Hotmail/Free Outlook accounts #301

ExolonDX · 2024-10-22T00:09:58Z

ExolonDX
Oct 22, 2024

Hi Simon,

First thanks for writing this proxy server, both my spam filter and pop checker are working.

I just saw your update regarding Hotmail/Free Outlook accounts; I was trying to use the Azure Portal website to set everything up, although everything appeared to be OK, I kept on getting authentication errors.

Just about to give when I came across another proxy server, Raiden Mail Oauth Proxy. On Raidens website it gave instructions on how to setup client_id/client_secret but using the Microsoft Entra website, not the Azure Portal website.

However, this gave me the following error:

2024-10-20 22:56:08,123: Authorisation request received for xxxxxxxxxx@outlook.com (interactive mode)
2024-10-20 22:56:17,170: Returning authorisation request result for xxxxxxxxxx@outlook.com
2024-10-20 22:56:17,172: Authorisation result error for account xxxxxxxxxx@outlook.com - aborting login. OAuth 2.0 authorisation error for account xxxxxxxxxx@outlook.com: invalid_request; The request is not valid for the application's 'userAudience' configuration. In order to use /common/ endpoint, the application must not be configured with 'Consumer' as the user audience. The userAudience should be configured with 'All' to use /common/ endpoint.
2024-10-20 22:56:17,174: POP (127.0.0.1:54802-{127.0.0.1:3995}-outlook.office365.com:995)     --> b'*\r\n'
2024-10-20 22:56:17,192: POP (127.0.0.1:54802-{127.0.0.1:3995}-outlook.office365.com:995)     <-- b'-ERR The AUTH protocol exchange was canceled by the client.\r\n'
2024-10-20 22:56:17,193: POP (127.0.0.1:54802-{127.0.0.1:3995}-outlook.office365.com:995) <-- b"-ERR Authentication failed. Email OAuth 2.0 Proxy: Login failed for account xxxxxxxxxx@outlook.com: OAuth 2.0 authorisation error for account xxxxxxxxxx@outlook.com: invalid_request; The request is not valid for the application's 'userAudience' configuration. In order to use /common/ endpoint, the application must not be configured with 'Consumer' as the user audience. The userAudience should be configured with 'All' to use /common/ endpoint.\r\n"
2024-10-20 22:56:17,205: POP (127.0.0.1:54802-{127.0.0.1:3995}-outlook.office365.com:995) --> b'QUIT\r\n'

A quick Google search and the suggestions were to edit the Manifest and change the "signInAudience" from "PersonalMicrosoftAccount" to "AzureADandPersonalMicrosoftAccount", then everything authenticated successfully:

2024-10-20 23:03:05,508: Accepting new connection from 127.0.0.1:54998 to POP server at 127.0.0.1:3995 (unsecured) proxying outlook.office365.com:995 (SSL/TLS)
2024-10-20 23:03:05,508: Ignoring incoming connection to POP server at 127.0.0.1:3995 (unsecured) proxying outlook.office365.com:995 (SSL/TLS) - no connection information
2024-10-20 23:03:05,615: POP (127.0.0.1:54998-{127.0.0.1:3995}-outlook.office365.com:995) --> [ Client connected ]
2024-10-20 23:03:05,615: POP (127.0.0.1:54998-{127.0.0.1:3995}-outlook.office365.com:995) <-> [ Starting TLS handshake ]
2024-10-20 23:03:06,041: POP (127.0.0.1:54998-{127.0.0.1:3995}-outlook.office365.com:995) <-> [ TLSv1.2 handshake complete ]
2024-10-20 23:03:06,043: POP (127.0.0.1:54998-{127.0.0.1:3995}-outlook.office365.com:995)     <-- b'+OK The Microsoft Exchange POP3 service is ready. [TABPADQAUAAyADYANQBDAEEAMAAwADcANAAuAEcAQgBSAFAAMgA2ADUALgBQAFIATwBEAC4ATwBVAFQATABPAE8ASwAuAEMATwBNAA==]\r\n'
2024-10-20 23:03:06,043: POP (127.0.0.1:54998-{127.0.0.1:3995}-outlook.office365.com:995) <-- b'+OK The Microsoft Exchange POP3 service is ready. [TABPADQAUAAyADYANQBDAEEAMAAwADcANAAuAEcAQgBSAFAAMgA2ADUALgBQAFIATwBEAC4ATwBVAFQATABPAE8ASwAuAEMATwBNAA==]\r\n'
2024-10-20 23:03:06,046: POP (127.0.0.1:54998-{127.0.0.1:3995}-outlook.office365.com:995) --> b'USER xxxxxxxxxx@outlook.com\r\n'
2024-10-20 23:03:06,046: POP (127.0.0.1:54998-{127.0.0.1:3995}-outlook.office365.com:995) <-- b'+OK\r\n'
2024-10-20 23:03:06,062: POP (127.0.0.1:54998-{127.0.0.1:3995}-outlook.office365.com:995) --> b'PASS [[ Credentials removed from proxy log ]]\r\n'
2024-10-20 23:03:06,062: POP (127.0.0.1:54998-{127.0.0.1:3995}-outlook.office365.com:995)     --> b'AUTH XOAUTH2\r\n'
2024-10-20 23:03:06,077: POP (127.0.0.1:54998-{127.0.0.1:3995}-outlook.office365.com:995)     <-- b'+ \r\n'
2024-10-20 23:03:07,025: POP (127.0.0.1:54998-{127.0.0.1:3995}-outlook.office365.com:995)     --> b'[[ Credentials removed from proxy log ]]\r\n'
2024-10-20 23:03:07,698: POP (127.0.0.1:54998-{127.0.0.1:3995}-outlook.office365.com:995; xxxxxxxxxx@outlook.com)     <-- b'+OK User successfully authenticated.\r\n'
2024-10-20 23:03:07,698: POP (127.0.0.1:54998-{127.0.0.1:3995}-outlook.office365.com:995; xxxxxxxxxx@outlook.com) [ Successfully authenticated POP connection - releasing session ]
2024-10-20 23:03:07,698: POP (127.0.0.1:54998-{127.0.0.1:3995}-outlook.office365.com:995; xxxxxxxxxx@outlook.com) <-- b'+OK User successfully authenticated.\r\n'
2024-10-20 23:03:07,701: POP (127.0.0.1:54998-{127.0.0.1:3995}-outlook.office365.com:995; xxxxxxxxxx@outlook.com) --> b'STAT\r\n'
2024-10-20 23:03:07,810: POP (127.0.0.1:54998-{127.0.0.1:3995}-outlook.office365.com:995; xxxxxxxxxx@outlook.com) <-- b'+OK 2 212965\r\n'
2024-10-20 23:03:07,812: POP (127.0.0.1:54998-{127.0.0.1:3995}-outlook.office365.com:995; xxxxxxxxxx@outlook.com) --> b'LIST\r\n'
2024-10-20 23:03:07,895: POP (127.0.0.1:54998-{127.0.0.1:3995}-outlook.office365.com:995; xxxxxxxxxx@outlook.com) <-- b'+OK 2 212965\r\n1 133774\r\n2 79191\r\n.\r\n'
2024-10-20 23:03:07,899: POP (127.0.0.1:54998-{127.0.0.1:3995}-outlook.office365.com:995; xxxxxxxxxx@outlook.com) --> b'UIDL\r\n'
2024-10-20 23:03:07,964: POP (127.0.0.1:54998-{127.0.0.1:3995}-outlook.office365.com:995; xxxxxxxxxx@outlook.com) <-- b'+OK\r\n1 7425\r\n2 7429\r\n.\r\n'
2024-10-20 23:03:07,967: POP (127.0.0.1:54998-{127.0.0.1:3995}-outlook.office365.com:995; xxxxxxxxxx@outlook.com) --> b'RETR 1\r\n'
2024-10-20 23:03:08,116: POP (127.0.0.1:54998-{127.0.0.1:3995}-outlook.office365.com:995; xxxxxxxxxx@outlook.com) <-- b'+OK\r\n'
2024-10-20 23:03:08,250: POP (127.0.0.1:54998-{127.0.0.1:3995}-outlook.office365.com:995; xxxxxxxxxx@outlook.com) --> b'DELE 1\r\n'
2024-10-20 23:03:08,305: POP (127.0.0.1:54998-{127.0.0.1:3995}-outlook.office365.com:995; xxxxxxxxxx@outlook.com) <-- b'+OK\r\n'
2024-10-20 23:03:08,307: POP (127.0.0.1:54998-{127.0.0.1:3995}-outlook.office365.com:995; xxxxxxxxxx@outlook.com) --> b'RETR 2\r\n'
2024-10-20 23:03:08,425: POP (127.0.0.1:54998-{127.0.0.1:3995}-outlook.office365.com:995; xxxxxxxxxx@outlook.com) <-- b'+OK\r\n'
2024-10-20 23:03:08,462: POP (127.0.0.1:54998-{127.0.0.1:3995}-outlook.office365.com:995; xxxxxxxxxx@outlook.com) --> b'DELE 2\r\n'
2024-10-20 23:03:08,507: POP (127.0.0.1:54998-{127.0.0.1:3995}-outlook.office365.com:995; xxxxxxxxxx@outlook.com) <-- b'+OK\r\n'
2024-10-20 23:03:08,514: POP (127.0.0.1:54998-{127.0.0.1:3995}-outlook.office365.com:995; xxxxxxxxxx@outlook.com) --> b'QUIT\r\n'
2024-10-20 23:03:09,271: POP (127.0.0.1:54998-{127.0.0.1:3995}-outlook.office365.com:995; xxxxxxxxxx@outlook.com) <-- b'+OK Microsoft Exchange Server POP3 server signing off.\r\n'
2024-10-20 23:03:09,275: POP (127.0.0.1:54998-{127.0.0.1:3995}-outlook.office365.com:995; xxxxxxxxxx@outlook.com) --> [ Client disconnected ]
2024-10-20 23:03:09,278: POP (127.0.0.1:54998-{127.0.0.1:3995}-outlook.office365.com:995) <-- [ Server disconnected ]

So instead of trying to use another applications client_id which has the potential to change and cause problems, you can create your own using Microsofts Entra website.

Colin.

simonrob · 2024-11-06T20:34:08Z

simonrob
Nov 6, 2024
Maintainer

Thanks for this very useful insight! This is something I've never tried myself (I don't use the free version of these services), and based solely on others' reported experiences had always thought that it wasn't supported But it seems like this was a mistaken assumption, and as long as you have a M365 Developer or Azure account this is in fact possible.

I just tried this myself with a Hotmail account, and was able to get it working very easily. After clicking the button to create a new app registration from the Entra admin centre, these were the only steps I needed:

On the app registration page, enter any display name of your choice, and for the supported account types option, select "Accounts in any organizational directory (Any Microsoft Entra ID tenant - Multitenant) and personal Microsoft accounts (e.g. Skype, Xbox)". I ignored the optional redirect URI at this stage, and just clicked Register.
Once the application is created, copy the Application (client) ID from the summary page that is displayed – this is required for the proxy's configuration file (see below).
In the Authentication tab, click the button to add a platform, and choose "Mobile and desktop applications". In the Custom redirect URIs box, enter http://localhost and press Configure.

The corresponding proxy configuration entry to support IMAP/POP/SMTP is:

[your.outlook.or.hotmail.email.address@hotmail.com]
permission_url = https://login.microsoftonline.com/common/oauth2/v2.0/authorize
token_url = https://login.microsoftonline.com/common/oauth2/v2.0/token
oauth2_scope = https://outlook.office.com/IMAP.AccessAsUser.All https://outlook.office.com/POP.AccessAsUser.All https://outlook.office.com/SMTP.Send offline_access
redirect_uri = http://localhost
client_id = *** your client ID from step 2 here ***

This was all that was required for me, and it worked first time with no issues. Considering this is so much easier than Google's version of the same process, I'm surprised it has caused as much trouble as it has. I will point to this discussion from the proxy's readme and configuration file, and hopefully this will help others navigate the process a little easier.

It's interesting to see Raiden's application. I haven't looked into whether it is just a paid-for wrapper around this proxy or a separate product, but the client setup documentation is perhaps useful nonetheless.

9 replies

Eds1989 Jan 5, 2025

Thanks for the confirmation.

I have several internal services and devices that I want to send messages from using my Outlook.com account, but they do no support OAuth, so that is why I have setup this tool.
I have been using my App password as I presumed that was a requirement, as it certainly was for devices/services that didn't support MFA using basic auth.

simonrob Jan 6, 2025
Maintainer

With the proxy there's no need for app passwords – you're authenticating using OAuth instead. The password you use when you log in to the proxy for the first time is used only between your email client(s) and the proxy itself. There's more detail here.

Eds1989 Jan 12, 2025

Understood, thank you for clarifying.

yusi1 Feb 11, 2025

Thanks for this very useful insight! This is something I've never tried myself (I don't use the free version of these services), and based solely on others' reported experiences had always thought that it wasn't supported But it seems like this was a mistaken assumption, and as long as you have a M365 Developer or Azure account this is in fact possible.

I just tried this myself with a Hotmail account, and was able to get it working very easily. After clicking the button to create a new app registration from the Entra admin centre, these were the only steps I needed:
1. On the app registration page, enter any display name of your choice, and for the supported account types option, select _"Accounts in any organizational directory (Any Microsoft Entra ID tenant - Multitenant) and personal Microsoft accounts (e.g. Skype, Xbox)"_. I ignored the optional redirect URI at this stage, and just clicked Register.

2. Once the application is created, copy the Application (client) ID from the summary page that is displayed – this is required for the proxy's configuration file (see below).

3. In the Authentication tab, click the button to add a platform, and choose _"Mobile and desktop applications"_. In the Custom redirect URIs box, enter `http://localhost` and press Configure.
The corresponding proxy configuration entry to support IMAP/POP/SMTP is:
[your.outlook.or.hotmail.email.address@hotmail.com]
permission_url = https://login.microsoftonline.com/common/oauth2/v2.0/authorize
token_url = https://login.microsoftonline.com/common/oauth2/v2.0/token
oauth2_scope = https://outlook.office.com/IMAP.AccessAsUser.All https://outlook.office.com/POP.AccessAsUser.All https://outlook.office.com/SMTP.Send offline_access
redirect_uri = http://localhost
client_id = *** your client ID from step 2 here ***
This was all that was required for me, and it worked first time with no issues. Considering this is so much easier than Google's version of the same process, I'm surprised it has caused as much trouble as it has. I will point to this discussion from the proxy's readme and configuration file, and hopefully this will help others navigate the process a little easier.

It's interesting to see Raiden's application. I haven't looked into whether it is just a paid-for wrapper around this proxy or a separate product, but the client setup documentation is perhaps useful nonetheless.

I recently tried to create a new application for email-oauth2-proxy but I am now met with this error:

The ability to create applications outside of a directory has been deprecated. You may get a new directory by [joining the M365 Developer Program](https://aka.ms/joinM365DeveloperProgram) or [signing up for Azure](https://aka.ms/signUpForAzure).

simonrob Feb 11, 2025
Maintainer

You missed a key part in the first paragraph: as long as you have a M365 Developer or Azure account this is in fact possible. Unfortunately there's nothing that can be done about this – you'll need to register for one of those accounts.

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