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  • I don’t believe the backup job actually “overwrites” the Dropbox content. Here’s what I see in my backup log:

    [03-Jan-2017 03:11:23] 1. Try to send backup file to Dropbox …
    [03-Jan-2017 03:11:39] Authenticated with Dropbox of user: username
    [03-Jan-2017 03:11:39] Uploading to Dropbox …
    [03-Jan-2017 03:12:05] Backup transferred to https://content.dropboxapi.com/1/files/sandbox/Backups/my-test-backwpup_e019a0_2017-01-02_19-10-57.tar.gz
    [03-Jan-2017 03:12:35] One file deleted from Dropbox

    This would seem to indicate that the backup job needs enough room to write the current backup file. When that completes the job checks the option “File Deletion” number. If that has been exceeded then the job will delete the oldest backup from Dropbox. If there isn’t enough room for the current backup to complete successfully then you get the message you’re currently seeing.

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