For my sins, I am the tech support for my mum and dad’s apple kit. Usually all is tickety-boo, and any issues I can easily deal with on the phone or with TeamViewer. (I am not a professional at this, purely amateur!)

With Dad’s btconnect account, and only this account (iCloud is fine), we have a bizarre issue that it refuses to send emails unless his laptop is connected to the home WiFi network. Receive is fine, but emails will not send from his MacBook Pro, or iPhone from any other network.

This is true whether he tries at his workplace, or for example when visiting us and connecting to our home WiFi. Never used to be a problem, no other settings have changed that I can see.

It is perplexing me. Can anyone understand why this is an issue and suggest a fix?

Sounds like you may need to add “apple” to the thread title

I’m a non-expert windows lad, so can’t help

Is something maybe set to only send on “trusted” networks ?

If outgoing is sending via a smtp server with no authentification then this is normal behaviour (or anyone would be able to send spam through your isp’s server. To allow sending on another network you’d usually need to use a login and password with the outgoing server.

J

What are the SMTP details he’s using?

Thanks folks – he is using outgoing mail server SMTP mail.btconnect.com

using SSL on port 995, and requires password authentication

On the iPad, it stores the inbound and outbound server passwords separately.  You need to make sure you’ve entered the password in both places (I can’t remember where it is exactly, in Account settings somewhere).  No clue about a Mac but I wouldn’t be surprised if it was similar.

With BT Internet, your username is big_scot_nannys_dad@btinternet.com, not just big_scot_nannys_dad.  You need the domain in there.

Port 993 is your inbound (POP3) port, secure SMTP should be 465.

Ah, Google.

– Mail, Contacts, Calendars
– select the Email Account
– Scroll down to OUTGOING MAIL SERVER SMTP and select mail.btinternet.com
– Primary Server and select mail.btinternet.com again
– Delete the existing Password and enter it again, select Done.

Not sure that’s the issue Cougar as it works on this home wiife, seems to be using BR SMTP on a none BT connection.

I suggest changing his SMTP details to the same as his icloud account.

It does sound like a problem with the outgoing credentials.

I’m with Plusnet and I only need to specify SMTP authentication if I’m sending emails from a non-Plusnet internet connection.  So when your Dad is connected to his home Wifi (i.e. BT) it will work without the need to authenticate.

On other non-BT internet connections (yours or work) he will need to specify valid credentials.  And as Cougar said, make sure the @btinternet.com is included.

Not sure that’s the issue Cougar as it works on this home wiife, seems to be using BR SMTP on a none BT connection.

Probably because it’s BT email address on a BT connection, they already know who he is.

I suggest changing his SMTP details to the same as his icloud account.

Yeah, this is the other way of doing it.

To send email successfully you either need to use the service provider’s (not email provider’s) native SMTP server, or you need to successfully authenticate to the SMTP server before sending.  Eg, back in the day, say you were using Yahoo email over a Pipex dial-up, you’d typically use Yahoo’s POP3 server (because that’s where your mail was stored) but Pipex’s SMTP server (because they know you’re a valid customer).  So using your iAccount should work so long as a) you’re able to successfully authenticate with it and b) Apple aren’t doing anything fruity with mail relay.

To be honest, the real solution is to bin off the BT email address and use Gmail / Hotmail / Proton Mail / any one of a million other free email providers.  Otherwise it ties you in to your ISP, so if he ever wants to change service providers he’ll have to change email addresses (or continue paying BT).  And the longer he uses it, the worse it’s going to get when that happens.

Plus, y’know, webmail. I can’t remember the last time I used a full-fat email client for non-work email on a desktop device.

To be honest, the real solution is to bin off the BT email address and use Gmail / Hotmail / Proton Mail / any one of a million other free email providers.  Otherwise it ties you in to your ISP, so if he ever wants to change service providers he’ll have to change email addresses (or continue paying BT).  And the longer he uses it, the worse it’s going to get when that happens.

Plus, y’know, webmail. I can’t remember the last time I used a full-fat email client for non-work email on a desktop device.

Yep, this is the best way.  And if you want to use a full-fat email client, use something like Mailbird or eM Client.  You can easily connect to gmail, hotmail, etc with these.

Hi folks, really appreciate the back and forward.

Yes, he already has an iCloud account which is piss easy for me to manage, but the btconnect one is for his business and pretty well known, so we’re kinda stuck with that. TBF, he is 80 this year and winding down (sort of… but that’s a whole other story!) so won’t need to worry about this email address too far in the future.

I believe we have the correct credentials, have made sure SMTP port is 465, use SSL is ticked, password authentication required.

Still receiving fine, its just refusing to bloody send. **** thing. 😆

iCloud sending and receiving just fine on MacBook and iPhone, its just the btconnect one that is being similarly stubborn on both devices. Arsebiscuits.

465 is the correct port for BT, but try 587…

Are you able to capture any errors when it tries to send?

Does he have any 3rd party firewall apps installed?

Just to confirm – have you deleted the password and re-entered it?

Oh, something else – is there an S/MIME setting?  Enable it.

And, https://bt.custhelp.com/app/answers/detail/a_id/44917/~/what-are-the-settings-for-outgoing-and-incoming-bt-email-servers%3F

Yes, he already has an iCloud account which is piss easy for me to manage, but the btconnect one is for his business and pretty well known

You can still use that the smtp is how it sends out an email, the reply and send email can still show as his BT one.

Just before I chucked the thing out the window, I had a bit of a chat with dad about his BT connect account. Importantly, he mentioned that it was set up years ago as part of a BT business deal.

After a quick google, this means that the outgoing email server was smtp.office365.com, port 587 etc etc

Balls! If I’d figured that out earlier would have been easier, and I would also have noticed that the incoming server was office365 too.

Thanks all for input, helped me feel well equipped to challenge why is was not working.

Doh! 🤪