Mailreport and outlook.com

[maxbet]

I had configured pfSense to send me alerts and daily reports via a company server (Postfix); this setup has been working flawlessly for more than 4 years.
Recently I needed to change the mail server to Outlook.com, so I modified the SMTP configuration in System:advanced/notifications. I only modified the server info and account data, double checked and tested the configuration : I successfully received the test email in the Outlook.com account.
For the past few weeks I could only receive alerts but no daily reports at all. Same if I force one report to be sent now.
I tried many combinations, including erase the report and create a new one, but still have only alerts.
Did any one experience the same problem?
Any idea how to fix it or debug it?

Max

[Gertjan]

@maxbet:

….
For the past few weeks I could only receive alerts but no daily reports at all. Same if I force one report to be sent now.

So, sending a 'test' mail works.

@maxbet:

….
I tried many combinations, including erase the report and create a new one, but still have only alerts.

No need to change your setup, as it works, pfSense can deliver mails through your mail server, outlook.com
Focus on the part that generates this alert mail.

@maxbet:

….
Did any one experience the same problem?
Any idea how to fix it or debug it?

Noop.
As you already know, and I know : ones you have your own postfix server, you shall not leave it. It's simply the best thing to deliver and send mails - easy to test. You control the whole chain (except the receiving part, of course, but that can never be your problem, it the receivers problem … ;))

Btw : I'm not using them, but have very good experiences with the gmail's smtp servers.
imho : Outlook (msn, hotmail, whatever ..) : maybe good enough for private stuff, not to be used outside that scope.
Max

[maxbet]

Gertjan,
thank you for your answer.
Current situation is :

• Sending test email works with Outlook.com

• Alert emails (e.g. UPS events or Gateway events) are sent

• Mail reports are not sent

Unfortunately I cannot use Postfix any more (I am leaving the company), therefore I am forced to switch to outlook.com. Furthermore : I am in China and this limits the selection of email providers I can use (Google does not work here and I already tried with pfSense, but no success).
I will try to switch back to Postfix and confirm that the issue lies in the switch between the two systems.