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a message that my email could not be delivered because the credentials of the alias I am sending are not correct or are outdated.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.
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.
Check with your other mail service for their recommended port number, authentication type, or outgoing mail server. Make sure your third party provider supports SSL or TLS with a valid certificate.
Here are some common combinations:
Our automated system analyzes replies to choose the one that's most likely to answer the question. If it seems to be helpful, we may eventually mark it as a Recommended Answer.
-171
Relevant Answer Relevant Answers (0)
Our automated system analyzes the replies to choose the one that's most likely to answer the question.
Our automated system analyzes replies to choose the one that's most likely to answer the question. If it seems to be helpful, we may eventually mark it as a Recommended Answer.
Our automated system analyzes replies to choose the one that's most likely to answer the question. If it seems to be helpful, we may eventually mark it as a Recommended Answer.
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
Our automated system analyzes replies to choose the one that's most likely to answer the question. If it seems to be helpful, we may eventually mark it as a Recommended Answer.
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.
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...
Our automated system analyzes replies to choose the one that's most likely to answer the question. If it seems to be helpful, we may eventually mark it as a Recommended Answer.
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.
Our automated system analyzes replies to choose the one that's most likely to answer the question. If it seems to be helpful, we may eventually mark it as a Recommended Answer.
This question is locked and replying has been disabled.
Discard post? You will lose what you have written so far.
false
false
Subscribe to updates
Write a reply
10 characters required
Failed to attach file, click here to try again.
Edit link
Text to display:Link to:
–|
Notifications are currently off and you won't receive updates. To turn them on, go to Notifications preferences on your Profile page.
Discard post?
You will lose what you have written so far.
Personal information found
We found the following personal information in your message:
This information will be visible to anyone who visits or subscribes to notifications for this post. Are you sure you want to continue?
A problem occurred. Please try again.
Create Reply
Edit Reply
Link to post
Delete post?
This will remove the reply from the Answers section.
Notifications are off
Your notifications are currently off and you won't receive subscription updates. To turn them on, go to Notifications preferences on your Profile page.
Report abuse
Google takes abuse of its services very seriously. We're committed to dealing with such abuse according to the laws in your country of residence. When you submit a report, we'll investigate it and take the appropriate action. We'll get back to you only if we require additional details or have more information to share.
Go to the Legal Help page to request content changes for legal reasons.
Reported post for abuse
Unable to send report.
Report post
What type of post are you reporting?
Off-topic
Post is disrespectful, about third party products or contains unrelated content or personal information.
Abuse
Post contains harassment, hate speech, impersonation, nudity; malicious, illegal, sexually explicit or commercial content.
Google takes abuse of its services very seriously. We're committed to dealing with such abuse according to the laws in your country of residence. When you submit a report, we'll investigate it and take the appropriate action. We'll get back to you only if we require additional details or have more information to share.
Go to the Legal Help page to request content changes for legal reasons.
Reported post for abuse
Unable to send report.
Google user
This reply is no longer available.
Badges
Some community members might have badges that indicate their identity or level of participation in a community.
Google Employee — Google product team members and community managers
Community Specialist — Google partners who help ensure the quality of community content
Diamond Product Expert — Community members with product mastery who help other Google users and Product Experts
Platinum Product Expert — Community members with advanced product knowledge who help other Google users and Product Experts
Gold Product Expert — Community members with in-depth product knowledge who help other Google users by answering questions
Silver Product Expert — Community members with intermediate product knowledge who help other Google users by answering questions
Product Expert Alumni — Former Product Experts who are no longer members of the program
Community content may not be verified or up-to-date.
/mail/threads
//accounts.google.com/ServiceLogin
You'll receive email notifications for new posts at
Unable to delete question.
Unable to update vote.
Unable to update subscription.
You have been unsubscribed
Deleted
Unable to delete reply.
Removed from Answers
Marked as Recommended Answer
Removed recommendation
Undo
Unable to update reply.
Unable to update vote.
Thank you. Your response was recorded.
Unable to undo vote.
Thank you. This reply will now display in the answers section.