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I'm having an issue with sending reports via email on SSRS 2016

So basically I have a VM on the Azure platform configured as an SQL server.

SQL01 (Windows 2012 Server)

+ SQL SERVER 2008 R2
+ SQL SERVER 2016 (+ SSRS)

The 2008 instance holds the data which creates the reports and the 2016 instance has SSRS installed.

I have to use 2008 as we use Merge Replication for windows mobile devices which is not supported by later SQL servers.

I have configured SSRS and the reports can be accessed via the web interface, however when I create a subscription for a report, the email never gets through.

Ideally, I want to use Office365 to handle the emails and from what I can see SSRS 2016 supports this OOB, so I configured it according to info I found including editing the config file to set the port to 587, but to no avail.

I've looked through various windows logs but cant find any errors to help resolve this issue.

I've even setup a local SMTP server to try an relay the messages to Office365 but when checking those logs I don't see any activity.

Does anyone have any idea what the problem might be or which logs are best for this, as I've been struggling for days.

Thanks.

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So couldn't work out why this wasn't working and after 2 days I got bored or searching and trying.

I did a fresh install including the Databases and it worked first time, so I assume something must have screwed up the original installation.

Not the outcome I hoped for, but at least it worked.

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