Outlook exchange not auto updating

29-Apr-2020 06:05

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After about 5 events Outlook would keep spamming retransmit and Exchange would not see any come in, however Exchange would still see the pings and rdp connections from the test workstations (as that was still working). VPN flaps again 10 minutes later and Outlook is broken again.Sit and wait; exactly 30 minutes after the last VPN flap Outlook reconnects on its own, everything sitting in the Outbox is sent, and everything inbound (and showing in OWA) is then delivered to Outlook.The general guidance from the product team is that the value, ideally, ought to be 30 minutes (and no less that 15 minutes): https://blogs.technet.microsoft.com/exc ...-premises/So you could give that a shot with a couple of workstations to see if it helps with the problem. If connectivity is lost between outlook and exchange, this happens.Who knows, it could be something like ipv6 traffic when you are expecting ipv4, which may have different firewall rules or different routes through the network...

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Has anyone in The Great Ars Hivemind run into something similar?If that restore the connecting, then my theory might be correct. Hitting Reconnect on the Connection Status window, hitting send/receive, and hitting Work Offline/Online don't help.For example, hitting Reconnect shows everything reconnect but Outlook still shows "sending message" and the systray icon has the hourglass on it and mousing over shows the message "Microsoft Outlook is requesting data from the server".It took me 2 days to collect all of this, and then another 4 days (including weekend) to convince the Exchange Admin and the Network Engineer that they need to sit down together and fix this.

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For the interim the Network Engineer rebuilt the VPN tunnel (there has been no flapping since) and he added a "no-sync" setting to the firewall which apparently forces a new tcp session for all "no-sync" packets (thats outside of my expertise so I'll take his word for it).

If your clients are using ipv6, be aware that some firewalls may require additional configuration for ipv6 rules.