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[GH-ISSUE #2037] Exchange Server with Nginx Proxy Manager #1472
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Originally created by @azaloum90 on GitHub (May 4, 2022).
Original GitHub issue: https://github.com/NginxProxyManager/nginx-proxy-manager/issues/2037
I have some settings that will supposedly work, but I am unsure how to enter these into NPM. Any ideas?
http://blog.manton.im/2016/04/configure-nginx-with-exchange-2010-2013.html
@mirotrex commented on GitHub (Nov 23, 2022):
Are there any Updates on this issue? @jc21
@azaloum90 commented on GitHub (Nov 23, 2022):
I got nothing back from anyone... Nobody seems to know how to implement it. I gave up and went back to Microsoft Web Application Proxy
@ichilver commented on GitHub (Jun 9, 2023):
I tried adding the below in the NPM advanced tab, and also for each of the locations you mentioned above.
However when I go to https://exchange-server.mydomain.com/owa I get an error 'HTTP Error 400. The request has an invalid header name.'
I connected to the container and went to the logs in /data/logs but I can't see which header its complaining about.
However if you took out the line
proxy_set_header Host $host;it worksWell!!! Works to a point.
What I can't get working is outlook from outside on the Internet when the Exchange IIS server only has "Windows Auth" enabled. If I enable "Basic Auth" it gets a bit further but still doesn't works.
I can see it does the autodiscover stuff ok and then redirects to https://exchange-server.mydomain.com/mapi and asks for a username and password.
I tried domain\username and username@mydomain.com and neither work.
I tried setting the Realm to
exchange-server.mydomain.comandexchange-server.msad.mydomain.comI am missing something for passing the correct type of authentication, but what???
I need to support the "Windows Auth" on the IIS server, but how do I that from NPM?
Any ideas?
Has anyone got MS Exchange working behind a NPM for OWA, ActiveSync and Outlook?
@azaloum90 commented on GitHub (Jun 9, 2023):
You for so much further than I ever did! I'm intrigued as to what else gets in the way of allowing this. I believe the mechanism that needs to function is "Forms Authentication", but not sure what that needs from an http reverse proxy perspective.
Wish MS had more info, I don't think they'll ever consider this a "supported" configuration so I can't ask.
Only other thing I can think of is running Wireshark from my existing Web Application Proxy and doing some pakcey captures
@ichilver commented on GitHub (Jun 9, 2023):
@azaloum90 I think I got all the stuff working for HTTP GET requests and stuff requiring Basic Auth.
What I can't get working is the NTLM auth on /autodiscover and /mapi
I am either missing something in the NPM settings or its just not possible to proxy NTLM auth. Something in the back of my mind is thinking this isn't possible because technically NPM is acting as "a man in the middle". IDK.
@azaloum90 commented on GitHub (Jun 9, 2023):
It's definitely possible because MAPI authentication works fine with Microsoft Web Application Proxy (that's actually a Microsoft-supported configuration, though you are supposed to pass it through ADFS for authentication which I do not). Brings me back to "what's missing in the packets", so I think I'd have to look at the packets traversing:
From Microsoft Web App Proxy
To Exchange
And then compare that with packets traversing:
From NPM
To Exchange
Unfortunately my NPM setup has been turned off for over a year now, but I suppose I could grab some packet captures from my Web App Proxy to Exchange servers and then compare with yours?
@ilya-maltsev commented on GitHub (Jul 27, 2023):
Hi,
try to check that basic authentication enabled for MAPI on Exchange:
https://learn.microsoft.com/en-us/exchange/clients/mapi-over-http/configure-mapi-over-http?view=exchserver-2019
After exec that command:
Set-MapiVirtualDirectory -Identity "<exchange_host>\mapi (Default Web Site)" -ExternalURL https://<mail.domain.com>/mapi -IISAuthenticationMethods NTLM, OAuth , Basicin our case, all works fine
@azaloum90 commented on GitHub (Jan 24, 2024):
Hey, could you by chance show me some screenshots of how you have the configuration entered into NPM? The entry points are rather confusing and I am curious as to what your configuration is.
@ilya-maltsev commented on GitHub (Jan 24, 2024):
@azaloum90
that command must be directly executed on Windows Server with installed Exchange via Powershell
@azaloum90 commented on GitHub (Jan 24, 2024):
Hey,
I'm aware of that piece, I'm just curious how you have the rest of the configuration entered into NPM?
@ilya-maltsev commented on GitHub (Jan 24, 2024):
@azaloum90 Look at magic lines
@azaloum90 commented on GitHub (Jan 29, 2024):
Thanks for this. How many entries for your mail server? just a mail.domain.com entry?
@vtornik commented on GitHub (Feb 6, 2024):
Thanks for this. Could you tell me how to perform this configuration in the Nginx proxy manager interface? How and in which tab should this be specified?



@azaloum90 commented on GitHub (Feb 6, 2024):
I am wondering the same... @ilya-maltsev if you know please let us know.
@ilya-maltsev commented on GitHub (Feb 6, 2024):
https://develop.nginxproxymanager.com/advanced-config/#custom-nginx-configurations
@azaloum90 commented on GitHub (Feb 6, 2024):
Given this info, is it safe to assume that the info should go into this screenshot?

@vtornik commented on GitHub (Feb 6, 2024):
Thank you. Do I understand correctly that I have to create
a /data/nginx/custom/http_top.conf file
with this content:
map $status $forceBasicOutlook{ #magic_line
401 'Basic realm=$host'; #magic_line
} #magic_line
and
the /data/nginx/custom/server_proxy.conf file
with the contents:
@azaloum90 commented on GitHub (Apr 22, 2024):
@ilya-maltsev ,
Would you be able to post your entire configuration, as well as perhaps with screenshots as to where these configurations are entered (obviously with domain names redacted)? Though your info was helpful, I am unable to make this work with a variety of configurations -- NPM is reporting that my host is offline, likely due to the configuration being mis-scripted.
Any help is greatly appreciated!
Adam
@ilya-maltsev commented on GitHub (Apr 22, 2024):
@azaloum90
Did you look at https://develop.nginxproxymanager.com/advanced-config/#custom-nginx-configurations
?
Advanced configuration must be did through config files of nginx, not through web-ui of NPM...
Unfortunately I can't show my config files of nginx...
@tarocjsu commented on GitHub (May 6, 2024):
Useless discussion....
@github-actions[bot] commented on GitHub (Nov 26, 2024):
Issue is now considered stale. If you want to keep it open, please comment 👍
@TrentSteenholdt commented on GitHub (Sep 10, 2025):
https://blog.cortanadesign.com.au/2025/09/10/how_to_get_exchange_2019_working_behind_nginx_proxy_manager
@azaloum90 commented on GitHub (Sep 12, 2025):
Wow, this is incredible, thank you!
I tried to use your compose file and am getting an error message that either a login is required, or that the docker repository does not exist (clearly not the case). Am I doing something wrong here?
@TrentSteenholdt commented on GitHub (Sep 17, 2025):
https://hub.docker.com/r/greetoz/npm-ntlm I wouldn't trust your shortened image name for pulling the right one :-)
@azaloum90 commented on GitHub (Sep 17, 2025):
The only way I was able to get this to work was removing the ":latest" from the command, after which it pulled as expected.
Still having some issues with the config, might have to message you separately for that one :)
Get Outlook for Androidhttps://aka.ms/AAb9ysg
From: Trent Steenholdt @.>
Sent: Wednesday, September 17, 2025 7:18:09 AM
To: NginxProxyManager/nginx-proxy-manager @.>
Cc: azaloum90 @.>; Mention @.>
Subject: Re: [NginxProxyManager/nginx-proxy-manager] Exchange Server with Nginx Proxy Manager (Issue #2037)
[https://avatars.githubusercontent.com/u/47766435?s=20&v=4]TrentSteenholdt left a comment (NginxProxyManager/nginx-proxy-manager#2037)https://github.com/NginxProxyManager/nginx-proxy-manager/issues/2037#issuecomment-3302518936
https://blog.cortanadesign.com.au/2025/09/10/how_to_get_exchange_2019_working_behind_nginx_proxy_manager
Wow, this is incredible, thank you!
I tried to use your compose file and am getting an error message that either a login is required, or that the docker repository does not exist (clearly not the case). Am I doing something wrong here?
[Image]https://private-user-images.githubusercontent.com/8965127/489016839-5c6899ab-39a3-4f4b-95dd-504c31e3c54a.png?jwt=eyJ0eXAiOiJKV1QiLCJhbGciOiJIUzI1NiJ9.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.sZYSRryC1Hbv9f8iSLgtg9qWuc5VCTLl3wxyjbRaxqo [Image] https://private-user-images.githubusercontent.com/8965127/489016738-80a282f2-600a-4d50-92b5-7788f68000ed.png?jwt=eyJ0eXAiOiJKV1QiLCJhbGciOiJIUzI1NiJ9.eyJpc3MiOiJnaXRodWIuY29tIiwiYXVkIjoicmF3LmdpdGh1YnVzZXJjb250ZW50LmNvbSIsImtleSI6ImtleTUiLCJleHAiOjE3NTgxMDc5MjMsIm5iZiI6MTc1ODEwNzYyMywicGF0aCI6Ii84OTY1MTI3LzQ4OTAxNjczOC04MGEyODJmMi02MDBhLTRkNTAtOTJiNS03Nzg4ZjY4MDAwZWQucG5nP1gtQW16LUFsZ29yaXRobT1BV1M0LUhNQUMtU0hBMjU2JlgtQW16LUNyZWRlbnRpYWw9QUtJQVZDT0RZTFNBNTNQUUs0WkElMkYyMDI1MDkxNyUyRnVzLWVhc3QtMSUyRnMzJTJGYXdzNF9yZXF1ZXN0JlgtQW16LURhdGU9MjAyNTA5MTdUMTExMzQzWiZYLUFtei1FeHBpcmVzPTMwMCZYLUFtei1TaWduYXR1cmU9N2FkNWM0ZjU4MDIyYzc4NGFjODA0NzMwNzYxZGNkMGQ5Yjk3NmQzY2E0NWI0ZTA3Mjc1ZDk2MGJmMjczMTI0OCZYLUFtei1TaWduZWRIZWFkZXJzPWhvc3QifQ.8AOVXW1f8jKjQqO6rq4bsbcgWGke85lHXQLx8vKF4Q8
https://hub.docker.com/r/greetoz/npm-ntlm I wouldn't trust your shortened image name for pulling the right one :-)
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@azaloum90 commented on GitHub (Oct 14, 2025):
Hi!
So I got to "Defining the NTLM Upstream" part of your guide using this YAML config:
`services:
app:
image: 'docker.io/greetoz/npm-ntlm:latest'
labels:
- "com.centurylinklabs.watchtower.enable=true"
restart: unless-stopped
ports:
# These ports are in format :
- '80:80' # Public HTTP Port
- '443:443' # Public HTTPS Port
- '81:81' # Admin Web Port
# Add any other Stream port you want to expose
- '32400:32400' # Plex
`
I am getting this error in the logs:
Basic searches show that this means it can't seem to utilize the NTLM module within the container.
Is there something that I am missing?
@trentsteenholdt-synergyau commented on GitHub (Oct 14, 2025):
Asking the real basic question, but are you sure your docker image has been composed with the right image? E.g.
docker-compose up -dAlso it could just be the formatting, but make sure your compose file is formatted exactly with the right indents etc.
Here is mine
Might be the missing piece is the dynamic-mods reference.
@azaloum90 commented on GitHub (Oct 25, 2025):
Confirmed, the lack of the "20-dynamic-mods.conf" configuration file with the information you provided on the host as you noted is what caused the error below. Once I added that to the Docker configuration, all was functional:
nginx: [emerg] unknown directive "ntlm" in /data/nginx/custom/http_top.conf:4Other item I did not realize was that your Nginx Configuration for use in the NPM Web portal requires actual FQDNs, not just ip address. The box I am using is destined to be on a DMZ network, so there is no available DNS server that has the FQDN's availabile. I set up DNSMasq via another docker container on the same system and all "host not found" errors disappeared, and NPM now shows the Exchange .
At this point in time, the only thing I have not yet done is utilize an Azure Tenant for the Entra ID App Registration / connectivity into my domain. Have you had any luck getting this to work without that component? I am using an Exchange ActiveSync Mail Client (eMClient Mail application) and it just keeps kicking back "Unauthorized" when I try to utilize NPM for connectivity,
@azaloum90 commented on GitHub (Nov 8, 2025):
Just wanted to reach out one last time. Have you had any issues with the OAB throwing errors for connectivty? I have done the entire config you noted except for the HMA piece, and everything works flawlessly -- mobile clients, outlook, 3rd party mail clients ----- EXCEPT when trying to download the Offline Address Book, then both Outlook and the 3rd party mail clients throw errors. Outlook prompts for credentials regularly because of this. I've worked around it for now by using a 3rd party mail client where I can disable download of the OAB, but I am wondering what else can be added to the /OAB portion of the config to prevent this issue.
Feel free to email me at myusername @ gee-mayle.c0m
Thanks!
Adam