HT4061 Emails not being delivered via mac mail - recipients claim not receiving

A colleague and I have discovered over last 2 weeks issues with mac mail.
Emails are not being received - but it appears to be RANDOM.
We both use mac mail and have .me accounts.
He sent a group email that I never received until 3 days later when another colleague NOT on mac mail replied to all and I saw that I never received original note.
This colleague sent email to his attorney weeks ago -- and it was just delivered to his attorney's inbox YESTERDAY.
The colleague has also send me a several SENSITIVE correspondences that he confirmed via phone last night that I have still NOT received.
What is going on? is is a mac mail issue or an iCloud issue?
Need some help to get this reported and resolved.
thank you!

bingo123 wrote:
sorry gg30340 , Yes webmail works fine and I can receive from Outlook fine, just sent emails seems to disappear into a black hole from Outlook
Hi. Welcome to the forums.
For info, CP (Critical Path) has been in use for a few months now for the conversion from using Yahoo! mail servers.
What version of Outlook are you using ?
In the smtp setting, try removing @btinternet.com or @btopenworld.com from the username - despite what the online help might say.
You might like to try port 25, with No security or SSL/TLS setting.
Is it all emails that are failing to send ?
If emails have been fine for years, do you know what the previous settings were ?
As for disabling firewalls - this doesn't always help - as they can still block emails! What security package are you using, and have you checked the settings within that package ?
Sorry for the extra questions.
http://www.andyweb.co.uk/shortcuts
http://www.andyweb.co.uk/pictures

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HT4061 Emails not being delivered via mac mail - recipients claim not receiving

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