I am trying to upgrade from Confluence 3.1.1 to 5.4.4 as per documentation it appears that there are intermediate steps involved for upgrade.
STEP1- Upgrade from 3.1.1 to 3.5.17 (please provide link to upgrade documentation)
STEP2- Upgrade from 3.5.17 to 5.0.3 (please provide link to upgrade documentation)
STEP3 - Upgrade from 5.0.3 to 5.4.4
Q1) I read that prior to 3.5 version requires manual upgrade, does it means that STEP1 will be manual and STEP2 & 3 will be via some assistant? or all step1 to 3 will be manual.
Q2) Is it possible to have fresh install of 5.4.4 and export/import content from 3.1.1 to 5.4.4? is there any export/import facility that can be used for exporting from upgraded 5.4.4 instance to freshly installed 5.4.4?
Q3) Please help me with upgrade documentations & known issues and their resolutions, that can be reffered on each of the STEPs?
Yes, your upgrade path looks correct to me.
Bascially, you've answered your own questions though. https://confluence.atlassian.com/display/DOC/Upgrading+Confluenceis the link I'd start with and it looks like you've read through this already, so you should have found the relevant links. Me posting specific documents here is only going to cover stuff you've already found by reading that doc.
Step1: Upgrade documentation: https://confluence.atlassian.com/display/CONF43/Confluence+3.5.17+Upgrade+Notes
Step2: Upgrade documentation: https://confluence.atlassian.com/display/DOC/Confluence+5.0.3+Upgrade+Notes
Step3: Upgrade documentation: https://confluence.atlassian.com/display/DOC/Confluence+5.4.4+Upgrade+Notes
Q1: All will be manual.
Q2: No you can't do export/import.
Q3: Issues are different case by case. You will most likely have problems with plugins, they act a bit differently, some become commercial, some was not anymore in 5.4.4. Trying upgrade in test environment first is a must I think.
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