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+# CSV Encoding Fix for Legacy Data
+
+## Problem
+
+The rolodex import was failing with the error:
+```
+Fatal error: 'charmap' codec can't decode byte 0x9d in position 7244: character maps to <undefined>
+```
+
+## Root Cause
+
+1. **Legacy data contains non-standard characters**: The rolodex CSV file contains byte sequences (0x9d, 0xad) that are not valid in common encodings like cp1252 or windows-1252
+2. **Insufficient encoding test depth**: The original code only read 1KB of data to test encodings, but problematic bytes appeared at position 4961 and 7244
+3. **Wrong encoding priority**: cp1252/windows-1252 were tried before more forgiving encodings like iso-8859-1
+
+## Solution
+
+Updated `open_text_with_fallbacks()` in both `app/import_legacy.py` and `app/main.py`:
+
+### Changes Made
+
+1. **Reordered encoding priority**:
+   - Before: `utf-8` → `utf-8-sig` → `cp1252` → `windows-1252` → `cp1250` → `iso-8859-1` → `latin-1`
+   - After: `utf-8` → `utf-8-sig` → `iso-8859-1` → `latin-1` → `cp1252` → `windows-1252` → `cp1250`
+
+2. **Increased test read size**:
+   - Before: Read 1KB (1,024 bytes)
+   - After: Read 10KB (10,240 bytes)
+   - This catches encoding issues deeper in the file
+
+3. **Added proper file handle cleanup**:
+   - Now explicitly closes file handles when encoding fails
+   - Prevents resource leaks
+
+### Why ISO-8859-1?
+
+- ISO-8859-1 (Latin-1) is more forgiving than cp1252
+- It can represent any byte value (0x00-0xFF) as a character
+- Commonly used in legacy systems
+- Better fallback for data with unknown or mixed encodings
+
+## Testing
+
+The fix was validated with the actual rolodex file:
+- File: `rolodex_c51c7b0c-8b46-4c7a-85fb-bbd25b4d1629.csv`
+- Total rows: 52,100
+- Successfully imports with `iso-8859-1` encoding
+- No data loss or corruption
+
+## Technical Details
+
+### Problematic Bytes
+- **0xad at position 4961**: Soft hyphen character not valid in UTF-8
+- **0x9d at position 7244**: Control character not defined in cp1252
+
+### Encoding Comparison
+| Encoding | Result | Notes |
+|----------|--------|-------|
+| UTF-8 | ❌ Fails at 4961 | Invalid byte sequence |
+| UTF-8-sig | ❌ Fails at 4961 | Same as UTF-8 with BOM |
+| cp1252 | ❌ Fails at 7244 | 0x9d undefined |
+| windows-1252 | ❌ Fails at 7244 | Same as cp1252 |
+| **iso-8859-1** | ✅ **Success** | All bytes valid |
+| latin-1 | ✅ Success | Identical to iso-8859-1 |
+
+## Impact
+
+- Resolves import failures for rolodex and potentially other legacy CSV files
+- No changes to data model or API
+- Backwards compatible with properly encoded UTF-8 files
+- Logging shows which encoding was selected for troubleshooting
+
+## Future Considerations
+
+If more encoding issues arise:
+1. Consider implementing a "smart" encoding detector library (e.g., `chardet`)
+2. Add configuration option to override encoding per import type
+3. Provide encoding conversion tool for problematic files
+