skysgroupsales6684's profile

3 Messages

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166 Points

Tue, May 17, 2022 9:41 PM

License Certificate EXPIRED!

WHY IS THIS ALWAYS HAPPENING WITH HOMESTEAD?  We use third-party sites to work and sent out communications with platforms and this is more of a headache than my actual job.  Then, we call the new employees/freelancers at homestead act as if they know nothing of the such!  Help, please Help!  We were told to send screenshots of how we set up our accounts on all third-party sites (yikes, what) or we can take our business to another email provider!  Wow out of 7 years doing business with HOMESTEAD we have NEVER been told to do such a thing.

48 Messages

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724 Points

1 m ago

My experience--on my iPad, iPhone, and iMac--has been that, if my email accounts were configured with Port 587 for the Outgoing Mail Server (SMTP), then I would get a "Not Trusted" error when trying to send email, and the details on the error would point to an expired certificate that expired May 14, 2022 at 7:00 pm.  No amount of restarts of the email apps or the devices resolved the problem on any of the three devices.

However, if I changed the Port to 465 in the configuration for each email account, I no longer got the "Not Trusted" error on any of the three devices for both of my email accounts.

So, my uneducated guess is that Homestead is still providing its old, expired certificate when we attempt to send mail using Port 587, but is providing the new, renewed certificate when we send mail using Port 465.

Brand User

5.2K Messages

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94.2K Points

1 m ago

Hello, 

Our certificate is and has been current. It expired and was renewed with no downtime. What's happening is that some email clients are not refreshing the certificate or it's caching. Unfortunately, we have no control over this. We can only suggest troubleshooting steps like restarting your email application, restarting your entire device, or re-entering the email client settings that we provide (that do suggest first that you use port 465, like TechWtr says), which all help refresh or clear caching.
These steps have successfully resolved this issue for everyone that I've talked to. 

48 Messages

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724 Points

@elyzabethv​ 

I know Port 465 is Homestead's suggested port for the Outgoing Mail Server (SMTP).  I was using Port 587 instead of 465 on three of our devices at Homestead Support's suggestion many months ago when we suddenly started having email issues.  (I can no longer recall the problem we were having.)  Starting Saturday evening, May 14, we started getting the "Not Trusted" error due to a certificate expiring on May 14 at 7:00 pm on two email accounts on all three devices configured with Port 587.  On our two other devices configured with a third email account using Port 465, the error did not occur.

Because of this experience, because the problem disappeared when the Port was changed back from 587 to 465, because Apple Support insisted they do NOT cache SSL email certificates on the iPad and iPhone, but do save an expired certificate to Keychain Access IF the user overrides security and accepts the expired certificate, and because some other users have reported this same problem, I think it is worth checking whether Homestead is providing its old, expired certificate in the case when customers use Port 587.

Brand User

5.2K Messages

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94.2K Points

I'm sorry, but we can't provide proper certificate credentials on one port and not another. What's happening is changing the settings is helping to clear whatever caching is causing this issue. I'm glad your emails are working now. 

48 Messages

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724 Points

@elyzabethv​ 

Well, Apple Support says the iPad, iPhone, and iMac do NOT cache email certificates.  And you are saying that 3 of our devices using outgoing SMTP Port 587 somehow cached the old expired certificate while 2 of our devices using outgoing SMTP Port 465 did NOT.  As a test, I tried to change the outgoing SMTP port back to Port 587 on my iPad,  but the configuration change failed with the same May 14 expired certificate.

Brand User

5.2K Messages

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94.2K Points

I'm sorry, but I'm not sure what answer I can give you here. I just tested using port 587 on my Outlook that I have my Homestead email connected to and didn't experience any issues. This is not an issue coming from Homestead.