SMTP does not work

Anonymous
2023-01-09T19:05:01+00:00

Hi,

My Sage accounting system used to send invoices with no issues and then stopped working for a second time. The first time I had to change the configuration of the SMTP server which had fixed the issue for several months. Now it doesn't send emails again.

I have confirmed that the settings have not changed. The only security option is the torn on SSL/TLS or not with a check mark. The setting are as follows:

Why did it stop working (around end of Nov.) ?

Outlook | Windows | Classic Outlook for Windows | For business

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  1. Anonymous
    2023-01-10T14:39:26+00:00

    Consumer accounts did not disable basic auth (and have no plans to do so in the near future.)

    Are the messages being sent but not received or is Sage unable to send them?

    The first issue could be spam filters on the recipient side - recipients need to check the junk mail folder in their mailbox. It's also possible that Microsoft filtered it as junk - this is more likely if you send a lot at once.

    What OS are you using? Is Sage installed and sending from your computer? They also disabled TLS1.1 and 1.0 around the time it stopped working - but it only affects Windows 7 (and older). If you are using a cloud-based version, this would not apply.

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  2. Anonymous
    2023-01-10T14:45:25+00:00

    One thing I just noticed is that every suggestion I received seems to ignore that this used to work perfectly for weeks and it stopped working with no change on my side. Something changed on the outlook side or windows side to make it stop working. with no tools to try to see if there are errors, it is very hard to fix.

    I'm going to try to find a tool of some kind to send test emails and see if there are error messages of any kind.

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  3. Anonymous
    2023-01-10T14:52:55+00:00

    I see the emails in the sent folder.

    I sent some to my own accounts (hotmail, gmail & bellnet) and I received none of them. I know all of the settings of all 3 accounts very well. not in the junk folders at all. This is how I tested in the past successfully.

    I use Windows10 and PC based Sage. I usually send 1 at a time.

    If Microsoft marked it as junk, it should show in the junk folder right ?

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  4. Anonymous
    2023-01-10T15:20:11+00:00

    I have not tested this but I see that the server name you are using for SMTP is different than the one listed here, POP, IMAP, and SMTP settings for Outlook.com - Microsoft Support. This page says it should be smtp-mail.outlook.com. Something to try.

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  5. Anonymous
    2023-01-10T15:23:07+00:00

    Wormly has a SMTP tester and it fails here is the results:

    Starting SMTP test of: smtp.office365.com 0.00s
    Resolved IP address to: 40.97.188.242
    Connection: opening to 40.97.188.242:587, timeout=15
    Connection: opened 0.01s
    < 220 BL0PR0102CA0031.outlook.office365.com Microsoft ESMTP MAIL Service ready at Tue, 10 Jan 2023 15:20:56 +0000 0.11s
    SMTP connection established
    > EHLO www.wormly.com
    < 250-BL0PR0102CA0031.outlook.office365.com Hello [172.104.20.135] 250-SIZE 157286400 250-PIPELINING 250-DSN 250-ENHANCEDSTATUSCODES 250-STARTTLS 250-8BITMIME 250-BINARYMIME 250-CHUNKING 250 SMTPUTF8 0.21s
    > MAIL FROM:<******@wormly.com> 0.21s
    < 451 5.7.3 STARTTLS is required to send mail [BL0PR0102CA0031.prod.exchangelabs.com] 5.21s
    SMTP ERROR: MAIL FROM command failed: 451 5.7.3 STARTTLS is required to send mail [BL0PR0102CA0031.prod.exchangelabs.com]
    > RCPT TO:<s****@*****.**m>
    <
    SMTP ERROR: RCPT TO command failed:
    SMTP Error: RCPT TO command failed

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