENV_PY" "$TARGET" "$@"
fi

# If it’s an executable file, run it.
if [ -x "$TARGET" ]; then
  exec "$TARGET" "$@"
fi

# Fallback: try running TARGET as an argument to python (helps debugging).
exec "$VENV_PY" "$TARGET" "$@"
EOF

chmod +x "$SHIM_PATH"

echo "==> Launching Auto-Claude"
open -a "Auto-Claude"

echo "==> Done."
echo "If it still errors, check logs: $LOG_FILE"

[membranaestudio]

It works! Confirmed on macOS Sequoia (Apple Silicon).

I made a minor change, using /opt/homebrew/bin/python3.12 instead of python3 to specify the exact version.

After applying the shim, Context, Roadmap and Tasks work correctly.

Thanks Matrisis

[akmittal006]

the above srcipt isn'w working for me.
seeing

Failed to load project index

Analyzer exited with code 1

[joelfuller2016]

@openhands-agent Please fix this macOS Python path configuration bug.

Issue Summary: Python path configured in Settings → Paths is ignored. All Python-dependent features fail with "spawn python ENOENT" despite correct configuration.

Platform: macOS Sequoia (Apple Silicon arm64)
Python: 3.12.12 via Homebrew at /opt/homebrew/bin/python3.12

Failing Features:

• Context Tab: "Failed to load project index - spawn python ENOENT"
• Insights Tab: "Process exited with code 1"
• Roadmap Tab: "Roadmap generation failed with exit code 1"
• Tasks: Immediately move to "human review" and fail

Related Issues: #402, #454, #474

Investigation Areas:

1. apps/frontend/src/main/index.js - Check parsePythonCommand() function
2. Check how pythonPath setting is loaded and passed to subprocess calls
3. Verify spawn command construction for macOS paths

Root Cause: The pythonPath setting from Settings is not being respected when spawning Python processes. The app likely uses hardcoded "python" or ignores the configured path.

Required Fix:

1. Ensure pythonPath from settings is loaded correctly
2. Pass the full configured path to all subprocess.spawn calls
3. Handle macOS Homebrew paths (which contain /opt/homebrew/)
4. Add validation to confirm the configured path is used

Target Branch: develop

[AndyMik90]

✅ This issue has been fixed

This issue was resolved by commit 8d58dd6f - fix: prefer versioned Homebrew Python over system python3 (#494)

What was fixed:

• Added multi-version Homebrew Python detection in cli-tool-manager.ts (lines 216-322)
• The detectPython() method now has a multi-level priority system:
  1. Configured path (if valid)
  2. Versioned Homebrew Python (python3.14, 3.13, 3.12, 3.11, 3.10)
  3. Generic Homebrew python3
  4. System python3
• Properly supports Apple Silicon Macs with /opt/homebrew/bin paths
• Validates each Python version to ensure 3.10+ requirement

How to get the fix:

Please update to Auto-Claude v2.7.2 or later to get this fix.

Related issues:

• No task is running #567 (No task is running - dotenv) - Same root cause ✅ Fixed
• Auto Claude does not detect Homebrew Python (3.14) on macOS and fails with EACCES when custom path is provided #402 (Does not detect Homebrew Python 3.14) - Same root cause

If you're still experiencing this issue after updating to v2.7.2+, please let us know and we'll reopen this issue.

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