Bonjour sync problems

Why, when I can easily share files on my network between my ethernet-wired iMac and my Wi-Fi-connected MacBook Pro, does DEVONthink’s Bonjour sync often take ages to connect, sometimes not succeeding until I employ some workaround, like turning Wi-Fi off and then on again on the MacBook Pro? I get log alerts saying things like, “Attempt to connect to host timed out - AsyncSocketErrorDomain 2”, which can happen while I’m transferring files by regular file sharing.

When’s the last time you rebooted the Mac?

The iMac? Terminal says 9 days ago.

And how soon after a reboot are you having Bonjour issues?

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As far as I can recall, anytime after a reboot, but I don’t really know. I’d have to test that methodically to find out.

What’s the suspicion or reasoning behind you asking?

Sometimes the operating system gets “confused” and needs to be re-booted to start fresh. Worth a try.

I know the feeling.

It’s possible for a Bonjour port to stall.
Quitting and relaunching the application may not be enough, but it’s the first step.
If there’s no resolution, a machine reboot usually resolves it.

Note: The stall isn’t all that common and may even resolve on its own.

hello-it-turn-off-on-again

A reboot solved it — temporarily: the problem returns intermittently.
The port on the iMac is 51550. Might it be changed?

Unless you’ve chosen that one yourself, DEVONthink dynamically assigns a random open port.
You can go into the Preferences > Sync > Bonjour Options and set one yourself or clear the number and press OK. If you don’t specify one, a new random port will be chosen.