On 14.07.2018 22:53, David Babooram wrote:
Alright.

I guess the thought the process was to upgrade to 6, then 7, 8

If your application doesn't do anything too tomcat specific, but is rather a standard web application, you might be able to just deploy it on Tomcat 8.5 and check if it all works, fix problems when they appear.

Rather than migrating 3 times, check what you've configured on Tomcat 5.5, validate how to do the same on tomcat 8.5 or 9.0, and just do it. I haven't ever worried about tomcat versions - because I've never dug deeply into Tomcat, and you might be lucky to be able to work the same way.

It might be harder to migrate to a current Java version than to use a current Tomcat version.

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