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8 Messages

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154 Points

Thu, May 26, 2022 1:30 AM

Certificate Expired

Is there an employee that can help resolve this issue?  Certificate expired 5/14/22.  Attempts to download certificate have failed (lack of instruction) and port 465 does not work.  Many people are having this issue.  Please help.  We have important business emails to send.

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Brand User

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Il y a 3 m

Hello, 

I'm sorry, but our email certificate is not and has not been expired. A few people experienced this same issue, but it ended up being caching through the email client. I would recommend you reset your email program or even your entire device. If you're still getting that error, please re-enter the correct email client settings:


‎Email Client Settings | Homestead Community

8 Messages

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154 Points

Il y a 3 m

Sorry, you might need to clarify.  Who is the email client?  How does one reset an email program?  Why would one need to re-enter email settings if they are already correct?  I am hoping for answers from Staff of Homestead.  Thank you.

Brand User

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The email client is whatever program you use to check your email. Closing the program completely and reopening it should work.

 

In the meantime, you can use Roundcube through your account to check your email. You'll find that, since our certificate is not actually expired, you won't receive this error when checking your mail directly through our system. 

49 Messages

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744 Points

@elyzabethv​ 

Well, it is not entirely accurate to say that your email certificate did not expire.  Homestead did at some point have a certificate that did indeed expire on May 14 (see attached image), or there would be no way for any of us customers to have obtained it and for our email apps to display it.

We encountered the expired certificate on three devices--our iPad, iPhone, and iMac--on two email accounts configured to use SMTP port 587 for outgoing email; we were only able to resolve it by changing the port back to 465 on all three devices for both accounts.  (We had changed the port from 465 to 587 at Homestead Support's oral advice at some point long ago when we suddenly had email issues on these three devices.)  On another iPhone and on a MacBook configured to access a third email account using SMTP port 465, we did NOT encounter the expired certificate.

Oh, and if I now try changing the SMTP port from 465 to 587 on any of our three devices, I will once again see the expired certificate.

I have contacted Apple Support.  They insist that no caching or saving of email certificates occurs on iPhones, iPads, or iMacs.

On the other hand, you (Homestead Support) say you never allowed the certificate to expire, and that you were not providing different certificates on ports 465 and 587, and in fact it was impossible to deliver an expired certificate on one port and a renewed certificate on another port.

I've spent hours searching the Internet for any logical explanation for what has happened here, and have been unable to do so.  There's very little  public information available on the mechanics of email certificates.

(edited)

1 Message

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150 Points

Thank you techwtr!! 587 to 465 [backwards of what we were told previously] worked like a charm!!

49 Messages

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744 Points

@elyzabethv​ 

I just tried an experiment. I went to our older Mac that we are no longer using, configured a fresh new email account on that Mac using one of our Homestead-hosted email addresses, and set it up with an outgoing SMTP port of 587 with "Use TLS/SSL" checked (the configuration I've used for years).  I then tried sending an email and it failed with the same expired certificate expiring May 14, 2022.

I then changed the SMTP port for that new email account on our old Mac to 465, and the send of the test email worked.

If Homestead has its new renewed certificate configured correctly on all SMTP ports on its server(s), then how in the world did this new email account on our old no-longer-used Mac obtain the expired certificate when using port 587?  The error showed the same expired certificate I included in my earlier post.

I respectfully suggest again that, when customers try to send email using SMTP port 587 on a Homestead-hosted email account, Homestead's email server(s) are providing the old email certificate that expired on May 14 at 7:00 pm.

Brand User

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The most accurate statement is that our certificate was renewed. The old certificate did expire, but a new certificate was applied. There was no gap in coverage on our end.

I have tested using port 587 on my end, and I've had a coworker test on 2 different devices on their end. We cannot replicate this issue. Now, we are using Windows computers, not Apple. I happen to know that another user that commented below with this issue also uses Apple products. If it were something on our end causing this, I would be able to replicate the issue. Nothing on our end would make this an Apple-specific issue. This means that somewhere in Apple's system, they are caching and still trying to use that old certificate. I know they say that this is not the case, but the evidence says otherwise. I wish it were something on our end because that would mean there was something we could do to fix it, but unfortunately, there is not. 

18 Messages

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514 Points

Il y a 3 m

I too seem to be getting this certificate expired message as well. So in the settings where it stares Post 587, I should just type 465 and that will fix things?

49 Messages

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744 Points

@tiffanyoga​ 

You change Port 587 for your outgoing SMTP Server with 465.  I have an iPhone, where it is called "Server Port".  On an Android phone I think it's just called "Port" under "outgoing server settings".  465 is what Homestead lists on their help page for email configurations; that page hasn't changed since 2019.

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514 Points

@techwtr​ That worked, thank you so much!

8 Messages

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154 Points

My email won't work using 465 outgoing with TLS; but it will using SSL.  Does this sound right?  IT is frustrating to not be able to reach out to Homestead.  Thank you

49 Messages

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744 Points

@connie5410​ 

I think Homestead Support needs to answer the TSL versus SSL question.  (They've been commenting on these threads.)  Homestead's "Email Client Settings" page dated June 2019 (https://community.homestead.com/conversations/email-support/email-client-settings/5f2a9b2d58180958845d23f0) says to use port 465 with "encryption/SSL" turned on, and if you have trouble receiving email, use port 587 with "encryption/SSL" turned off.

In iOS on an iPhone or iPad, the only option is "Use SSL".  On a Mac running Monterey, the only option is "Use TLS/SSL".  I've ALWAYS had them enabled on my iPhone, iPad, and iMac.  Many months ago, when we suddenly started having problems with email, at Homestead Support's oral suggestion I changed the port from 465 to 587 (but I kept SSL turned on).

After the certificate expired on May 14, I had to switch back to port 465 in order to continue sending email.

Brand User

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98.6K Points

If you look at the email client settings we provide, we suggest using Port 465 and SSL. It's only if you're experiencing issues that you should try other settings like 587. On some email clients, SSL might not work with 587, so you may need to switch it to TLS, but our suggested settings are the ones that are working for you.