Configure Confluence SMTP with TLS via JNDI for Office 365 Relay


How To Fix: Unrecognized SSL message, plaintext connection in Confluence JNDI

I’ve been doing Exchange to Office 365 migrations lately and that means on-premises applications and devices can’t use the local Exchange server to send mail anymore.

Your options are to use the credentials of an Office 365 mailbox to send mail, set up a local SMTP relayer, or use a third-party SMTP service.

If you’ve opted to use an Office 365 login to send mail via SMTP, then you must use TLS, so the applications/devices sending mail must support sending mail with TLS on port 587.

This article focuses on Atlassian Confluence but may apply to other java applications using JNDI to configure mail.

Atlassian Confluence, Secure SMTP, and JNDI

Confluence has no way to set up secure SMTP with SSL or TLS from within the administration, so unfortunately you’re forced to configure Confluence to use a JNDI Location for SMTP. This involves moving around JARs and changing configuration files, which will end up slowing down your upgrades (see my script to make Confluence upgrades easier).

Continue Reading »

Use jTDS NTLM Authentication in Confluence with SQL Server

I run Atlassian’s Confluence in several organizations. It’s a great product and runs on many platforms. Being a Windows admin I tend to stick to the existing Microsoft stack where possible, so I typically run Confluence on Windows against Microsoft SQL Server. The jTDS driver that comes with Confluence wants to use a SQL server user and can’t use NTLM/Windows authentication out of the box. With a few simple changes, we can have Confluence using NTLM auth to connect to SQL Server.

Continue Reading »

Simplify Confluence and JIRA Upgrades on Windows

The new installer for Confluence and JIRA on Windows simplifies upgrades, but it also overwrites added or modified files in your program directory. If you have added or modified a lot of files, it can be tedious to restore those modifications after the upgrade. To that end, I’ve written a simple powershell script which will back up all of the modified files and then optionally restore the files once the upgrade is complete.

Continue Reading »