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Level 1: Cadet

Problems sending email from the built in Mail apps on Mac and iDevices

What do you do when your built in Mail apps stop sending email via Telstra Mail (the useless new email sevrer deployed by Telstra ove rhe last 12 months)?  Don't pay the Premium support fee until you try this that is for sure.

 

History

 

This household has 2 MacBook Air laptops, 1 iPhone 5s, 1 iPhone 6, 1 iPad Mini and 1 iPad Pro.  We have 4 Bigpond email addresses, 3 of which have been transferred to the new Telstra Mail server and 1 that is still on the Bigpond Server from 1999 because Telstra haven't been able to transfer it after 6 attempts over 12 months.  (Another story not being told here)

 

All 6 Apple devices had been set up to send and recieve emails from the various accoutns and had been working since February 2017 without an issue.  Email was being received and sent flawlessly the whole time and as recently as Friday May 26th via both the Tesltra Mail hosted accounts and by the Bigpond Mail hosted account.

 

Then Telstra changed something on the Telstra Mail server between Friday evening and Sunday morning that stopped the Apple devices from sending email via the Telstra Mail hosted accounts.  What that change was they are not saying even after I spent over an hout on chat this morning to attempt to solve the problem.

 

Error

 

On Sunday 29th May when trying to send an email via the Telstra Mail server the iDevices started prompting for the password associated with the sending account.  On entering the password it would reply with "Unable to verify.  User account or password is incorrect".  So we tried to send fromt he Mac devices using the same Telstra Mail hosted accoutns and got the same error.

 

This of course was not true as the same user account and password were woring fine to receive mail from the imap.telstra.com server, it was only the smtp.telstra.com server that was having a problem with the user account and password.

  

Telstra's Solution for iPad and iPhone

 

After almost half an hour of chat with the email support centre and being told that the issue wasn't Telstra's but my Apple devices and they couldn't help because they don't know Apple devices, I was put through to a Mobile consultant and spent another hour working through how to get the iDevices sending email again. She eventually figured out a solution that involved going into the settings and removing the username and password from teh SMTP configuration.

 

Then she put me back to the email support centre to work on the Mac which was a waste of another 30 minutes of my life before I was offerred Premium Support at $15 per month to have someone log on remotely and "fix" my Mac.  After all it wasn't a Telstra issue so I needed to pay to have it fixed.

 

My Soultion for Mac, iPad and iPhone

 

  • Log on to your email account via WebMail.
  • Change your password
  • Wait 10 minutes
  • Change your password on your SMTP account settings.

I hope my 4 hours of frustration helps someone else.  No need to sign up to my Premium Support offering or pay me $15 a month as I don't have such an offering or charge.  Sorry if this solution doesn't work for you.  It is just one solution for my error case.

 

Bottom Line

 

I'm no expert on the Telstra Mail server infrastructure, however I have set up enough email servers in my time to know that these things don't just stop working without someone making a change.  Despite Telstra's consultants insisting that it was an Apple update that cuased the problem I know for a fact that NO UPDATES occurred on any of my Apple devices in the past 48 hours.  I trust Apple's ability to make changes properly only slightly more than I trust Telstra's abilities and thsat is not at all.  Therefore it is plainly claer that Telstra made a change the the smtp.telstra.com server either on Saturday 27th or early Sunday 28th May that invalidated the passwords on my 3 accounts and probably many others that they are not willing to admit to for fear off consumer backlash.

 

This caused Mail on Apple devices to stop authenticating with the IMAP server.  It also stopped Outlook 365 for Mac authenticating with the IMAP server (I have a copy installed on my Mac and iPad Mini but don't use it because I don't need to.  I tried configuring Telstra Mail accounts using both installations and they too came up with verfication errors until I changed my passwords)

 

By removing the username and password on the iDevices the need to authenticate with the IMAP server was removed therefore sending email started to work again.

 

On the Mac the account set up is more secure than iDevices so it is not possible to remove the username and password from the SMTP setup. Therefore the same result could not be achieved by removing the username and password on the Mac account settings.  So the only way to get it working on Macs is to force the password on the SMTP server to synchronise with the IMAP server and the only way to do this without finding the one person in Telstra that knows how to do it is to change your password.

 

 

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