1 Topic by HeuvelTop

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Topic: Outlook Office 2021 not signing in

Goodmorning!

My Iredmail is on Ubuntu 22.04 with nginx, from downloadable installer:
iRedMail     1.6.1
iRedAdmin-Pro     5.3 (PostgreSQL)

My customer has decided to start using Office 2021 Outlook. But I can't get Outlook to verify the account with the iRedmail server.

When I try the WIn10 based mail config I keep receiving  unknown errorcode: 0x8004011c.

No matter if I use SSL/TLS or STARTTLS for the IMAP connection.

This is the related part of mail.log:

Jan 13 07:56:02 mail postfix/submission/smtpd[44848]: Anonymous TLS connection established from unknown[192.168.4.119]: TLSv1.2 with cipher ECDHE-RSA-AES256-GCM-SHA384 (256/256 bits)
Jan 13 07:56:02 mail postfix/submission/smtpd[44848]: NOQUEUE: reject: RCPT from unknown[192.168.4.119]: 554 5.7.1 <unknown[192.168.4.119]>: Client host rejected: Access denied; from=<xxxxx@vd-hoven.nl> to=<xxxxx@vd-hoven.nl> proto=ESMTP helo=<PCmaarten>
Jan 13 07:56:02 mail postfix/submission/smtpd[44848]: warning: TLS library problem: error:0A000126:SSL routines::unexpected eof while reading:../ssl/record/rec_layer_s3.c:308:
Jan 13 07:56:02 mail postfix/submission/smtpd[44848]: lost connection after RCPT from unknown[192.168.4.119]
Jan 13 07:56:02 mail postfix/submission/smtpd[44848]: disconnect from unknown[192.168.4.119] helo=1 ehlo=1 starttls=1 mail=1 rcpt=0/1 commands=4/5

Is it related to the TLS warning?

I don't see any Dovecot errors. The Outlook test-email does get delivered.

----

Spider Email Archiver: On-Premises, lightweight email archiving software developed by iRedMail team. Supports Amazon S3 compatible storage and custom branding.

2 Reply by ZhangHuangbin

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Re: Outlook Office 2021 not signing in

HeuvelTop wrote:

Jan 13 07:56:02 mail postfix/submission/smtpd[44848]: NOQUEUE: reject: RCPT from unknown[192.168.4.119]: 554 5.7.1 <unknown[192.168.4.119]>: Client host rejected: Access denied; from=<xxxxx@vd-hoven.nl> to=<xxxxx@vd-hoven.nl> proto=ESMTP helo=<PCmaarten>

- Do you have SMTP AUTH enabled in Outlook?
- Please also show us command output:

postconf -Mf submission

3 Reply by HeuvelTop

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Re: Outlook Office 2021 not signing in

- Do you have SMTP AUTH enabled in Outlook?
No!

- output:

root@mail:~# postconf -Mf submission
submission inet  n       -       n       -       -       smtpd
    -o syslog_name=postfix/submission
    -o smtpd_tls_security_level=encrypt
    -o smtpd_sasl_auth_enable=yes
    -o smtpd_client_restrictions=permit_sasl_authenticated,reject
    -o content_filter=smtp-amavis:[127.0.0.1]:10026

4 Reply by HeuvelTop

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Re: Outlook Office 2021 not signing in

After a few days of searching, I have found this is not an iRedmail, Postfix or Dovecot problem.

It turned out Outlook 2021 does work on most Win 10 desktops. Only some won't connect with IMAP server because of the 0x8004011c error.

I have searched the Internet and tried several MS fixes. I am not allowed to post URL's here. This fixed the 0x8004011c error on one of 2 PC's:

[HKEY_LOCAL_MACHINE\SOFTWARE\Microsoft\Cryptography\Protect\Providers\df9d8cd0-1501-11d1-8c7a-00c04fc297eb]
-> Add this key    "ProtectionPolicy"=dword:00000001

I found the solution on  Spiceworks, topic: 1632816.

On the other PC it was solved by creating a whole new profile for that user.

5 Reply by HeuvelTop (edited by HeuvelTop 2023-01-18 18:36:09)

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Re: Outlook Office 2021 not signing in

The config that works is:
- IMAP with STARTTLS on port 143
- SMTP with STARTTLS on port 587
- no encrypted authentication