Claude Desktop does not display earlier session history for long conversations after multiple compacts

Description

In Claude Desktop, conversation history from earlier sessions is not displayed in any view mode for long conversations that have been compacted multiple times. The full data is preserved in local .jsonl files but is completely inaccessible through the Desktop UI.

Environment

• Platform: Windows 11 (both machines)
• Claude Desktop version: 1.11187.4.0
• Claude Code CLI version: 2.1.159

Reproduction

I have a project with a long conversation spanning 9 separate sessions (via claude --resume), with multiple compacts performed throughout. The latest session shows:

• 18 turns, 175 tool calls, 20h 3m, 166.0k tokens
• Only 18 turns are visible in any Desktop view mode
• All conversation history from earlier sessions (hundreds of turns) is missing from the UI
• The data can be verified by reading the local .jsonl files under ~/.claude/projects/

Key observations

1. Local data is intact: All session .jsonl files are fully preserved under ~/.claude/projects/. File sizes range from 61K to 3.6M, totaling the complete conversation history.

1. claude --resume works correctly: Resuming any of the 9 sessions via CLI shows the full transcript for that session.

1. Another computer does not exhibit this behavior: A different Windows 11 machine with the exact same Claude Desktop version displays conversation history correctly. The difference is that the other machine's conversations are shorter.

1. Previously visible, now gone: Earlier compacts in this conversation preserved the history visibility in the UI. The disappearance happened after the conversation grew very large (166k+ tokens).

1. No configuration differences: Both machines have identical config.json, claude_desktop_config.json, and developer_settings.json.

Expected behavior

Claude Desktop should display conversation history from earlier sessions in the UI, allowing users to review the full conversation without needing to read raw .jsonl files.

Actual behavior

Only 18 turns (from the most recent session) are visible in Claude Desktop. All earlier session history is inaccessible from the UI. The only way to access it is by reading local .jsonl files directly.

Workaround

Reading session .jsonl files from ~/.claude/projects/ or using claude --resume <session-id> in the CLI.