Two iPhones from clients can’t send email over a perfectly normal IMAP/SMTP email account. iOS 18.4
The account is perfectly fine on my own iPhone 13/iOS 18.4
Settings are definitely correct. IMAP receiving is fine.
On my own iPhone SMTP with port 465 and SSL on is fine as it should be.
No luck on both of these client iPhones, not on cellular, not on WiFi. Emails just don’t go out, the only message is “Can’t send” with no reason given.
The only oddity we know of is that both iPhones are US models. These guys have recently relocated from US to UK and US models can have slightly different hardware, but that should only really affect available carrier bands.
UK carrier is O2, should some Brits here read this.
There is a vast space here for problems. If you have access to the SMTP server logs, that might help in ways that iOS’s error reporting obviously won’t. Otherwise, things I’d consider:
DNS. It’s always DNS. Since your clients apparently moved recently, perhaps they are using a different DNS server from yours or have an old VPN enabled or some such.
Check that they’re really using the same SMTP server address that you are. It’s been a while since I’ve used iOS SMTP, but IIRC, Mail buries some SMTP settings deeper than the IMAP settings.
Are the phones that don’t work on the same network (NOT just the same carrier) as the phone that works?
I vaguely recall that Mail had a “configure automatically” switch that would toggle itself at inconvenient times and mess up or override settings. You might look to see if that’s still a thing.
Good luck. “[P]erfectly normal IMAP/SMTP” is, unfortunately, an oxymoron.
The ports used for SMTPS vary. I’ve seen 465, 587, and even sometimes the old 25. I’ve also seen providers where the instructions or autoconfig are wrong (maybe merely out of date). It might be worth trying the other common ports.
Can you point to the hosting provider’s instructions for SMTP set up?
The requirements for SMTP can include…
SMTP server
Server port
User name and password to authenticate to server
Use SSL?
Sending email address
Sending network
Some SMTP servers use STARTTLS rather than SSL, on an iPhone this would be denoted by the server port.
The sending email address and sending port is often significant. For example, if you’re sending through Apple’s SMTP servers you must use a .Mac, MobileMe, or iCloud From: address. And some SMTP servers only allow you to send through them if you’re on their network.
And, for authentication, some servers require you to generate a special id and password that is different than you’d normally use.
Thanks @befr
Webmail is fine.
Using this user’s credentials on my own MBP works.
At the moment, my theory is that it’s some obscure security software that the users are not aware of and therefore can’t name. Over an hour’s drive away and no remote access yet.
If he is logged in with his Apple-ID:
In your Finder select goto->connect to server and enter
vnc://hisAppleID
He then has to allow you to login.
Works great on occasions where you have to “see” the problem.
Thanks @befr for further suggestions.
I’ve already been through with 2-hr video calls to “see” the problem.
(As an aside, vnc has for us been notoriously unreliable, We use ANYDESK, but users need to be patient enough to go through an initial setup. Easy for you and me, but not for everybody.)
Do they get an error message, or something that says what the failure is when they try to send an email.
Then if you have access to the server logs you could see what it says there. Some servers require authorization for outgoing mail as well, and some times that needs to be set up in the phone separately.
At least it’s a Mac now. Start protocol logging (Window, Connection Doctor, tick the box), send some mail, see what the log says.
It does sound like you’ve isolated the obvious causes if you’re able to set this up on your own machine, so there’s probably some other software messing things up, but still, should be interesting to hear what you find.
Setting up IMAP accounts on iOS is trickier than it should be in my experience (we run a mail server with about 4500 mailboxes on it). I’ve found that using a configuration profile is a pretty solid way to get iOS devices set up reliably. Are you able to create a profile? (in our case we use Mailcow and it generates these by default, which is a nice feature). I’ve also found that pre-existing configuration profiles can be a pain if you don’t know what they are doing, and you are trying to set up an IMAP account. I’m wondering whether these devices have pre-existing profiles installed that are somehow getting in the way (for example they might be locking down some settings that stop the SMTP config from being created). I’ve seen something like this recently on a Macbook.
Hooray, success at last. Oddities found included:
Two Gmail accounts, one half done, not working.
The “can’t send” account on “my” server.
An iCloud account that was sometimes working but not always.
SMPT log showed attempts to connect on port 0, despite this not being set like this.
I cleared out all of these accounts, and se them up from scratch. All of them instantly worked OK. Same therapy for the iPhones and an iPad. Everything worked as planned.
The automatic setup sets it up as SMTP port 587 with SSL ON.
@graham.mitchell Yes I thought about profiles and can generate them on the server platform. Unfortunately they don’t work, despite intensive support and research about the reasons. The generated profiles were once verified by Apple support as being correct/valid, yet they don’t work. I have seen them in use elsewhere a while back, but was only ever on one out of several dozend occasions able to use them, I never tried again.
