Connection to server timed out

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: mobile@ipad-80.local|Connection to server timed out.|
|19:31:09: mobile@ipad-80.local|Connection to server timed out.|
|19:38:08: mobile@ipad-80.local|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.

Did you enable incoming Bonjour connections on both devices? This is usually not necessary and not recommended and cause such issues. It’s sufficient to enable them on the Mac and to add a Bonjour sync location on iOS.

Bonjour was on for my iMac but off for my iPad. I witched off Bonjour on my iMac and now my local network offline meaning no sync…

Are the databases on the iPad up-to-date? A timeout is not necessarily a real issue as the next sync will resume the previous one.

I guess they are not as I divided my previous database into two small ones, had the same problems and I deleted one of the databases from my iPad and then I tried to sync the new database. You wrote that a timeout is not an issue but it stops the procedure, takes time to continue and to me it is just an endless headache to check what is done and still after weeks of trying I do not know where I stand. How would I know whether the sync has been properly done and finished?

An additional sync attempt should be quite fast if everything has been already synchronized.

I attempted to have a sync but again it stopped every five minutes with the error message. So in essence I am unable to verify if the sync is perfect or not… What are my other choices as where I stand with syncing of course not really acceptable

I would appreciate a suggestion of what should I do and I really hope that it is not to sync my iPad fully again…

Hold the Option key and choose Help > Report bug to start a support ticket.

I understand what you mean by “real issue” here, but expecting something to synchronize only to have to manually baby-sit repeated attempts to ensure I actually have current data on all devices is, to me, a very real issue.

More frustrating is having to watch the macOS Log window, because the iOS progress spinner cheerfully lies to me, as if data’s still transferring, even after DEVONthink Pro’s Log window indicates “Connection to server timed out”. Which, by the way, typically happens within a minute or so of each attempt to migrate data between my iPad, MacBook, and iPhone.

Actually, it’s not clear which device is telling me something reliable: after DEVONthink Pro’s Log window declares “Connection to server timed out”, the iOS sync spinner graphic continues from database to database, and time-out messages keep getting logged on the Mac.

It’s completely unclear to me what you’re doing. This is like telling you didn’t get from A to B to retrieve a package from a warehouse, but didn’t mention whether you were sailing, driving a heavy truck or flying by jet. DT and DTTG offer various options to synchronize.

Could you elaborate:

  • are other devices involved beside a macOS machine and an iOS device?
  • is synchronization performed directly, over a LAN or over the internet?
  • if applicable: what are your LAN connection speeds?
  • what protocol do you use to synchronize your data?

I did fail to mention many of those things, it’s true. They’re also not relevant. While they might be directly related to the underlying issue(s), none of them are at the root of the problem I’m describing: DTTG failing to accurately inform me of the state of things. It says it’s timed out, yet it continues to sync. Maybe. Or does it? The tiny progress circle fills too slowly to provide any sense of “how much longer?” if there’s any amount of data being moved, the iOS spinner only tells me something’s happening (but not what’s or how much longer it might take)and seems to disagree with what the macOS log windows says.

Sync resumes on its own on an interval.
Also, in DEVONthink To Go, you can long press the sync icon to see sync activity. Have you tried that?