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my message can sometimes not be delivered because of an incorrect alias. Sometimes it works. 1 Recommended Answer 786 Replies 1738 Upvotes
hello,
Sometimes (!) I am getting a message that my email could not be delivered because the credentials of the alias I am sending are not correct or are outdated. But this happens with 1 out of 10 messages and randomly with the people I am sending this to. One minute later with another new message it then works again. I use gmail in the browser to send my emails.
Any one any idea?
thanks
Marjon
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As many of you have discovered, the problem is, primarily, with the certificates on the SMTP servers, but was only revealed when Google started stricter enforcement.
AFAICT, it looks like there are two main problems, self-signed certificates and certificates that do not match the domain name used in the custom SMTP settings.
- If you manage your own SMTP servers, you will need to get a certificate signed by a recognised CA, and identify it with the domain name you use in your SMTP configuration.
- If you get your service from a major email provider, they will not be using self-signed certificates, but they may be sharing the server between many customers, allowing each customer to use a custom domain name pointing to the same machine. The solution for that is to get the canonical name from the provider to use in your SMTP settings.
- It is rare, but it is possible that the server will use a different certificate on different ports, so switching between 465, 587 and 25 might yield better results. Again, the best source for the settings is your email provider.
I do not recommend using a non-secure connection to send your mail.
Google have updated the help article for Send emails from a different address or alias to include a section about this problem. It basically reiterates what you all have discovered in this thread:
If you see one of these error messages, you might need to select a different port number and authentication type. Make sure you have used the correct outgoing mail server for your provider. You might need to contact your third party email provider for the correct settings.
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I forgot the message I am seeing is also saying:
De reactie was:
TLS Negotiation failed, the certificate doesn't match the host.
I am getting this, although nothing changed since 4 days with some emails.
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Same issue here. Out of 10 messages to the same email address... 1 or 2 may come back with a TLS error.
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Same issue here. Just started happening to me very intermittently. Looks like a Google-wide issue that has absolutely nothing to do with the 3rd party servers?? Google please confirm and FIX. Thanks
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I have been having the same problem for about a week to a week and a half.
I also see exactly what the posters say -- it is inconsistent, clearly some Gmail systems are configured differently than others, and it's random as to which one attempts to connect, because some of them are fine with my configuration and others are not.
The maddening thing is that the TLS certificate I'm using absolutely matches the host!
It is a self signed certificate but that's never been a problem in the past.
syd-barrett.accessgroupinc.com
No affiliation but I used
the detailed results from this site indicate no problems except for self signed certificate
Note that the server identifies itself as syd-barrett.accessgroupinc.com AND the reverse DNS resolves to syd-barrett.accessgroupinc.com AND the MX records all use syd-barrett.accessgroupinc.com
I am therefore baffled, which is unusual... I have 30+ years experience with system administration and used to hack Sendmail back in the day... contributed a tiny bit to Postfix years and years ago...
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I had the problem. Solved it permanently.
It's a SSL/TLS certification issue.
a. make sure your domain has it
b. make sure your mail related subdomains has it
c. worst-case scenario, add a wildcard certificate to the domain
d. make sure related cloudflare/cdn settings are made are created (I had to create a TXT record)
My workplace's webhost had separate components for the certifying a domain, which explains b and c.
Slightly more detailed walkthrough here.
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