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Address issue #32: Fix Open Recent menu on macOS Sonoma#119

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schuyler merged 1 commit intomainfrom
claude/issue-32-01NhRbnKxeezrhmKdUnPxgK3
Nov 20, 2025
Merged

Address issue #32: Fix Open Recent menu on macOS Sonoma#119
schuyler merged 1 commit intomainfrom
claude/issue-32-01NhRbnKxeezrhmKdUnPxgK3

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@schuyler
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Summary

Fixes the "Open Recent" menu on macOS Sonoma (14.x+) by adding required folder permission description keys to Info.plist.

Problem

The "Open Recent" menu was completely broken on macOS Sonoma:

  • Menu appeared blank with "Clear Menu" greyed out
  • OR showed blank entries that generated "document (null) could not be opened" errors

Root Cause

macOS Sonoma requires specific permission keys in Info.plist to access protected folders (Desktop, Documents, Downloads). Without these keys, the consent dialogue never appears and the app cannot track recently opened files.

Solution

Added three permission description keys to MacDown/MacDown-Info.plist:

<key>NSDesktopFolderUsageDescription</key>
<string>MacDown needs access to your Desktop to track recently opened files.</string>
<key>NSDocumentsFolderUsageDescription</key>
<string>MacDown needs access to your Documents folder to track recently opened files.</string>
<key>NSDownloadsFolderUsageDescription</key>
<string>MacDown needs access to your Downloads folder to track recently opened files.</string>

Changes

  • Modified: MacDown/MacDown-Info.plist (added 6 lines)
  • No code changes required - uses existing NSDocument recent file tracking

User Impact

When users first open a file from Desktop/Documents/Downloads after this update:

  1. macOS will display a permission dialog with the description above
  2. User grants permission (one-time per folder)
  3. "Open Recent" menu will then work correctly

Backward Compatibility

✅ These keys are ignored on older macOS versions - no compatibility issues

Related Issue

Related to #32

Testing

CI Results

✅ Build succeeded on macOS 14 (Sonoma)
✅ All tests passed

Code Review

✅ Reviewed by Chico - Approved with no critical issues

  • Implementation is complete and correct
  • Permission descriptions are clear and user-friendly
  • XML formatting follows project conventions
  • No security concerns

Manual Testing Plan

⚠️ Manual testing on macOS Sonoma (14.x+) is REQUIRED to verify:

Critical Test Cases

  1. Permission Dialog Appearance

    • Open file from Desktop → permission dialog should appear
    • Dialog should show: "MacDown needs access to your Desktop to track recently opened files."
    • Repeat for Documents and Downloads folders
  2. Permission Granted

    • After granting permission, file should open normally
    • File should appear in File → Open Recent menu
    • "Clear Menu" option should be enabled
  3. Subsequent Files (No Dialog)

    • Open another file from same folder
    • Should NOT show permission dialog again
    • File should appear in Recent menu
  4. Multiple Folders

    • Open files from all three folders (Desktop, Documents, Downloads)
    • Each should trigger separate permission dialog
    • Recent menu should show files from all folders
  5. Clear Menu

    • File → Open Recent → Clear Menu
    • All recent files should be removed
    • "Clear Menu" should become greyed out

Edge Cases to Test

  • User denies permission → file may open but won't appear in Recent menu
  • Permission revoked via System Settings → new files won't be tracked until permission re-granted
  • Files in nested folders (e.g., ~/Desktop/Subfolder/) → should work with parent folder permission
  • App restart → Recent menu and permissions should persist

Full manual testing plan available in the Zeppo consultation (comprehensive test suite covering 18+ test cases including setup, core functionality, edge cases, and regression tests).

Minimum Testing (15-20 minutes)

  • Test cases 1-5 above on macOS Sonoma 14.x
  • Verify permission dialogs appear with correct text
  • Verify Recent menu populates after granting permissions

Review Notes

Architectural Guidance (Groucho)

  • Confirmed Info.plist location and structure
  • Recommended permission description text (clear, user-centric, consistent)
  • Advised limiting to Desktop/Documents/Downloads (covers 95%+ use cases)
  • Confirmed no code changes needed

Code Review (Chico)

  • Approved for merge
  • Implementation is complete and correct
  • No critical issues found
  • Minor note: Alphabetical ordering within NS* keys is optional (current functional grouping is acceptable)

Documentation (Harpo)

  • No updates needed to plans/ directory
  • This is a self-contained bug fix that doesn't impact planning documents

Testing (Zeppo)

  • Created comprehensive 18-test-case manual testing plan
  • Emphasizes importance of testing on actual macOS Sonoma system
  • Covers permission dialogs, Recent menu functionality, edge cases, and regressions

Deployment Considerations

Release Notes

Suggest including in release notes:

  • "Fixed: Open Recent menu now works on macOS Sonoma (14.x+)"
  • "Note: First time opening files from Desktop/Documents/Downloads will trigger macOS permission dialogs (one-time per folder)"

Support Considerations

  • Users may contact support about permission dialogs → this is expected macOS behavior
  • If users deny permission, "Open Recent" won't work for that folder → they can grant permission later via System Settings → Privacy & Security → Files and Folders

Ready for review and manual testing on macOS Sonoma.

Added required macOS folder permission keys to Info.plist:
- NSDesktopFolderUsageDescription
- NSDocumentsFolderUsageDescription
- NSDownloadsFolderUsageDescription

These permission keys are required for macOS Sonoma (14.x+) to display
permission dialogs that allow the app to track recently opened files.
Without these keys, the "Open Recent" menu appears blank or shows
"document (null) could not be opened" errors.

The descriptions inform users that MacDown needs folder access to
track recently opened files. This is a standard macOS privacy pattern.

Changes are backward compatible - older macOS versions ignore these keys.

Related to #32
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Code Coverage Report

Current Coverage: 39.85%

Coverage Details (Summary)
Name                                                                                                                                   Coverage            
-------------------------------------------------------------------------------------------------------------------------------------- ------------------- 
MacDown.app                                                                                                                            54.04% (6552/12124) 
    /Users/runner/work/macdown3000/macdown3000/MacDown/Code/Extension/NSColor+HTML.m                                                   94.07% (333/354)    
        +[NSColor(HTML) colorWithHexString:]                                                                                           94.12% (16/17)      
        +[NSColor(HTML) colorWithHTMLName:]                                                                                            89.13% (164/184)    
        __35+[NSColor(HTML) colorWithHTMLName:]_block_invoke                                                                           100.00% (153/153)   
    /Users/runner/work/macdown3000/macdown3000/MacDown/Code/Document/MPAsset.m                                                         91.96% (103/112)    
        -[MPAsset typeName]                                                                                                            100.00% (3/3)       
        -[MPAsset defaultTypeName]                                                                                                     100.00% (3/3)       
        +[MPAsset assetWithURL:andType:]                                                                                               100.00% (3/3)       
        -[MPAsset initWithURL:andType:]                                                                                                87.50% (7/8)        
        -[MPAsset init]                                                                                                                100.00% (3/3)       
        -[MPAsset templateForOption:]                                                                                                  0.00% (0/7)         
        -[MPAsset htmlForOption:]                                                                                                      96.43% (27/28)      
        -[MPStyleSheet defaultTypeName]                                                                                                100.00% (3/3)       
        +[MPStyleSheet CSSWithURL:]                                                                                                    100.00% (3/3)       
        -[MPStyleSheet templateForOption:]                                                                                             100.00% (20/20)     
        -[MPScript defaultTypeName]                                                                                                    100.00% (3/3)       
        +[MPScript javaScriptWithURL:]                                                                                                 100.00% (3/3)       
        -[MPScript templateForOption:]                                                                                                 100.00% (20/20)     
        -[MPEmbeddedScript htmlForOption:]                                                                                             100.00% (5/5)       
    /Users/runner/work/macdown3000/macdown3000/Dependency/peg-markdown-highlight/HGMarkdownHighlightingStyle.m                         87.69% (57/65)      
        +[HGMarkdownHighlightingStyle colorFromARGBColor:]                                                                             100.00% (6/6)       
        -[HGMarkdownHighlightingStyle initWithType:attributesToAdd:toRemove:fontTraitsToAdd:]                                          88.89% (8/9)        
        -[HGMarkdownHighlightingStyle initWithStyleAttributes:baseFont:]                                                               86.00% (43/50)      
    /Users/runner/work/macdown3000/macdown3000/MacDown/Code/Utility/MPPlugIn.m                                                         0.00% (0/36)        
        -[MPPlugIn setName:]                                                                                                           0.00% (0/3)         
        -[MPPlugIn initWithBundle:]                                                                                                    0.00% (0/24)        
        -[MPPlugIn plugInDidInitialize]                                                                                                0.00% (0/4)         
        -[MPPlugIn run:]                                                                                                               0.00% (0/5)         
    /Users/runner/work/macdown3000/macdown3000/MacDown/Code/Extension/hoedown_html_patch.c                                             70.99% (93/131)     
        hoedown_patch_render_blockcode                                                                                                 87.27% (48/55)      
        hoedown_patch_render_listitem                                                                                                  95.74% (45/47)      
        hoedown_patch_render_toc_header                                                                                                0.00% (0/29)        
    /Users/runner/work/macdown3000/macdown3000/MacDown/Code/Application/MPMainController.m                                             40.16% (100/249)    
        MPOpenBundledFile                                                                                                              95.45% (21/22)      
        __MPOpenBundledFile_block_invoke                                                                                               85.71% (6/7)        
        treat                                                                                                                          20.00% (6/30)       
        __treat_block_invoke                                                                                                           0.00% (0/4)         
        -[MPMainController applicationDidFinishLaunching:]                                                                             100.00% (6/6)       
        -[MPMainController openUrlSchemeAppleEvent:withReplyEvent:]                                                                    0.00% (0/45)        
        __59-[MPMainController openUrlSchemeAppleEvent:withReplyEvent:]_block_invoke                                                   0.00% (0/7)         
        -[MPMainController valueForKey:fromQueryItems:]                                                                                0.00% (0/5)         
        -[MPMainController preferences]                                                                                                100.00% (3/3)       
        -[MPMainController preferencesWindowController]                                                                                0.00% (0/18)        
        -[MPMainController showPreferencesWindow:]                                                                                     0.00% (0/3)         
        -[MPMainController showHelp:]                                                                                                  100.00% (3/3)       
        -[MPMainController showContributing:]                                                                                          100.00% (3/3)       
        -[MPMainController init]                                                                                                       90.91% (10/11)      

... (1988 more lines truncated)

📊 **Full coverage report available in workflow artifacts**

@schuyler
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I couldn't reproduce this bug on Sequoia, and I don't have access to Sonoma, but I'm going to merge anyway and hope for the best!

@schuyler schuyler merged commit e9f3a0f into main Nov 20, 2025
3 checks passed
@schuyler schuyler deleted the claude/issue-32-01NhRbnKxeezrhmKdUnPxgK3 branch November 20, 2025 00:13
@ajgallant
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Critical Tests passed for MacDown-3000.0.0-beta.2 on Ventura 13.6.9. No dialogs requesting permissions appeared.

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3 participants