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I've set up an apache reverse proxy for our exchange 2013 server. Outlook anywhere works fine, infact all android, IOS and windows decices connect no problem. The only problem we are having is with MacOS devices with Outlook for mac, they use EWS instead of outlook anywhere.

This is a snippet of the apache access log:

5.170.197.216 - - [15/Dec/2016:16:00:15 +0100] "POST /ews/exchange.asmx HTTP/1.1" 401 3844 "-" "MacOutlook/15.29.0.161209 (Intelx64 Mac OS X Version 10.12.1 (Build 16B2555))"
5.170.197.216 - - [15/Dec/2016:16:00:15 +0100] "POST /ews/exchange.asmx HTTP/1.1" 401 965 "-" "MacOutlook/15.29.0.161209 (Intelx64 Mac OS X Version 10.12.1 (Build 16B2555))"
5.170.197.216 - - [15/Dec/2016:16:00:15 +0100] "POST /ews/exchange.asmx HTTP/1.1" 200 7054 "-" "MacOutlook/15.29.0.161209 (Intelx64 Mac OS X Version 10.12.1 (Build 16B2555))"
5.170.197.216 - - [15/Dec/2016:16:00:15 +0100] "POST /ews/exchange.asmx HTTP/1.1" 401 402 "-" "MacOutlook/15.29.0.161209 (Intelx64 Mac OS X Version 10.12.1 (Build 16B2555))"
5.170.197.216 - - [15/Dec/2016:16:00:15 +0100] "POST /ews/exchange.asmx HTTP/1.1" 401 965 "-" "MacOutlook/15.29.0.161209 (Intelx64 Mac OS X Version 10.12.1 (Build 16B2555))"
5.170.197.216 - - [15/Dec/2016:16:00:15 +0100] "POST /ews/exchange.asmx HTTP/1.1" 200 2139 "-" "MacOutlook/15.29.0.161209 (Intelx64 Mac OS X Version 10.12.1 (Build 16B2555))"
5.170.197.216 - - [15/Dec/2016:16:00:15 +0100] "POST /ews/exchange.asmx HTTP/1.1" 401 402 "-" "MacOutlook/15.29.0.161209 (Intelx64 Mac OS X Version 10.12.1 (Build 16B2555))"
5.170.197.216 - - [15/Dec/2016:16:00:15 +0100] "POST /ews/exchange.asmx HTTP/1.1" 401 965 "-" "MacOutlook/15.29.0.161209 (Intelx64 Mac OS X Version 10.12.1 (Build 16B2555))"
5.170.197.216 - - [15/Dec/2016:16:00:16 +0100] "POST /ews/exchange.asmx HTTP/1.1" 200 2164 "-" "MacOutlook/15.29.0.161209 (Intelx64 Mac OS X Version 10.12.1 (Build 16B2555))"
5.170.197.216 - - [15/Dec/2016:16:00:16 +0100] "POST /ews/exchange.asmx HTTP/1.1" 401 540 "-" "MacOutlook/15.29.0.161209 (Intelx64 Mac OS X Version 10.12.1 (Build 16B2555))"
5.170.197.216 - - [15/Dec/2016:16:00:16 +0100] "POST /ews/exchange.asmx HTTP/1.1" 401 540 "-" "MacOutlook/15.29.0.161209 (Intelx64 Mac OS X Version 10.12.1 (Build 16B2555))"
5.170.197.216 - - [15/Dec/2016:16:00:16 +0100] "POST /ews/exchange.asmx HTTP/1.1" 401 402 "-" "MacOutlook/15.29.0.161209 (Intelx64 Mac OS X Version 10.12.1 (Build 16B2555))"
5.170.197.216 - - [15/Dec/2016:16:00:16 +0100] "POST /ews/exchange.asmx HTTP/1.1" 401 540 "-" "MacOutlook/15.29.0.161209 (Intelx64 Mac OS X Version 10.12.1 (Build 16B2555))"
5.170.197.216 - - [15/Dec/2016:16:00:16 +0100] "POST /ews/exchange.asmx HTTP/1.1" 401 540 "-" "MacOutlook/15.29.0.161209 (Intelx64 Mac OS X Version 10.12.1 (Build 16B2555))"
5.170.197.216 - - [15/Dec/2016:16:00:16 +0100] "POST /ews/exchange.asmx HTTP/1.1" 401 965 "-" "MacOutlook/15.29.0.161209 (Intelx64 Mac OS X Version 10.12.1 (Build 16B2555))"
5.170.197.216 - - [15/Dec/2016:16:00:16 +0100] "POST /ews/exchange.asmx HTTP/1.1" 401 965 "-" "MacOutlook/15.29.0.161209 (Intelx64 Mac OS X Version 10.12.1 (Build 16B2555))"
5.170.197.216 - - [15/Dec/2016:16:00:16 +0100] "POST /ews/exchange.asmx HTTP/1.1" 401 965 "-" "MacOutlook/15.29.0.161209 (Intelx64 Mac OS X Version 10.12.1 (Build 16B2555))"
5.170.197.216 - - [15/Dec/2016:16:00:16 +0100] "POST /ews/exchange.asmx HTTP/1.1" 401 965 "-" "MacOutlook/15.29.0.161209 (Intelx64 Mac OS X Version 10.12.1 (Build 16B2555))"
5.170.197.216 - - [15/Dec/2016:16:00:16 +0100] "POST /ews/exchange.asmx HTTP/1.1" 401 965 "-" "MacOutlook/15.29.0.161209 (Intelx64 Mac OS X Version 10.12.1 (Build 16B2555))"
5.170.197.216 - - [15/Dec/2016:16:00:16 +0100] "POST /ews/exchange.asmx HTTP/1.1" 401 386 "-" "MacOutlook/15.29.0.161209 (Intelx64 Mac OS X Version 10.12.1 (Build 16B2555))"
5.170.197.216 - - [15/Dec/2016:16:00:16 +0100] "POST /ews/exchange.asmx HTTP/1.1" 200 12566 "-" "MacOutlook/15.29.0.161209 (Intelx64 Mac OS X Version 10.12.1 (Build 16B2555))"
5.170.197.216 - - [15/Dec/2016:16:00:16 +0100] "POST /ews/exchange.asmx HTTP/1.1" 200 22043 "-" "MacOutlook/15.29.0.161209 (Intelx64 Mac OS X Version 10.12.1 (Build 16B2555))"
5.170.197.216 - - [15/Dec/2016:16:00:16 +0100] "POST /ews/exchange.asmx HTTP/1.1" 401 386 "-" "MacOutlook/15.29.0.161209 (Intelx64 Mac OS X Version 10.12.1 (Build 16B2555))"
5.170.197.216 - - [15/Dec/2016:16:00:16 +0100] "POST /ews/exchange.asmx HTTP/1.1" 401 402 "-" "MacOutlook/15.29.0.161209 (Intelx64 Mac OS X Version 10.12.1 (Build 16B2555))"
5.170.197.216 - - [15/Dec/2016:16:00:16 +0100] "POST /ews/exchange.asmx HTTP/1.1" 200 1973 "-" "MacOutlook/15.29.0.161209 (Intelx64 Mac OS X Version 10.12.1 (Build 16B2555))"
5.170.197.216 - - [15/Dec/2016:16:00:16 +0100] "POST /ews/exchange.asmx HTTP/1.1" 401 965 "-" "MacOutlook/15.29.0.161209 (Intelx64 Mac OS X Version 10.12.1 (Build 16B2555))"
5.170.197.216 - - [15/Dec/2016:16:00:16 +0100] "POST /ews/exchange.asmx HTTP/1.1" 401 386 "-" "MacOutlook/15.29.0.161209 (Intelx64 Mac OS X Version 10.12.1 (Build 16B2555))"
5.170.197.216 - - [15/Dec/2016:15:58:43 +0100] "POST /ews/exchange.asmx HTTP/1.1" 200 4384 "-" "MacOutlook/15.29.0.161209 (Intelx64 Mac OS X Version 10.12.1 (Build 16B2555))"

As you can see the client is calling /ews/exchange.asmx a lot in 2 seconds, sometimes apache gives a 200 but mostly a 401. Infact the effect on the client side is that it seems to work for a moment and then disconnects.

Any ideas what this could be?

Thanks in advance for any help, James

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  • We tried to use an Apache as well in the past and wasted a lot of time, but it NEVER was working successfully and caused only issues. So we switched over to use a Microsoft Web Application Proxy. I know no solution only shared pain ...
    – BastianW
    Dec 15, 2016 at 16:23
  • You couldn't get anything working? I've got it all, anywhere, owa, autodiscover ecc. Only problem is ews used by outlook for mac. I actually just donwloaded ews editor and connected no probs, it's something that outlook 2016 for mac is doing. Probably some set env or something in my apache config would fix it just don't know where to start from.
    – James
    Dec 15, 2016 at 16:29
  • We got it working for OWA, AutoDiscover, OAW, iPhone (but no Android) and had issues with the MACOS as well. But the iPhone broke after we applied an Exchange Servicepack. However at the same time the latest Android versions started to work without change on the Apache RP. So we tried to open a case with Microsoft but it was closed as Apache RPs aren´t supported by them. So in the end we where alone and switched over to a MS supported solution.
    – BastianW
    Dec 15, 2016 at 16:34
  • And now you've got it all working? By all i mean the following: Outlook for windows, Outlook for Mac, Android, IOS?
    – James
    Dec 15, 2016 at 16:47
  • No, as said we are using now the Microsoft Web Application Proxy. With Apache we gave up as to many user got upset.
    – BastianW
    Dec 15, 2016 at 17:20

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