- CONNECT SECURESERVER TO OUTLOOK FOR MAC 2011 UPDATE
- CONNECT SECURESERVER TO OUTLOOK FOR MAC 2011 WINDOWS
So the issue appears to be the use of an unsupported, insecure, outdated, obsolete protocol in the SSL handshake in Outlook 2011. I unchecked that, clicked Apply and the emails began to flush through. Sure enough, in the Content Filter appeared a new option: "Drop connection when HTTPS connection with SSL V3 or previous version". I knew that the firmware on the firewall had just been updated, so I set about hunting for a rule or something that may be affecting SSLv2 packets. In contrast, Apple Mail would send the "Client Hello" in a TLSv1.2 packet and receive a prompt response, allowing it to complete the SSL handshake and begin syncing with the Exchange server. When using local communication that didn't touch the firewall, the SSL handshake goes on to completion having negotiated the use of TLSv1 instead of SSLv2. Outlook 2011 would send the "Client Hello" in an SSLv2 packet, after which point it would receive no communication from the server (despite having just successfully negotiated a TCP handshake with the server, therefore connectivity wasn't an issue). Next, I used Wireshark to trace the packets when attempting to instantiate the connection to the server from both Outlook 2011 and Apple Mail. I tested using Apple Mail which brought through the emails fine, so I knew that the problem existed between the firewall and the Outlook 2011 application. Both site-to-site VPN and internet were not allowing their emails to sync with their mail server. The only common denominator was the firewall, a ZyXel USG 310. However, we discovered when a user from the group company was attempting to get their emails through that this was still an issue (different site, domain and Exchange servers). This initially started working after setting a DNS record for the public FQDN to point at the local IP.
Are there some services I can restart to test this? It seems like there's a problem with EWS or autodiscover.
CONNECT SECURESERVER TO OUTLOOK FOR MAC 2011 UPDATE
We either need to update the server to the public address ( ) before they leave, or they need to connect to the VPN to receive mail, neither of which is the ideal behaviour. However, some of the users need to take their machine off site, which presents a problem. Specifying the public address ( ) used to work just fine before the servers were rebooted, however this isn't the case anymore.įor the most part this isn't a problem, because the vast majority of machines with Outlook 2011 are iMacs or Mac Minis, which don't leave the site anyway, so we've just changed the value of the server field to the local address and they can carry on.
When users are in the office, the Microsoft Exchange server field must specify the local address of the server ( ), otherwise it will not connect.
CONNECT SECURESERVER TO OUTLOOK FOR MAC 2011 WINDOWS
All Outlook versions for Windows are still working, as is Outlook 2016 for Mac. The issue is only localised to Outlook 2011. We're experiencing a strange issue with all of the Macs running Outlook 2011 since we had to power down the whole site for the installation of an electricity meter.
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