What happened?
After working around the Cowork discovery problem reported in #61, I exported and privately synced a locally discoverable representation of a Claude Cowork session containing user attachments and files generated by Claude. The transcript was preserved, but the files were not.
Because the original cloud-backed session was not directly discoverable, the exact layer where the file bodies are lost may be Cowork ingestion, Simple export, or Skillsync sync. The observable problem is that the pipeline completes without preserving the files or warning that they were omitted.
The source session contains 39 visible file/artifact cards: XLSX, PDF, DOCX, JSON, Markdown, and a Claude artifact. The exported Simple document and the synced Skillsync session retain human-readable text such as [Shared files/artifacts: …], but do not contain downloadable file records or the underlying file bodies.
I expected the export described as the “full-fidelity Simple rendering” to preserve the files and their associations with the source messages. At minimum, if Cowork files are not supported, I expected an explicit warning listing the omitted files. Instead, the operation succeeds and produces a session that appears complete while silently omitting the primary work products.
For this session, I independently recovered 37 unique files. The 39 source cards reconcile to those 37 files, one duplicate appearance of an XLSX file, and one small Markdown file that was no longer available from Claude’s local cache.
How to reproduce
-
In Claude Desktop, create or open a Cowork session containing at least one uploaded file. Have Claude generate and return another file in the same session.
-
Confirm that both file cards are visible and downloadable in Claude.
-
Find the Cowork session:
-
Export it:
skl export <session-id> --from cowork --out session.simple.json
-
Inspect session.simple.json. The messages and display labels for shared files are present, but the original filenames, MIME types, message associations, and file bodies are not represented as downloadable attachments.
-
Sync the same session privately:
skl sync <session-id> --from cowork --private
-
Open the synced session in Skillsync. The transcript is present, but the uploaded and generated files cannot be downloaded.
This was confirmed with a real 173-message Cowork session containing 39 file/artifact cards. I can provide the private source session, exported Simple document, integrity hashes, and a redacted file bundle directly to the maintainers if useful; I have omitted those private identifiers and documents from this public report.
Versions
- txcript: 0.14.4 (embedded in
skl 0.35.4)
- Agents and their versions: Claude Desktop 2.7032.0; Skillsync CLI (
skl) 0.35.4
- Operating system: macOS 27.2 (Build 26B5091g)
What happened?
After working around the Cowork discovery problem reported in #61, I exported and privately synced a locally discoverable representation of a Claude Cowork session containing user attachments and files generated by Claude. The transcript was preserved, but the files were not.
Because the original cloud-backed session was not directly discoverable, the exact layer where the file bodies are lost may be Cowork ingestion, Simple export, or Skillsync sync. The observable problem is that the pipeline completes without preserving the files or warning that they were omitted.
The source session contains 39 visible file/artifact cards: XLSX, PDF, DOCX, JSON, Markdown, and a Claude artifact. The exported Simple document and the synced Skillsync session retain human-readable text such as
[Shared files/artifacts: …], but do not contain downloadable file records or the underlying file bodies.I expected the export described as the “full-fidelity Simple rendering” to preserve the files and their associations with the source messages. At minimum, if Cowork files are not supported, I expected an explicit warning listing the omitted files. Instead, the operation succeeds and produces a session that appears complete while silently omitting the primary work products.
For this session, I independently recovered 37 unique files. The 39 source cards reconcile to those 37 files, one duplicate appearance of an XLSX file, and one small Markdown file that was no longer available from Claude’s local cache.
How to reproduce
In Claude Desktop, create or open a Cowork session containing at least one uploaded file. Have Claude generate and return another file in the same session.
Confirm that both file cards are visible and downloadable in Claude.
Find the Cowork session:
skl list --from coworkExport it:
skl export <session-id> --from cowork --out session.simple.jsonInspect
session.simple.json. The messages and display labels for shared files are present, but the original filenames, MIME types, message associations, and file bodies are not represented as downloadable attachments.Sync the same session privately:
skl sync <session-id> --from cowork --privateOpen the synced session in Skillsync. The transcript is present, but the uploaded and generated files cannot be downloaded.
This was confirmed with a real 173-message Cowork session containing 39 file/artifact cards. I can provide the private source session, exported Simple document, integrity hashes, and a redacted file bundle directly to the maintainers if useful; I have omitted those private identifiers and documents from this public report.
Versions
skl0.35.4)skl) 0.35.4