@elyzabethv I have restarted Outlook 365 on my computer and run it on different browsers. I have updated and even changed the mail sync settings as described on the homestead site. I had the exact thing happen a number of years ago and it was due to Homestead allowing their certificates to lapse. Please advise on how to fix this.
I do understand that we did allow our certificate to lapse a few years ago, but as soon as I saw your post, I checked it and they are current. If we had an issue with our email certificates, trust me, HUNDREDS of customers would be posting about this. Obviously, there was some type of error, because you are one of 3 people experiencing this issue, but one of the other people who reported this experienced success restarting their device. Have you restarted your computer?
It is happening on all of my accounts. It is not just one email account so it leads me to believe there is a larger issue. Yes I have restarted my computer. It is happening on all of my homestead email accounts on both Outlook 365 (Web) and Outlook desktop.
We have reached out to make sure our certificate has properly renewed. Restarting the program and/or client is an attempt to refresh the renewed certificate, but if the error still disallows you to send we can recommend re-setting up the Email address in the client once more to see if that resolves the issue.
The same thing is happening on both of my Homestead-hosted email accounts on my iPad, iPhone, and iMac, each of which has been restarted several times, along with restarting the Mail apps on each device.
I just contacted Apple Support. They insisted that there is no caching of certificates on the iMac, iPad, or iPhone. They said that if I deleted the expired certificate (which expired May 14, 2022 at 7:00 pm) in Keychain Access on my iMac, and then tried to send an email, that should force Apple Mail to retrieve the current certificate from the Homestead.com server. However, Apple Mail once again retrieves the expired certificate (which is flagged as invalid) rather than retrieving the current certificate (which shows as running from April 26, 2022 to May 27, 2023). Apple Support said it must be Homestead's server that is supplying that expired certificate. I have now deleted the expired certificate four times, and each time, when I try to send an email, instead of getting the current certificate, I get the old expired certificate from somewhere. As I said, Apple Support insists there is no place where the expired certificate is cached, so the expired certificate is coming from somewhere outside of my three devices.
Below is the newly-retrieved but expired certificate that shows on my iMac's Keychain Access after I deleted the expired certificate. As I said above, I've done this four times now:
I just solved the problem on my iPad, iPhone, and iMac for both of my Homestead-hosted email accounts. Some time ago, I suddenly had problems sending and receiving email on my Homestead-hosted email accounts. When I called Homestead Support at the time, they advised me to change the Port for the outgoing mail server from 465 (which I'd used for many years) to 587. That solved the problem.
So now, in experimenting, I noticed on my iPhone that if I tried to configure a new outgoing SMTP server, it defaulted to Port 465. So I just tried changing the Port for the outgoing mail server from 587 back to 465 for both email accounts on all three devices. On the iMac, I first deleted the expired certificate in Keychain Access. Both accounts on all three devices are now sending emails without error. Curiously, I see no new homestead.com certificate in Keychain Access.
I have no idea why this fixed the problem; perhaps Homestead Support can explain why.
I am having this issue with one of my 2 emails. I restarted my laptop. Didn't fix it. One account has the renewed certificate and the other doesn't. I have a lot of trouble with people not receiving my emails... been that way for years. outlook asks me every time I start email if I want to trust the certificate. Seems odd I have to do that every single time I start outlook for the one account.
update. I cleared the SSL cache. restarted email. installed unexpired certificate. Still can't send emails without using the expired certificate. It lets me install the new one but doesn't use it?
it also seems like my online store isn't always sending emails using this email. I'm not getting every order emailed to me like i used to before this issue... now I worry my customers are not getting them either.
A number of people who have reported this were able to resolve the issue by either restarting their email application, restarting the device, or reapplying the settings:
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.
elyzabethv
10.6K Messages
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141.7K Points
2 years ago
Hello,
Our certificate is not currently expired. I would recommend restarting the email application or the device the application is on.
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stavros6441
15 Messages
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300 Points
2 years ago
Okay thank you. Refreshed it and I don’t get this warning now.
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matt3174
9 Messages
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374 Points
2 years ago
Email trust certificate expired
PLEASE FIX ASAP. I am unable to send important business emails. Please advise when Homestead will fix.
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joanne1404
3 Messages
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130 Points
2 years ago
I am having this issue with one of my 2 emails. I restarted my laptop. Didn't fix it. One account has the renewed certificate and the other doesn't. I have a lot of trouble with people not receiving my emails... been that way for years. outlook asks me every time I start email if I want to trust the certificate. Seems odd I have to do that every single time I start outlook for the one account.
help?
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joanne1404
3 Messages
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130 Points
2 years ago
update. I cleared the SSL cache. restarted email. installed unexpired certificate. Still can't send emails without using the expired certificate. It lets me install the new one but doesn't use it?
it also seems like my online store isn't always sending emails using this email. I'm not getting every order emailed to me like i used to before this issue... now I worry my customers are not getting them either.
0
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alice6364
11 Messages
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630 Points
2 years ago
I am getting a pop up box saying that my certificate is not secure. Please assist.
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joanne1404
3 Messages
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130 Points
2 years ago
now i can't send anything... i have installed the new certificate 6 times and it still has the expired one.
Can i get a phone number to call for help?
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techwtr
66 Messages
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964 Points
2 years 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.
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