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iPod touch Secure connection failed. Certificate for my@email.address.com may not be valid

I

iPodTouchOwner

macrumors member
Original poster
Jan 17, 2015
39
0
I've been using my email accounts for years from my iPod Touch. It is from my WiFi network at home. A few days ago, I got "Secure connection failed. The certificate for myEmail@server.address.com may not be valid. Cancel/continue". A google search indicates that this is a rampant problem encountered by iOS users. The solution seems to be to simply select Continue. I'm not a security expert, but from what I've read up on, it's not a good idea to proceed when certificates for the host do not match. Apparently, it opens up the communication to well known attacks.

Can anyone shed some light on what would cause this certificate error when things worked fine previously? And why exactly is the prevailing wisdom to proceed despite the error? The explanations I've seen are rare and very vague (something about domains and host names, but nothing convincing). I don't get such errors when accessing my email from other devices on the same home WiFi, e.g. Firefox from a Windows 7 machine.
 
I erased all accounts, erased all history/cookies//cache (which was the web-recommended way to remove certificates), and recreated one account. Same problem. Looks like I better get a move on getting my Moto G working.
 
Yes, it was an hour off yesterday. I manually fixed that, but still experienced the same problem. I even tried it from public WiFi (MacDonald's, where I had no problems in the past) but the problem persists.

I think that a key part of my problem the ambiguity about what is meant by "continue". If it means continue communicating with the server even though the certificate is wrong, that's bad. If it means continue with something else...I guess that would depend on what that something is.
 
iPodTouchOwner said:
A few days ago, I got "Secure connection failed. The certificate for myEmail@server.address.com may not be valid. Cancel/continue".
Click to expand...

You can look at the details in the certificate message to see why it's reported as invalid. For instance, I get an invalid hostname message with my personal domain email, because the mail server is actually the hosting provider's email, but I expect this, and the certificate is valid for that host, so I click continue.
 
How doe I access the details of the certificate message? The only text in the message that I can see is what is posted in the subject line of this thread. This is a 1st generation iPod Touch. The "About" info says version 3.1.3 (7E18).
 
iPodTouchOwner said:
How doe I access the details of the certificate message? The only text in the message that I can see is what is posted in the subject line of this thread. This is a 1st generation iPod Touch. The "About" info says version 3.1.3 (7E18).
Click to expand...
Oh, it's been many years since I've used iOS 3, I have no idea. Newer versions of iOS allow you to see the certificate details. It may be because the OS is so old that the certificate isn't recognized, or that one of the root certificates has expired.
 
Well something has to have happened within the last week to cause the certificate not to be recognized. It was working fine until recently. If it's a "root" certificate expiring...I don't know what that means, but it sounds like a nail in the coffin.

Anyway, I'm trying to get my replacement smartphone up and running. Looks like I ran out of rope.

Thanks, and I appreciate your input about the possible explanation.
 
iPodTouchOwner said:
Well something has to have happened within the last week to cause the certificate not to be recognized. It was working fine until recently. If it's a "root" certificate expiring...I don't know what that means, but it sounds like a nail in the coffin.

Anyway, I'm trying to get my replacement smartphone up and running. Looks like I ran out of rope.

Thanks, and I appreciate your input about the possible explanation.
Click to expand...

Given that iOS 3 hasn't been updated in nearly 5 years, it'd be prudent to move to a newer device, just for security purposes.
Root certificates are, more or less, what tell your device where to verify a certificate. These certificates have an expiration date, and there are many more of them than there were in 2010 back when iOS 3 got its last update. It could be that your mail provider's certificate expired and the new one was moved to a different certificate authority that isn't included in iOS 3. Wikipedia has more detail: http://en.wikipedia.org/wiki/Root_certificate
 
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