Outlook 2010 calendar invite being recieved as plain text

GRoston · 06 Apr 2015

When Outlook calendar invitations are sent to certain recipients, they receive a plain text email as opposed to an actual iCal file. I have been doing my research on this, but have yet to find an answer. In order to narrow down the problem, I did a tightly controlled experiment:

I have Outlook configured to access email from several different POP3 servers, with all mail being directed to the same PST file. The first POP3 server is on my personal domain - I have a Linux-based VPS where the site is manage. The second POP3 server is a GoDaddy server.

Sent via my personal domain:
I created a first event in my Calendar and invited myself (personal domain). The message in the Sent folder is a proper iCal invitation and the invitation that I received is a proper iCal invitation. I then created a second event in my Calendar and invited myself (GoDaddy domain). The message in the Sent folder is a proper iCal invitation and the invitation that I received is plain text.

Sent via the GoDaddy domain:
I created a first event in my Calendar and invited myself (personal domain). The message in the Sent folder is a proper iCal invitation and the invitation that I received is a proper iCal invitation. I then created a second event in my Calendar and invited myself (GoDaddy domain). The message in the Sent folder is a proper iCal invitation and the invitation that I received is a proper iCal invitation.

In summary, the only instance that failed was when I sent the invite via my personal domain to another domain. (While my testing is far from exhaustive, this should at least provide a strong clue as to what is happening.) And yes, the Options->Calendar->When sending meeting requests outside of your organization, use the iCalendar format box is checked.

Can anyone suggest what might be going wrong? Based on these experiments, is it possible that something on my server is configured improperly? If so, what? (I did a further test and sent myself an invite via an Exchange server, and it showed up properly - thus I suspect even more strongly that the problem is with my server.)

GRoston · 13 Apr 2015

I left out one, potentially important bit of info: Outbound emails from my server are routed through MandraillApp. Some further testing seems to suggest that MandraillApp is the culprit. Has anyone else seen this behavior? If so, any suggestions for resolving the problem?

Windows Sniper · 13 Apr 2015

Have you tried turning off the auto_text option in the server?

Mandrill - what does auto_text do? - Stack Overflow

Also, feel this should be moved out of the MS office sub.

GRoston · 13 Apr 2015

Windows Sniper,

Thank you.

You are probably correct about moving it, but I could not come up with a better fit. My reason for posting here is that this forum's regulars are amongst the most helpful and I am really looking for an answer.

With regard to your reply: You suggestion may be spot on, but i was not sufficiently clear in my original post. I have simply configured postfix (my STMP server program) to relay outbound mail via smtp.mandrillapp.com. Thus, I do not have programmatic access as described in the referenced post.

Windows Sniper · 14 Apr 2015

GRoston said:

Windows Sniper,

Thank you.

You are probably correct about moving it, but I could not come up with a better fit. My reason for posting here is that this forum's regulars are amongst the most helpful and I am really looking for an answer.

With regard to your reply: You suggestion may be spot on, but i was not sufficiently clear in my original post. I have simply configured postfix (my STMP server program) to relay outbound mail via smtp.mandrillapp.com. Thus, I do not have programmatic access as described in the referenced post.

No worries, i've sent the mods a message anyway to get it put in a more appropriate thread.

As to your issue, can i ask why you relay through the site?

If you can, and have access to do so, can you send an email without using the mandrillapp relay. I.E send it directly from your domain. This will be useful to test if it is specifically an issue with the application.

Also, on their knowledge doc, it states that "Inbound emails are processed based on the routes you've set up, and messages matching the routes are sent to your specified URL(s) as a webhook."

Meaning that you should have some level of control in regards to how you emails are received.