Emails won't send with SSL enabled from iPad

[#1]

Hello,

My wife's iPad has suddenly stopped sending emails.  I have checked the settings - all OK - and reinstalled Mail, to no avail. I can get it to send mail with SSL disabled, but  I'm worried that the emails will no longer be encrypted.  The outgoing port is 587 (I tried 465 but no go). The iPad is a Mini 4, IoS is up to date at 15.8.8.

Any help would be most appreciated.

Many thanks,

Dave 

[#2]

Which SMTP server are you using ?

[#3]

Thanks for your speedy response Philip.  I'm pretty dim when it comes to the workings of email; are you referring to the outgoing settings?  If so, that is set at relay.plus.net 

[#4]

SMTP ( out going ) server : relay.plus.net  does support encryption.

SSL/TLS via Port 465

STARTTLS via Port 587

[#5]

Thanks once again Philip.  I have deleted the account, restarted the iPad and reinstalled. The outgoing server details are as below:

Error messages I'm getting:

The iPad mini 4 appears to be no longer supported; could this be the problem?  Email on own iPad 7 (IoS 16.6.1) works perfectly with the same settings (except my Plusnet email address).

Note that I have added  her password and username in the outgoing settings.  Is this OK?

Many thanks once again for your help with this.

Dave

Moderator's note(s):

First picture edited to make personal information less visible.

[#6]

@Weystoner1 

I can make out the email address in your first image, so it won't be released. Too late to change.

I would suggest using the full email address and not accountname+mailbox name to see if helps.

Edit: I have asked a moderator if they can obscure the image better.

[#7]

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@Weystoner1 wrote:

Thanks once again Philip.  I have deleted the account, restarted the iPad and reinstalled. The outgoing server details are as below:

Error messages I'm getting:

The iPad mini 4 appears to be no longer supported; could this be the problem?  Email on own iPad 7 (IoS 16.6.1) works perfectly with the same settings (except my Plusnet email address).

Note that I have added  her password and username in the outgoing settings.  Is this OK?

Many thanks once again for your help with this.

Dave

---

Very highly likely, @Weystoner1  - TBH, I am amazed such an old piece of Apple kit functions anywhere near useful.

[#8]

Many thanks Dan, I didn't notice that the name wasn't obscured properly.  I'll try your suggestion.

[#9]

Did you find a solution to this ?  
If not, are there alternate email programs that can be installed and tried ?

We have an old PC here that had MS Outlook 2010, the SSL connection failures came out of the blue when 123reg tightened the SSL/TLS security of the servers

The fix was a new install of Thunderbird and this is working perfectly with 123reg and Plusnet / Greenby all are configured with SSL/TLS enabled.

[#10]

No, I haven't fixed it yet.  It looks like Thunderbird for iOS isn't quite ready, unfortunately, but thanks fro the suggestion.  I think I'll have to go old school and give Plusnet a call.

Dave

[#11]

Try any other well known email app e.g. MS Outlook

I have Blue Mail on Android it is working with Plusnet / Greenby servers with SSL/TLS enabled and with Certificate check enabled.

[#12]

@Weystoner1   I don't have your device so this is from a bit of read up.

In the screen shot Certificate the bottom line is :  More Details >   
does this have an option to Trust the GeoTrust G5 Certificate being presented by relay.plus.net ?

[#13]

Thanks for the suggestion Philip, I'll have a look.  As to MS Outlook etc, I'm loath to go that route as my experience of Outlook hasn't been great on my Windows server, so who knows what it will do with iOS!

Dave

[#14]

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@PhilipHeyes wrote:

Did you find a solution to this ?  
If not, are there alternate email programs that can be installed and tried ?

We have an old PC here that had MS Outlook 2010, the SSL connection failures came out of the blue when 123reg tightened the SSL/TLS security of the servers

The fix was a new install of Thunderbird and this is working perfectly with 123reg and Plusnet / Greenby all are configured with SSL/TLS enabled.

---

I recently had the same problem with Outlook 2003 suddenly not working (not receiving). The inbuilt test worked no problems and it could send. Like yourself I just started using Thunderbird which displays a lot better than that Outlook ever did.

[#15]

TLDR;

If you have been migrated to Greenby you probably want to set your SMTP to mail.enmail.co, port 465, SSL/TLS.

Anyone would think DNS and X509 were difficult.

I have no idea whether relay.plus.net is still working as I am no longer a PN customer.

relay.plus.net is a PN IP and the server that answers sends a valid certificate.

X509v3 Subject Alternative Name: 
   DNS:relay.plus.net, DNS:relay.force9.net, DNS:relay.free-online.net, DNS:relay.metronet.co.uk

However, if you are not a PN customer the server rejects the login.

Greenby say to use various server host names but the certificate returned by the Greenby servers do not match all of them.

mail.enmail.co on 465 (SSL/TLS) and 587 (STARTTLS) returns a matching certificate.

Subject: CN=mail.enmail.co

X509v3 Subject Alternative Name: 
   DNS:mail.enmail.co

If you have been migrated your <mailbox>@<username>.plus.com login should be accepted.

relay.force9.net is a Greenby IP and also returns a matching certificate

X509v3 Subject Alternative Name: 
   DNS:relay.plus.net, DNS:relay.force9.net, DNS:relay.free-online.net, DNS:relay.metronet.co.uk

If you have been migrated your <mailbox>@<username>.plus.com login should be accepted.

mail.plusnet.enmail.co and every other name ending .enmail.co that was not mail.enmail.co gets an invalid certificate.

X509v3 Subject Alternative Name: 
   DNS:relay.plus.net, DNS:relay.force9.net, DNS:relay.free-online.net, DNS:relay.metronet.co.uk

Why on earth they didn't add *.enmail.co to the subject alternate name list, only Greenby knows.

Oh...Hold on. It's amateur hour. They just copied the certificate files from the PN server.

relay.plus.net Connecting to 212.159.9.107
Serial Number: 03:4d:07:ec:4a:2c:58:e2:a3:66:8d:1c:31:7e:01:23

mail.plusnet.enmail.co Connecting to 91.204.208.26
Serial Number: 03:4d:07:ec:4a:2c:58:e2:a3:66:8d:1c:31:7e:01:23