Encrypted error message on SMTP failed

Question

With one of our customers, we keep getting strangely coded error messages back from the smtp.office365.com server via SMTP 587/STARTTLS. The access data is correct and a test runs correctly. But reports kept popping up throughout the day. With other customers, same system, same configuration, everything runs perfectly.

                [error] => QUIT command failed
                [detail] => X�  T���!�t�a������e��¢��z��^�� ...
Kind regards,

Andreas

Answer 1

Dear OMOC.interactive Mause

Thanks a lot for your feedback!

According to your further information, please first kindly check whether this official document can help you Fix issues with printers, scanners, and LOB apps that send email using Microsoft 365 - Exchange | Microsoft Learn

Wish you have a wonderful day and always stay safe!

Sincerely

Kerry Chen | Microsoft Community Moderator

Answer 2

The problem now suddenly occurs with another customer. Here, however, with a concrete, readable error message:

"SMTP Error: Could not connect to SMTP host. Connection failed. stream_socket_enable_crypto(): SSL: Handshake timed out".

"SMTP Error: Could not connect to SMTP host. Connection failed. stream_socket_enable_crypto(): SSL: Handshake timed out".

2023-07-31 11:00:48 Connection: opened

2023-07-31 11:00:51 SERVER -> CLIENT: 220 FR3P281CA0119.outlook.office365.com Microsoft ESMTP MAIL Service ready at Mon, 31 Jul 2023 11:00:51 +0000

2023-07-31 11:00:51 CLIENT -> SERVER: EHLO domain.tld

2023-07-31 11:00:52 SERVER -> CLIENT: 250-FR3P281CA0119.outlook.office365.com Hello [2a01:4f8:171:16ed::2]250-SIZE 157286400250-PIPELINING250-DSN250-ENHANCEDSTATUSCODES250-STARTTLS250-8BITMIME250-BINARYMIME250-CHUNKING250 SMTPUTF8

2023-07-31 11:00:52 CLIENT -> SERVER: STARTTLS

2023-07-31 11:00:52 SERVER -> CLIENT: 220 2.0.0 SMTP server ready

2023-07-31 11:01:12 Connection failed. SMTP Error: Could not connect to SMTP host. Connection failed. stream_socket_enable_crypto(): SSL: Handshake timed out

2023-07-31 11:01:12 CLIENT -> SERVER: QUIT

Answer 3

Dear Kerry,

no, it is an SMTP service in our online software under PHP with PHPMailer.

I sent you a screenshot. More data if you like.

A heartfelt thank you!

Answer 4

Dear OMOC.interactive Mause

Good day! Thank you for publishing in Microsoft Community. We are happy to help you!

Based on your description, I have a general understanding of your problem, but in order to help you better, I still need to gather more information to narrow down the problem

• First of all, is the user in question using an Outlook desktop client or OWA (Outlook web app)? If you use Outlook Desktop Client, does using OWA have the same error?
• Other than that, the user seems to have received some error messages and error codes, but you don't seem to have provided me with a complete screenshot. I understand that you are worried about the risk of private information leakage, so please try to send me a complete screenshot in a private message, there is enough security and also for me to understand the problem further, thank you. For your reference: Please kindly click account you logged in on the up-right corner - My profile - View private messages to reply.

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