Bigpond email fails to send from Iphone

[Zap69]

Trying to send a bigpond email from my Iphone, but it fails with 'Cannot Send Mail'

The connection to the outgoing server 'smtp.telstra.com' failed.

Why is this happening?

[Jupiter]

Has it been working previously?

Have you updated iOS since the last time you successfully sent an email?

[Zap69]

Can’t remember the last time it worked. 
it has been failing to send for months 

yes, I have done iOS updates too. 

[Jupiter]

The first thing I would try is to re-enter the account settings.

Account type:

Account type: IMAP

Incoming server details:

Incoming server address: imap.telstra.com
Incoming server port: 993
Encrypted connection: SSL

Outgoing server details:

Outgoing server address: smtp.telstra.com
Outgoing server port: 465 (recommended) or 587
SMTP authentication: On
Encrypted connection: SSL/TLS on port 465 (recommended) or STARTTLS on port 587

Username & Password:

User name: Your Telstra email address - ending in ‘@bigpond.com’, ‘@bigpond.net.au’ or ‘@telstra.com.’

Password: Your Telstra email account password - REMEMBER it’s case sensitive.

Other settings to check:

Make sure ‘Outgoing server requires authentication’ is ticked.

[Zap69]

Yes, I have checked and tried all the above. 
But it still does not work.  

[Jupiter]

Can you log in to you email via https://email.telstra.com ?

[Zap69]

Yes, it works fine on webmail. 
just doesn’t work on my iphone

[Jupiter]

I would delete the account from my phone and then create it from scratch.

Another thought, is your phone on the Telstra network? Are you using a VPN on it?

[oliverrat]

I am having a similar issue. I have an iphone 8+, I use the apple mail app and have my main bigpond.net.au and my sub bigpond.com set up on it. About a week ago the bigpond.com account started saying cannot get mail. In the end I deleted the account but now I cant add it back in, I get an error that SSL is not available, So I have tried to check my mail via safari app, chrome app and google app, edge app, firefox app for both bigpond.com and bigpond.net.au today and on all of them it says the page is not private, its not a private connection, connection untrusted and this is the https://signon.telstra.com.au/login

I can access the bigpond.com email via my laptop mail browser and various web browers but just not on my phone. Any ideas if there is a setting stopping this from happening. Do you think its an Apple issue? I have latest 14.3 I am not sure when I updated but I think it was in the last couple of weeks. I have also put a question on their wall and will see if I get a response.

[LG13]

I have the same issue. XS started a week ago, IMAP server not responding. Deleted account and added again, no luck. Doing IOS update now to 14.3.

Account has worked for years, no issues. Only recently paired a watch.

Works fine on IPAD / PC etc.

Bit strange !

[LG13]

Nope no change. Apple Mail just doesn't work for bigpond.  Installed "Spark" and it works fine, however it did come up with an expired certificate? But i clicked proceed and Bigpond mail works fine in Spark.

[oliverrat]

Thanks for that, installed Spark, quick and easy. I got the expired certificate thing as well, very strange. But at least I can get my emails on my phone now. Thanks for the tip.