You can automatically delete files based on certain criteria with Syncovery. A frequently requested functionality is to delete files from a folder which are older than X days.
To delete files, you need to set up a job (profile) and mirror an empty folder to the destination using Exact Mirror Mode. For example, you can use a File Age filter to delete files older than 14 days only. You need to use Advanced Mode in Syncovery to do this.
After setting the job up with the correct filters, you need to test it in Attended Mode. Run the job manually and look at the Sync Preview to make sure it works correctly and deletes the correct files only. Then you can give it a schedule.
If you have thoroughly verified that the profile works 100% correctly, and does not delete any files that you want to keep, then go to Safety->Unattended and allow 100% deletions (because 100% of the older files are deleted).
To enable these deletions to occur in unattended mode, you also need to add a switch to the INI file. Add the following line to the [Main] section of the Syncovery.ini file (on Windows) in order to enable 100% deletions: