The Set Up button in the iloom extension in VSCode shoudl disappear once setup has been completed

[Gromski]

Diagnostic Information

Property	Value
CLI Version	0.5.3
Node.js Version	v24.5.0
OS	darwin
OS Version	25.1.0
Architecture	x64
Capabilities	web
Claude CLI Version	2.0.73 (Claude Code)

The Set Up button in the iloom extension in VSCode shoudl disappear once setup has been completed

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Enhancement Request Analysis

Questions for Reporter

Question	Answer
Which version of the iloom VSCode extension are you using?	@Gromski, please edit this issue to answer these questions.
Does the Set Up button remain visible after successfully running il init or after creating your first loom with il start?
Are you seeing any error messages in the VSCode extension output panel or developer console when attempting to complete setup?
What specific setup steps have you completed (e.g., GitHub authentication, Claude CLI authentication, project configuration)?

Problem Summary
The Set Up button in the iloom VSCode extension continues to display even after the user has completed the iloom CLI setup process, creating confusion about whether configuration is complete and potentially leading users to unnecessarily repeat setup steps.

User Impact
Users of the iloom VSCode extension experience uncertainty about their setup status and may waste time re-running configuration steps. This affects developers who rely on the visual indicator to understand if their iloom environment is properly configured for use with Claude Code integration.

Enhancement Goal
The Set Up button should automatically hide or change state once iloom CLI setup is complete, providing clear visual feedback that the extension is ready to use. The extension should detect completion of setup through checking for presence of .iloom/settings.json, successful authentication with required services (GitHub, Claude), and potentially a setup completion flag.

Next Steps

• Reporter to answer questions above for full context
• Investigate how the VSCode extension currently determines setup status
• Define criteria for "setup complete" state (presence of config files, authentication status, etc.)
• Implement state detection mechanism in the extension to hide/update the Set Up button

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📋 Complete Context & Details (click to expand)

Current Behavior
The iloom VSCode extension displays a Set Up button that persists even after users have completed the iloom CLI configuration process. Based on the codebase analysis, the extension integrates with iloom CLI through Unix socket communication and Claude Code hooks (via templates/hooks/iloom-hook.js and ClaudeHookManager), enabling real-time monitoring of Claude session state. The extension also supports workspace color synchronization through the VSCodeIntegration class.

Proposed Solution
The VSCode extension should detect setup completion by checking for:

1. Presence of iloom configuration files (.iloom/settings.json or .iloom/settings.local.json)
2. Authentication status with required services:
   • GitHub CLI authentication (gh auth status)
   • Claude CLI authentication (checking if claude command is available)
   • Optional: Neon CLI authentication if database features are configured
3. A setup completion flag that could be set in the settings file after successful il init execution

The extension could implement a status check that:

• Runs on extension activation
• Periodically polls for setup status changes
• Listens for file system changes to .iloom/ directory
• Receives setup completion signals via the existing Unix socket communication mechanism

Benefits

• Reduces user confusion about setup status
• Prevents unnecessary repetition of setup steps
• Provides clear visual feedback about extension readiness
• Improves the onboarding experience for new iloom users
• Aligns with the iloom philosophy of maintaining clear context and reducing friction in AI-assisted development

[acreeger]

Just filed the exact same bug in the VScode repo - will work on this now

[acreeger]

Analysis: Project Marker File Creation

I investigated the codepath for how iloom tracks configured projects. This is directly relevant to determining setup completion status.

Current Behavior

Projects are tracked via marker files in ~/.config/iloom-ai/projects/<encoded-path>. These markers are created by FirstRunManager.markProjectAsConfigured().

Entry Point	Creates Marker?
il start/enhance/add-issue → launchFirstRunSetup() → InitCommand.execute()	✅ Yes
il init directly	❌ No

The Problem

When a user runs il init directly:

1. .iloom/ directory is created, .gitignore updated
2. Claude configuration session runs
3. But no global marker is created

This means:

• The project won't appear in il projects list
• needsFirstRunSetup() may still trigger the wizard on subsequent commands
• The VSCode extension has no reliable way to detect that setup completed

Recommendation

InitCommand.execute() should call markProjectAsConfigured() at the end when it completes successfully. This would:

1. Enable VSCode extension detection - The extension can watch/check for ~/.config/iloom-ai/projects/* marker files to determine setup status
2. Consistency - Direct il init and first-run wizard would behave identically
3. Projects list - Project shows in il projects immediately after init

Implementation

Add to end of InitCommand.execute() (around line 49 in src/commands/init.ts):

// Mark project as configured
const { getRepoRoot } = await import('../utils/git.js')
const { FirstRunManager } = await import('../utils/FirstRunManager.js')
const projectRoot = await getRepoRoot() ?? process.cwd()
const firstRunManager = new FirstRunManager()
await firstRunManager.markProjectAsConfigured(projectRoot)

This gives the VSCode extension a reliable signal to check for setup completion.

[acreeger]

Complexity Assessment

Classification: TRIVIAL

Metrics:

• Estimated files affected: 1
• Estimated lines of code: 10-15
• Breaking changes: No
• Database migrations: No
• Cross-cutting changes: No
• File architecture quality: Good (489 LOC file, well-structured)
• Overall risk level: Low

Reasoning: This is a simple, targeted fix requiring a single method call added to InitCommand.execute() at end of file. The markProjectAsConfigured() method already exists, is defensive (non-throwing on errors), and matches existing patterns used in the codebase. No architectural complexity, breaking changes, or cross-cutting dependencies.

[acreeger]

Implementation Complete - Issue #397

Summary

Added markProjectAsConfigured() call at the end of InitCommand.execute() so that running il init directly now creates the global project marker file, enabling the VSCode extension to detect setup completion.

Changes Made

• src/commands/init.ts: Added call to FirstRunManager.markProjectAsConfigured() after guided init completes

Validation Results

• Tests: 3066 passed / 3066 total (23 skipped)
• Typecheck: Passed (via build)
• Lint: Passed (via build)

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Detailed Changes by File (click to expand)

Files Modified

src/commands/init.ts

Changes: Added markProjectAsConfigured() call after launchGuidedInit() completes (lines 50-57)

• Uses dynamic imports following existing codebase patterns
• Gets project root via getRepoRoot() with fallback to process.cwd()
• Creates FirstRunManager instance and calls markProjectAsConfigured()
• Includes debug logging for troubleshooting

Files Created

None

Test Coverage Added

Existing tests cover FirstRunManager.markProjectAsConfigured() behavior - no new tests needed for this integration.

Dependencies Added

None

[acreeger]

iloom Session Summary

Key Themes:

• Fixed issue where il init wasn't marking projects as configured, preventing VSCode extension detection
• Avoided dynamic imports per project guidelines; used static imports with proper error handling
• Made markProjectAsConfigured() idempotent with defense-in-depth checking at both call site and method level

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Session Details (click to expand)

Key Insights

• The project marker file in ~/.config/iloom-ai/projects/<encoded-path> is the mechanism VSCode extension uses to detect setup completion
• getRepoRoot() returns null in non-git directories (expected behavior), falling back to process.cwd()
• launchClaude() throws on failure in interactive mode, so catching errors in launchGuidedInit() is necessary to prevent crashes
• The "not a git repository" error is a normal case when running il init outside git repos, not a warning condition

Decisions Made

• Made launchGuidedInit() return boolean: Returns true on success, false on failure. This allows InitCommand.execute() to only mark project as configured when Claude session actually completes successfully, not when it fails or is unavailable
• Defense-in-depth idempotency: Added checks at both layers - InitCommand.execute() checks before calling, and markProjectAsConfigured() checks internally. Prevents duplicate marker writes when running il init multiple times or when il start triggers first-run setup
• Downgraded "not a git repository" log level: Changed from warn to info because this is expected behavior in non-git directories, not an error condition

Challenges Resolved

• Dynamic import violation: Initial implementation used await import() for getRepoRoot and FirstRunManager. Fixed by adding static imports at file top per project anti-pattern guidelines
• Duplicate marking in first-run-setup: launchFirstRunSetup() was calling markProjectAsConfigured() after initCommand.execute(), but we moved that logic into InitCommand itself. Removed duplicate call and updated tests to verify delegation pattern
• Non-git directory warnings: Users saw confusing warnings when running il init outside git repos. Added check in getRepoRoot() error handler to distinguish expected "not a git repository" errors from actual failures

Lessons Learned

• FirstRunManager.markProjectAsConfigured() is defensive - catches all errors and logs them without throwing, so it's safe to call even if filesystem operations fail
• The fallback pattern await getRepoRoot() ?? process.cwd() is used throughout the codebase for consistent project path resolution whether in git repos or standalone directories
• Test mocks for InitCommand were expecting direct calls to markProjectAsConfigured(), but after moving the logic into the command itself, tests needed updating to verify delegation pattern instead

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