Sync error after uploading file to rM

[abmantis]

If I use the put command to send a PDF to the rM, the file is downloaded on the rM, I see the cloud icon on the file blink 3 times, and I get a "Not able to upload file" error and then the "Sync failed" bar.

After taking a look at the journal, I see the following:

Feb 17 00:38:01 reMarkable xochitl[3616]: 00:38:01.674 rm.network.document.uploaderContent not modified, but uploading anyway just to be sure
Feb 17 00:38:01 reMarkable xochitl[3616]: 00:38:01.955 rm.network.document.uploaderDocument upload url failed for version: "8de92d3c-5dc4-45d8-9ed6-3dea3635dc7f" 1
Feb 17 00:38:01 reMarkable xochitl[3616]: 00:38:01.956 rm.network.document.uploaderNo valid upload URLs were received for file: "8de92d3c-5dc4-45d8-9ed6-3dea3635dc7f" 1
Feb 17 00:38:02 reMarkable xochitl[3616]: 00:38:02.914 rm.network.document.uploaderContent not modified, but uploading anyway just to be sure
Feb 17 00:38:03 reMarkable xochitl[3616]: 00:38:03.010 rm.network.document.uploaderDocument upload url failed for version: "8de92d3c-5dc4-45d8-9ed6-3dea3635dc7f" 1
Feb 17 00:38:03 reMarkable xochitl[3616]: 00:38:03.010 rm.network.document.uploaderNo valid upload URLs were received for file: "8de92d3c-5dc4-45d8-9ed6-3dea3635dc7f" 1
Feb 17 00:38:03 reMarkable xochitl[3616]: 00:38:03.968 rm.network.document.uploaderContent not modified, but uploading anyway just to be sure
Feb 17 00:38:04 reMarkable xochitl[3616]: 00:38:04.074 rm.network.document.uploaderDocument upload url failed for version: "8de92d3c-5dc4-45d8-9ed6-3dea3635dc7f" 1
Feb 17 00:38:04 reMarkable xochitl[3616]: 00:38:04.074 rm.network.document.uploaderNo valid upload URLs were received for file: "8de92d3c-5dc4-45d8-9ed6-3dea3635dc7f" 1
Feb 17 00:38:04 reMarkable xochitl[3616]: 00:38:04.078 rm.network.document.uploaderUpload task was rejected from the queue "8de92d3c-5dc4-45d8-9ed6-3dea3635dc7f" 3

I also get a sync error on that file if I open the Android app.
If I edit the file, it syncs fine from that point on.