I use DTPro with To Go my iPhones and iPad and synced to my Macbook. Not updated Mac OS to Catalina but otherwise everything is up to date.
I receive a constant Connection to server timed out. I left my home with my iPad to be attached to my iMac with a Lightning cable to sync, and spent like 8 hours outside. When I returned home I had the error message like 60 times - like this
|19:24:44: email@example.com|Connection to server timed out.|
|19:31:09: firstname.lastname@example.org|Connection to server timed out.|
|19:38:08: email@example.com|Connection to server timed out.|
I do not think that when the two devices are connected with a direct cable I need t restart my router or my computer as I thought that the sync connects the two devices quite directly.
This error message came out many times in the last 2-3 weeks and I had never such a problem when I sync my iMac with my Macbook.
Have no idea what to do but it is very time-consuming and a sync should be working perfectly.