Verifying a updated mail certificate on iPhone/iPad

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Level 1

106 points

Verifying a updated mail certificate on iPhone/iPad

I recently signed a self signed certificate that was about to expire on my High Sierra server. Now I am unable to connect on my iDevices while I can on my Macs

When retrieving mail from my Mac I was able to accept that certificate and use it for sending and receiving mail. On the iDevices, I get a pop up saying "cannot verify server identity." I was able to view the details of the certificate yet, unlike on the Mac, I am not able to accept it. I have tried deleting the account and when I go to create it again, I get a message first that it cannot connect using SSL and then when it tries to set it up without SSL it claims "No password provided for [server_name] and that should go to mail account settings to enter a password, but I did with Settings>Accounts>Add Accounts>Other>Add account. (Again this is a personal High Sierra Mail Server). Once again, the Macs can connect just fine.

I have been able to do this in past when I have updated the self-signed certificate. I am not sure why it is not working this time. I have tried using mail.[server}.com and have tried using the IP address. The response I first get is cannot connectives SSL and when I try and connect without, I get a message that it cannot connect to mail server. The account settings were entered exactly as they appear in the Mail App on the Mac under Mail>Preferences>Accounts

How do I fix this?

Paul

iPhone 6, iOS 10

Posted on Sep 5, 2021 9:02 AM

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Answer 1

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Paul Kleeberg Author

Level 1

106 points

Sep 7, 2021 11:15 AM in response to Paul Kleeberg

The two excellent responses I got above along with the website I mentioned in my previous message help me get that certificate installed on my iPhone.

The other issue, "No password for server" was solved with a little voodoo. I don't know what truly solved it but I created a new SMTP server, I turned on SSL and then I finally got the pop-up telling me that the certificate was not trusted and if I wanted to continue. I click continue and everything worked just fine. It appears that entering the certificate as was described above didn't seem to make a difference since one of my devices had that imported certificate and the other did not.

Bottom line, everything is working and thank you all for your help.

Paul

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Answer 2

ace1018

Community Specialist

Sep 6, 2021 7:48 AM in response to Paul Kleeberg

Hello Paul Kleeberg,

It sounds like you're unable to connect iOS devices to your computer after updating a self-signed certificate, and we're happy to help. In some cases, server settings for mobile devices and computers can be different. To ensure you have the correct server settings, we recommend trying to look them up here: Mail - Official Apple Support

If you're unable to find the server settings for your email provider there, we recommend that you reach out to the email provider for the correct server settings.

Cheers!

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Answer 3

Sep 6, 2021 12:18 PM in response to Paul Kleeberg

Paul Kleeberg,

For information on how to manually trust a certificate, check out the following resources: Intro to certificate management for Apple devices & Trust manually installed certificate profiles in iOS and iPadOS

We hope that helps.

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Answer 4

Paul Kleeberg Author

Level 1

106 points

Sep 6, 2021 12:07 PM in response to ace1018

Thanks, ace

I tried the webpage you mentioned and neither of my mail web servers on High Sierra Server were able to return information. I am the email provider. I'm using two different Mac mini's with two different sized IPs to serve to two different domains. Mail is on both of them. They are both using self signed certificates. The max are able to accept the self signed certificates once I open the dialog , tell it to trust the certificate, and sign as the administrator. One mail server has a self signed certificate from several months ago and both the auto devices are able to use email form that domain. The one in question has a self signed certificate that was changed a week ago and neither of the iDevices are able to get past the barrier I mentioned above.

How can I get iDevices to trust the self signed certificate?

Paul

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Answer 5

Paul Kleeberg Author

Level 1

106 points

Sep 6, 2021 2:22 PM in response to barberlives123

Thank you barberlives123. That did help.

First I had to find out how to extract a certificate from the server. I found that information here: https://docs.vmware.com/en/Horizon-FLEX/1.12/com.vmware.horizon.flex.admin.doc/GUID-A471DB0B-3E8C-4397-976D-C13D130D8FF7.html. I was successful and extracting the certificate putting it on the iPhone and trusting it through the instructions that you sent to me. Problem is, I still get the same message when I try and create the account:

My experience was just as I had stated above, I had deleted the account and :

"...when I go to create it again, I get a message first that it cannot connect using SSL and then when it tries to set it up without SSL it claims "No password provided for [server_name] and that should go to mail account settings to enter a password, but I did with Settings>Accounts>Add Accounts>Other>Add account."

I am stumped.

Maybe I should create a new topic since the problem does not seem to be the certificate.

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Verifying a updated mail certificate on iPhone/iPad

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