EAP3 + newest Apple update. All mail connection to Exchange are dead now.

Getting Outlook connected to an Exchange server at a remote location was painfully slow since migrating from v17 to v18. Anywhere from 2 minutes to one hour.

Now, with EAP3 + newest Apple update, all mail connections from an Iphone to an Exchange are dead now.

As far as I am concerned, the more v18 progress in time, the uglier it is.

Paul Jr

Parents Reply
  • We need to split this very carefully. 

    Exchange on iPhone and Exchange in outlook is most likely MAPI over http(s). Older versions used RPC over http. So it highly depends on the version, you are using on Client / Exchange. 

    There is no SMTP used in Exchange (as far as i know). https://techcommunity.microsoft.com/t5/Exchange-Team-Blog/Outlook-Connectivity-with-MAPI-over-HTTP/ba-p/586590

    And Exchange has a variety of HTTPs styles. Question one: https://www.ssllabs.com/ssltest/ If you check your Exchange with ssllabs.com (EWS and MAPI), do you have any issues there? 

    Is your Exchange version considered safe? 

     

    "Old school SMTP" is still used for MTA communication. Basically how Exchange will send a mail to another mail server. Considered by IANA.

    There is another mechanism (try) to split SMTP (port 25) from the Client way to send a mail (SMTPs?).

    https://en.wikipedia.org/wiki/SMTPS

    Port 578 or Port 465 are most likely the Client to Server ports, while Port 25 is used MTA to MTA. 

    As far as i know, they split those ports to have a clear split between the Client and server communication but Port 25 is widely used. 

     

     

    To sum this up.

    Ian has an issue with the IMAP / Legacy SMTP Proxy.

    Paul has an issue with DPI Issue hitting on his HTTP(s) traffic. 

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