mail.hispeed.ch and Outlook for Mac

AkeWallin · 2021-05-06T13:37:26+00:00

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AkeWallin

Since a few days we have problems with our Outlook for Mac (V16.48 which is the latest) and sending certain types of mails using the UPC mail server hispeed.ch (all settings according to the latest UPC recommendations). E.g. sending a PDF (approx 200kB in size) or images. Plain text works fine as far as we can judge.
The problem is that the Outbox does not synchronize with the mail server. It just gets stuck.
Before this an Verify Certificate message pops up with the message: “A secure connection cannot be established with the server smtp.hispeed.ch. Do you want to continue?”. If I click ‘Continue’ it just gets stuck on the Outbox.
However, if I click the ‘Show Certificated’ button the mail.hispeed.ch issued by GlobalSign GCC R3 DV TLS CA 2020 shows up. An option is to ’Always trust “mail.hispeed.ch” when connecting to “smtp.hispeed.ch” and then click ’Continue.
This causes a ‘Sync Error’: “vie01a-pemc-psmtp-pe11.mail.upcmail.net vie01a-pemc-psmtp-pe11.mail.upcmail.net ESMTP server ready” with details “Email could not be sent.” (this does not seem like a very useful piece of information!) and error code ’17099.
Any ideas or hints?
Thanks a lot for any useful help!
Åke

adrianlondon

What are your outgoing / smtp server settings?

I’ve just done some tests and it’s all working fine for me. I don’t use Outlook but use Apple Mail, however I assume the config would be the same.

AkeWallin

Hi
Thanks for looking into this. And yes, I can confirm that with the Mac Mail it works fine for me too!
However, with Outlook it does not work.
This problem started occurring, we think (but who can be sure these days), when updating Mac OS to Big Sur 11.3. Possibly Microsoft needs to update Outlook accordingly.
I posted this here to the UPC Community in the hope that someone had resolved it.
Thanks a lot!
Regards,
Åke

Daniele_Sunrise

AkeWallin Welcome to the UPC Community!

Can you please post some screenshots from Outlook with the SMTP server settings? We will be happy to check if they are correct.

The correct settings can be seen here in the DATA FOR MANUAL SET-UP section.

Greetings
Daniele

AkeWallin

Daniele_Sunrise

Hi Daniele

Thanks for replying so quickly!
As far as I can see the settings are as recommended by UPC. I tried both port 587 and 465.

I would like to point out two things:

Outlook works fine for plain text
Mac Mail works fine for images and PDF
I.e. we have two workarounds at hand

Thanks and regards,
Åke

Daniele_Sunrise

AkeWallin Everything seems to be correct, because you can send mails without attachment.

Let’s have a look at some things:
A) Call the command “Tools, Options, Mail Format” in Outlook. Have you set HTML there? If not, please choose HTML.

B) Do you have an antivirus software installed in which is set that on Outlook it should scan the attachments? Can you deactivate your antivirus once for a test dispatch?

C) Do you have the error only with a certain e-mail address as or does it not matter which e-mail address you write to?

Greetings
Daniele

AkeWallin

Yes, you are on to something!
First, the things that it is not:
A) HTML - this was already the case
C) It is independent on address.
So leaves us with:
B) We use Norton and if switching of ‘Vulnerability Protection’ I do not get the error message.
I will contact Norton on this issue. If I get a resolution on this, I will post it here for future reference.
Thanks a lot for you assistance!

adrianlondon

It seems something is blocking the use of the certificate that’s required for SSL to work. When you click “continue” it’s probably not trying to use the cert anyway, but instead drop out of SSL and use a non-encrypted method for sending the emails. Many providers and email clients block this (sometimes it’s a setting to block a fall back if SSL fails).

Edit: Ah, I’ve just seen you use some anti-virus software that’s blocking the cert. That’ll do it!