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Failed Outgoing Emails

Avatar Rick Churchill
On occasions my outgoing emails “fail” with a notification headed “Cannot send the message using server iCloud” with a suggestion I use another server. with a list which are iCloud, Google and two Talktalk servers which I presume represent my 4 accounts.

When I click on Edit SMTP Server list it shows only the two Talktalk email addresses
When I click on Connection Doctor it shows a list with a:
Green dot against
iCloud SMTP
iCloud IMAP,
Google IMAP,
Commercial and Personal POP which are the names I use for my Talktalk email addresses

Red dot against
rickchurchill1@talktalk SMTP (this is “Commercial”)
Talktalk SMTP (this is “Personal” well actually [undisclosed email])

Now I am not interested in Talktalk anymore as I have changed to a full fibre Broadband supplier so at the end of September I will lose these and my preferred email address for a long time has been iCloud.

Turning the MacBook off and on again hasn’t worked and force quitting email either.

I cannot remember how I was able use email later but I believe it just corrected itself but at present I cannot wait as I am in constant communication with my overseas brother planning a holiday and I desperately need to have a reliable communication channel.

I tried sending a shorter test message without all the attachments in case the attachments were the cause and got a similar Can’t send message but this time advising
“An SSL error has occurred and a secure connection to the server cannot be made.”

Am going to bed now because whatever hair I had on my head is now on the floor!

Any help you give will be much appreciated.

Addition: I've successfully sent an email from my phone using the same WiFi/Broadband route to the iCloud server without problems so it is the MacBook that has some fault

Re: Failed Outgoing Emails

Avatar Mick Burrell
I suspect you already know Rick but you cannot send via the iCloud servers using a non-Apple email address - this isn't what's happened?

Re: Failed Outgoing Emails

Avatar Rick Churchill
Thanks Mike. No I'm sending emails from my iCloud email alias (but I have also tried from the normal iCloud address). Unfortunately the problem has persisted so am surviving using my phone.
Is there a way of re-installing the app without losing the email address, its aliases and any existing messages stored on my Mac and in the cloud?

Re: Failed Outgoing Emails

Avatar Mick Burrell
You could contact Apple for help but I suspect they'll suggest you delete the account on the Mac then set it up again.

It's an IMAP account so you should be able to delete the account and set it up again. You won't lose any mail stored "on my Mac" or on the iCloud servers. I suspect the aliases will be fine too although you may have to enter them as an address to use on the Mac.

Re: Failed Outgoing Emails

Avatar Rick Churchill
Yesterday it took me an hour of conversation with Talktalk to get them to end the contract with them. Today I'm having difficulty deleting my iCloud email account on the Mac (so I can reinstall it.) Here is what I have done.

In Mail > Settings I selected the iCloud account and clicked the minus sign at the bottom to delete the account and I get the message
The iCloud account “[undisclosed email]” is shared by other applications on this Mac.
You can remove this account in Internet Accounts.

On the Internet Accounts page to which I am directed, In "Apps using iCloud" I turned iCloud Mail to off. Under "iCloud+" I have left Hide my email and custom email domain as they are.

When I try to delete the account in Internet Accounts there is a message
Do you want to keep a copy of your iCloud data on this Mac before signing out?
I’ve clicked “Keep a Copy”

The question appears again when I click delete Account.

Please can you advise me where I am going wrong

Re: Failed Outgoing Emails

Avatar Rick Churchill
SUCCESS The email account had been deleted with no acknowledgement so I was unaware that it was missing. Reinstalled I am able to send messages although the original message still would not go but I've now deleted it.
Thanks

Re: Failed Outgoing Emails

Avatar Mick Burrell
Glad it worked

Re: Failed Outgoing Emails

Avatar Rick Churchill
The problem quickly returned and I had a few sessions with Apple to sort it out. We changed so many things and the expert went so fast through the plan he had devised during his second call that I'm not sure which thing did the trick.

Anyway he thought it was to do with synchronising mail between the cloud and the Mac. He also made a new "location" rather than used automatic. He said this reset a number of things which may have been corrupted.

He talked a lot about VPN which I don't have but one of the earlier lesser experts may have inadvertently miss-noted.

All's well that ends well

Re: Failed Outgoing Emails

Avatar Rick Churchill
Just to advise that my difficulty in sending email attachments from my Mac using an iCloud account persists. (I am able to send from gmail and from my iPad). I have had several sessions and have sent Mr Apple in the USA a couple of logs. It is now being upgraded to "engineering".

Re: Failed Outgoing Emails

Avatar Rick Churchill
***SOLVED***
I sent further MacBook files to Apple engineering but no solution was forthcoming so when I realised that Apple emails with attachments worked with other WiFi networks I discussed the problem with my ISP provider, Toob and they knew of the issue with MacBook computers and asked me to alter the following:

System Settings > Network > Details > Hardware > MTU > Alter “1500” to “1280".
(To do this Configure had to be set to “Manually”)

Toob's did not respond to my email which their system shows as not received for some reason but their telephone response was immediate and I was very pleased with their service. They advised that Apple have an update coming early next year to help small ISP companies like themselves. They in no way blamed Apple and (I think I have this correct) said it was because of the fact that they (Toob) used Dynamic IP addresses and Apple servers thought that the extra traffic was spam related.

As I understand it MRU is Maximum Transmission Unit above which the packets of data get fragmented and my new ISP could not handle such a large size. What this has to do with spam I am unsure.
 
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