Outlook For Mac 2011 Cannot Connect To Exchange Server

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Outlook For Mac 2011 Cannot Connect To Exchange Server 5,9/10 2839 votes

In of this article, we discussed symptoms of Mac Mail unable to connect to Exchange 2016 servers through KEMP LoadMaster load balancers. We also discussed troubleshooting steps that addressed the issue of ExRCA.com unable to pass EWS tests, however, we stopped there since Mac Mail failed to connect despite ExRCA EWS tests passed. Let’s see what we can do to get the Mac Mail to connect successfully to Exchange servers. Since we addressed the 100-continue handling in of this article, ExRCA tests did not indicate any more issues. Microsoft Outlook for Mac did not have issue connecting to Exchange even before we changed 100-continue handling to be RFC-7231 compliant. At this point, I decided to look at the network trace. Looking at the trace captured using Wireshark on the client machine, I noticed the following HTTP dialog: POST /ews/exchange.asmx 401 Unauthorized POST /ews/exchange.asmx 200 OK POST /ews/exchange.asmx 401 Unauthorized POST /ews/exchange.asmx 401 Unauthorized POST /ews/exchange.asmx 400 Bad Request Notice how initial dialog included challenge response for NTLM authentication and ended with 200 OK.

At this point Mac Mail client started with another POST operation to EWS. However, this time the pattern followed multiple 401 responses from server and ended with 400. When comparing that with Outlook for Mac, the pattern looked like the following: POST /ews/exchange.asmx 401 Unauthorized POST /ews/exchange.asmx 401 Unauthorized POST /ews/exchange.asmx 200 OK Notice how the pattern looks similar to Mac Mail’s second POST request, however, it ends with 200 OK. The response included data that was requested by POST operation. I needed to correlate this with the data being received on the Exchange server. Due to newer ciphers which use PFS (Perfect Forward Secrecy) I couldn’t decrypt data being received from load balancer by the server despite having the private key used to encrypt the information.

I was able to decrypt client side traffic due to load balancer configuration of ciphers that didn’t use PFS. I don’t recommend this configuration in production and KEMP LoadMaster default setup uses more secure ciphers. I had it configured this way only for troubleshooting purpose in my lab and no production data was in flight during testing. I was now facing the issue of capturing the headers from the server side. One way to address this is to configure list of ciphers used by server similar to what I had done on KEMP LoadMaster. However, in my test that did not work for some reason.

Teac drivers for mac. I decided to use failed request tracing in IIS (big thanks to my Microsoft colleague Brad Hughes for the hint).

My Microsoft Outlook office 2011: for mac is not connecting to my exchange server. It worked when I installed, and stopped the next morning, spend 3 hours trying to solve the issue, and even ended up uninstalling, the program twice.

Cannot connect to exchange server

Iphone Cannot Connect To Exchange Server

I had contact with a Twitter user on an issue with Outlook for Mac 2011 talking against Exchange Server 2007 on Small Business Server 2008. When configuring a new account, Outlook for Mac reported “Account cannot be added. Note that Outlook 2011 requires Exchange Server 2007 SP1 Update Rollup 4 or later.” However, that couldn’t be right because that user claimed to be running a higher version of Exchange 2007. After manually entering the server name, a connection could be established and an initial download of folders and contents took place. However, items weren’t updated and contacts and calendar remained empty. After trying and checking some things, I asked to turn on Outlook for Mac’s logging hoping to find something in the Exchange Web Services log (Outlook for Mac 2011 is EWS based). You can enable logging by checking Window > Error Log > Errors > Settings > Turn on logging for troubleshooting.