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Going back to your original message…

Originally Posted by coldrick View Post
I used to have no problem syncing Omnifocus on my laptop to the desktop using the proxy, whereas the iPhone sync would fail.

Now, however, both the iPhone (1.5.3) sync and laptop (1.7.3) sync fail with "Unable to synchronize database with server: there was a problem communicating with the secure web proxy server (HTTPS)"
Are there any additional details about the failure logged to the Console on the Mac? (You'll find in /Applications/Utilities.)

Are you still able to sync through the proxy server if you use an earlier release of OmniFocus? (You can download an earlier release from our Release Archive.) If so, it might help us pinpoint the problem if you could tell us the last release which worked / first release which didn't work.