Skip to content

Exchange Server with Nginx Proxy Manager #2037

Description

@azaloum90

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

server {
  listen 192.168.0.1:443 ssl;
  server_name owa.myserver.com;
  ssl_certificate /etc/nginx/ssl/cert.pem;
  ssl_certificate_key /etc/nginx/ssl/key.key;
  access_log  /var/log/nginx/mydomain.access.log  combined;
  error_log  /var/log/nginx/mydomain.error.log;
  client_max_body_size 3G;
  proxy_request_buffering off;
  ssl_session_timeout     5m;
  tcp_nodelay on;
    proxy_http_version      1.1;
    proxy_read_timeout      360;
    proxy_pass_header       Date;
    proxy_pass_header       Server;
    proxy_pass_header      Authorization;
    proxy_set_header        Host $host;
    proxy_set_header        X-Real-IP $remote_addr;
    proxy_set_header        X-Forwarded-For  $proxy_add_x_forwarded_for;
    proxy_pass_request_headers on;
    more_set_input_headers 'Authorization: $http_authorization';
    proxy_set_header Accept-Encoding "";
    more_set_headers -s 401 'WWW-Authenticate: Basic realm="fqdnofyourexchangeserver"';
    proxy_buffering off;
    proxy_set_header Connection "Keep-Alive";
  location / {
  return 301 https://owa.myserver.com/owa;
  }
  location ~* ^/owa { proxy_pass https://fqdnofyourexchangeserver; }
  location ~* ^/Microsoft-Server-ActiveSync { proxy_pass https://fqdnofyourexchangeserver; }
  location ~* ^/ecp { proxy_pass https://fqdnofyourexchangeserver; }
  location ~* ^/rpc { proxy_pass https://fqdnofyourexchangeserver; }
}
# redirect all http traffic to https
server {
  listen 80;
  server_name owa.myserver.com;
  return 301 https://$host$request_uri;
}

Activity

  1. mirotrex commented on Nov 23, 2022

    @mirotrex

    Are there any Updates on this issue? @jc21

  2. azaloum90 commented on Nov 23, 2022

    @azaloum90
    Author

    Are there any Updates on this issue? @jc21

    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

  3. ichilver commented on Jun 9, 2023

    @ichilver

    I tried adding the below in the NPM advanced tab, and also for each of the locations you mentioned above.

    /
    /owa
    /ecp
    /rpc
    /Microsoft-Server-ActiveSync
    /mapi
    
    client_max_body_size   3G;
    tcp_nodelay   on;
    
    proxy_request_buffering off;
    proxy_buffering off;
    
    proxy_http_version     1.1;
    proxy_read_timeout     3600;
    
    proxy_pass_request_headers on;
    proxy_pass_header Date;
    proxy_pass_header Server;
    proxy_pass_header Authorization;
    
    proxy_set_header Host $host;
    proxy_set_header X-Forwarded-Proto https;
    proxy_set_header X-Real-IP $remote_addr;
    proxy_set_header X-Forwarded-For $proxy_add_x_forwarded_for;
    proxy_set_header Connection "Keep-Alive";
    proxy_set_header Accept-Encoding "";
    
    more_set_input_headers 'Authorization: $http_authorization';
    more_set_headers -s 401 'WWW-Authenticate: Basic realm="exchange-server.mydomain.com"';
    

    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 works

    Well!!! Works to a point.

    • I have OWA webaccess working.
    • I have ECP working, although I soon redirected that as I don't want the ECP publicly accessible
    • I even seem to have ActiveSync working as I am running Nine from Android App store and that connects too.

    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.com and exchange-server.msad.mydomain.com

    I 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?

  4. azaloum90 commented on Jun 9, 2023

    @azaloum90
    Author

    I tried adding the below in the NPM advanced tab, and also for each of the locations you mentioned above.

    /
    /owa
    /ecp
    /rpc
    /Microsoft-Server-ActiveSync
    /mapi
    
    client_max_body_size   3G;
    tcp_nodelay   on;
    
    proxy_request_buffering off;
    proxy_buffering off;
    
    proxy_http_version     1.1;
    proxy_read_timeout     3600;
    
    proxy_pass_request_headers on;
    proxy_pass_header Date;
    proxy_pass_header Server;
    proxy_pass_header Authorization;
    
    proxy_set_header Host $host;
    proxy_set_header X-Forwarded-Proto https;
    proxy_set_header X-Real-IP $remote_addr;
    proxy_set_header X-Forwarded-For $proxy_add_x_forwarded_for;
    proxy_set_header Connection "Keep-Alive";
    proxy_set_header Accept-Encoding "";
    
    more_set_input_headers 'Authorization: $http_authorization';
    more_set_headers -s 401 'WWW-Authenticate: Basic realm="exchange-server.mydomain.com"';
    

    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 works

    Well!!! Works to a point.

    • I have OWA webaccess working.
    • I have ECP working, although I soon redirected that as I don't want the ECP publicly accessible
    • I even seem to have ActiveSync working as I am running Nine from Android App store and that connects too.

    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.com and exchange-server.msad.mydomain.com

    I 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?

    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

  5. ichilver commented on Jun 9, 2023

    @ichilver

    @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.

  6. azaloum90 commented on Jun 9, 2023

    @azaloum90
    Author

    @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.

    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?

  7. ilya-maltsev commented on Jul 27, 2023

    @ilya-maltsev

    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 , Basic
    in our case, all works fine

  8. azaloum90 commented on Jan 24, 2024

    @azaloum90
    Author

    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 , Basic in our case, all works fine

    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.

  9. ilya-maltsev commented on Jan 24, 2024

    @ilya-maltsev

    @azaloum90
    that command must be directly executed on Windows Server with installed Exchange via Powershell

  10. azaloum90 commented on Jan 24, 2024

    @azaloum90
    Author

    @azaloum90 that command must be directly executed on Windows Server with installed Exchange via Powershell

    Hey,

    I'm aware of that piece, I'm just curious how you have the rest of the configuration entered into NPM?

  11. ilya-maltsev commented on Jan 24, 2024

    @ilya-maltsev

    @azaloum90 Look at magic lines

    http {
    
    map $status $forceBasicOutlook{         #magic_line
            401    'Basic realm=$host';     #magic_line
    }                                       #magic_line
    
    }
    
    server {
    ...
        keepalive_timeout 3h;
        proxy_read_timeout 3h;
    
        proxy_pass_header       Date;
        proxy_pass_header       Server;
        proxy_pass_header       Authorization;
    
        proxy_hide_header WWW-Authenticate;                      #magic_line
        add_header WWW-Authenticate $forceBasicOutlook always;   #magic_line
    
        proxy_buffering off;
        proxy_http_version 1.1;
        proxy_request_buffering off;
        proxy_set_header Connection "Keep-Alive";
    
    ...
    }
    
  12. azaloum90 commented on Jan 29, 2024

    @azaloum90
    Author

    @azaloum90 Look at magic lines

    http {
    
    map $status $forceBasicOutlook{         #magic_line
            401    'Basic realm=$host';     #magic_line
    }                                       #magic_line
    
    }
    
    server {
    ...
        keepalive_timeout 3h;
        proxy_read_timeout 3h;
    
        proxy_pass_header       Date;
        proxy_pass_header       Server;
        proxy_pass_header       Authorization;
    
        proxy_hide_header WWW-Authenticate;                      #magic_line
        add_header WWW-Authenticate $forceBasicOutlook always;   #magic_line
    
        proxy_buffering off;
        proxy_http_version 1.1;
        proxy_request_buffering off;
        proxy_set_header Connection "Keep-Alive";
    
    ...
    }
    

    Thanks for this. How many entries for your mail server? just a mail.domain.com entry?

  13. vtornik commented on Feb 6, 2024

    @vtornik

    @azaloum90 Look at magic lines

    http {
    
    map $status $forceBasicOutlook{         #magic_line
            401    'Basic realm=$host';     #magic_line
    }                                       #magic_line
    
    }
    
    server {
    ...
        keepalive_timeout 3h;
        proxy_read_timeout 3h;
    
        proxy_pass_header       Date;
        proxy_pass_header       Server;
        proxy_pass_header       Authorization;
    
        proxy_hide_header WWW-Authenticate;                      #magic_line
        add_header WWW-Authenticate $forceBasicOutlook always;   #magic_line
    
        proxy_buffering off;
        proxy_http_version 1.1;
        proxy_request_buffering off;
        proxy_set_header Connection "Keep-Alive";
    
    ...
    }
    

    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?
    1-npm-details
    2-npm-custom location
    3-npm-Advanced

  14. azaloum90 commented on Feb 6, 2024

    @azaloum90
    Author

    @azaloum90 Look at magic lines

    http {
    
    map $status $forceBasicOutlook{         #magic_line
            401    'Basic realm=$host';     #magic_line
    }                                       #magic_line
    
    }
    
    server {
    ...
        keepalive_timeout 3h;
        proxy_read_timeout 3h;
    
        proxy_pass_header       Date;
        proxy_pass_header       Server;
        proxy_pass_header       Authorization;
    
        proxy_hide_header WWW-Authenticate;                      #magic_line
        add_header WWW-Authenticate $forceBasicOutlook always;   #magic_line
    
        proxy_buffering off;
        proxy_http_version 1.1;
        proxy_request_buffering off;
        proxy_set_header Connection "Keep-Alive";
    
    ...
    }
    

    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? 1-npm-details 2-npm-custom location 3-npm-Advanced

    I am wondering the same... @ilya-maltsev if you know please let us know.

  15. 3 remaining items

  16. ilya-maltsev commented on Apr 22, 2024

    @ilya-maltsev

    @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...

    If you are a more advanced user, you might be itching for extra Nginx customizability.
    
    NPM has the ability to include different custom configuration snippets in different places.
    
    You can add your custom configuration snippet files at /data/nginx/custom as follow:
    

    Unfortunately I can't show my config files of nginx...

  17. tarocjsu commented on May 6, 2024

    @tarocjsu

    Useless discussion....

  18. github-actions commented on Nov 26, 2024

    @github-actions

    Issue is now considered stale. If you want to keep it open, please comment 👍

  19. azaloum90 commented on Sep 12, 2025

    @azaloum90
    Author

    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 Image
  20. TrentSteenholdt commented on Sep 17, 2025

    @TrentSteenholdt

    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 Image

    https://hub.docker.com/r/greetoz/npm-ntlm I wouldn't trust your shortened image name for pulling the right one :-)

  21. azaloum90 commented on Sep 17, 2025

    @azaloum90
    Author
  22. azaloum90 commented on Oct 14, 2025

    @azaloum90
    Author

    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
    …

    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

    # Uncomment the next line if you uncomment anything in the section
    # environment:
      # Uncomment this if you want to change the location of
      # the SQLite DB file within the container
      # DB_SQLITE_FILE: "/data/database.sqlite"
    
      # Uncomment this if IPv6 is not enabled on your host
      # DISABLE_IPV6: 'true'
    
    volumes:
      - /mnt/docker/npm/data:/data
      - /mnt/docker/npm/letsencrypt:/etc/letsencrypt
    

    `

    I am getting this error in the logs:

    nginx: [emerg] unknown directive "ntlm" in /data/nginx/custom/http_top.conf:4

    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?

  23. trentsteenholdt-synergyau commented on Oct 14, 2025

    @trentsteenholdt-synergyau

    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
    …

    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

    # Uncomment the next line if you uncomment anything in the section
    # environment:
      # Uncomment this if you want to change the location of
      # the SQLite DB file within the container
      # DB_SQLITE_FILE: "/data/database.sqlite"
    
      # Uncomment this if IPv6 is not enabled on your host
      # DISABLE_IPV6: 'true'
    
    volumes:
      - /mnt/docker/npm/data:/data
      - /mnt/docker/npm/letsencrypt:/etc/letsencrypt
    

    `

    I am getting this error in the logs:

    nginx: [emerg] unknown directive "ntlm" in /data/nginx/custom/http_top.conf:4

    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?

    Asking the real basic question, but are you sure your docker image has been composed with the right image? E.g. docker-compose up -d

    Also it could just be the formatting, but make sure your compose file is formatted exactly with the right indents etc.

    Here is mine

    version: "3"
    services:
      app:
        image: 'greetoz/npm-ntlm:latest'
        restart: unless-stopped
        ports:
          # These ports are in format <host-port>:<container-port>
          - '80:80' # Public HTTP Port
          - '443:443' # Public HTTPS Port
          - '81:81' # Admin Web Port
          # Add any other Stream port you want to expose
          # - '21:21' # FTP
    
        # Uncomment the next line if you uncomment anything in the section
        # environment:
          # Uncomment this if you want to change the location of
          # the SQLite DB file within the container
          # DB_SQLITE_FILE: "/data/database.sqlite"
    
          # Uncomment this if IPv6 is not enabled on your host
          # DISABLE_IPV6: 'true'
    
        volumes:
          - ./data:/data
          - ./letsencrypt:/etc/letsencrypt
          - ./nginx-mods/20-dynamic-mods.conf:/etc/nginx/modules/20-dynamic-mods.conf:ro
    

    Might be the missing piece is the dynamic-mods reference.

    /opt/nginxproxymanager/nginx-mods
    root@cortana-rp01:/opt/nginxproxymanager/nginx-mods# cat 20-dynamic-mods.conf
    load_module /usr/lib/nginx/modules/ngx_http_upstream_ntlm_module.so;
    load_module /usr/lib/nginx/modules/ngx_http_geoip2_module.so;
    # load_module /usr/lib/nginx/modules/ngx_stream_geoip2_module.so;
    root@cortana-rp01:/opt/nginxproxymanager/nginx-mods#
  24. azaloum90 commented on Oct 25, 2025

    @azaloum90
    Author

    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
    …

    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

    # Uncomment the next line if you uncomment anything in the section
    # environment:
      # Uncomment this if you want to change the location of
      # the SQLite DB file within the container
      # DB_SQLITE_FILE: "/data/database.sqlite"
    
      # Uncomment this if IPv6 is not enabled on your host
      # DISABLE_IPV6: 'true'
    
    volumes:
      - /mnt/docker/npm/data:/data
      - /mnt/docker/npm/letsencrypt:/etc/letsencrypt
    

    `
    I am getting this error in the logs:

    nginx: [emerg] unknown directive "ntlm" in /data/nginx/custom/http_top.conf:4

    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?

    Asking the real basic question, but are you sure your docker image has been composed with the right image? E.g. docker-compose up -d

    Also it could just be the formatting, but make sure your compose file is formatted exactly with the right indents etc.

    Here is mine

    version: "3"
    services:
    app:
    image: 'greetoz/npm-ntlm:latest'
    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
    # - '21:21' # FTP

    # Uncomment the next line if you uncomment anything in the section
    # environment:
      # Uncomment this if you want to change the location of
      # the SQLite DB file within the container
      # DB_SQLITE_FILE: "/data/database.sqlite"
    
      # Uncomment this if IPv6 is not enabled on your host
      # DISABLE_IPV6: 'true'
    
    volumes:
      - ./data:/data
      - ./letsencrypt:/etc/letsencrypt
      - ./nginx-mods/20-dynamic-mods.conf:/etc/nginx/modules/20-dynamic-mods.conf:ro
    

    Might be the missing piece is the dynamic-mods reference.

    /opt/nginxproxymanager/nginx-mods
    root@cortana-rp01:/opt/nginxproxymanager/nginx-mods# cat 20-dynamic-mods.conf
    load_module /usr/lib/nginx/modules/ngx_http_upstream_ntlm_module.so;
    load_module /usr/lib/nginx/modules/ngx_http_geoip2_module.so;

    load_module /usr/lib/nginx/modules/ngx_stream_geoip2_module.so;

    root@cortana-rp01:/opt/nginxproxymanager/nginx-mods#

    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:4

    Other 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,

  25. azaloum90 commented on Nov 8, 2025

    @azaloum90
    Author

    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
    …

    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

    # Uncomment the next line if you uncomment anything in the section
    # environment:
      # Uncomment this if you want to change the location of
      # the SQLite DB file within the container
      # DB_SQLITE_FILE: "/data/database.sqlite"
    
      # Uncomment this if IPv6 is not enabled on your host
      # DISABLE_IPV6: 'true'
    
    volumes:
      - /mnt/docker/npm/data:/data
      - /mnt/docker/npm/letsencrypt:/etc/letsencrypt
    

    `
    I am getting this error in the logs:

    nginx: [emerg] unknown directive "ntlm" in /data/nginx/custom/http_top.conf:4

    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?

    Asking the real basic question, but are you sure your docker image has been composed with the right image? E.g. docker-compose up -d

    Also it could just be the formatting, but make sure your compose file is formatted exactly with the right indents etc.

    Here is mine

    version: "3"
    services:
    app:
    image: 'greetoz/npm-ntlm:latest'
    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
    # - '21:21' # FTP

    # Uncomment the next line if you uncomment anything in the section
    # environment:
      # Uncomment this if you want to change the location of
      # the SQLite DB file within the container
      # DB_SQLITE_FILE: "/data/database.sqlite"
    
      # Uncomment this if IPv6 is not enabled on your host
      # DISABLE_IPV6: 'true'
    
    volumes:
      - ./data:/data
      - ./letsencrypt:/etc/letsencrypt
      - ./nginx-mods/20-dynamic-mods.conf:/etc/nginx/modules/20-dynamic-mods.conf:ro
    

    Might be the missing piece is the dynamic-mods reference.

    /opt/nginxproxymanager/nginx-mods
    root@cortana-rp01:/opt/nginxproxymanager/nginx-mods# cat 20-dynamic-mods.conf
    load_module /usr/lib/nginx/modules/ngx_http_upstream_ntlm_module.so;
    load_module /usr/lib/nginx/modules/ngx_http_geoip2_module.so;

    load_module /usr/lib/nginx/modules/ngx_stream_geoip2_module.so;

    root@cortana-rp01:/opt/nginxproxymanager/nginx-mods#

    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

  26. github-actions commented on May 29, 2026

    @github-actions

    Issue is now considered stale. If you want to keep it open, please comment 👍

Sign up for free to join this conversation on GitHub. Already have an account? Sign in to comment

Metadata

Metadata

Assignees

No one assigned

    Labels

    Type

    No type

    Projects

    No projects

      Milestone

      No milestone

      Relationships

      None yet

      Development

      No branches or pull requests

      Issue actions