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Some learnings below from various Liferay upgrades that I have been part of:

• Upgrades need us to plan various dry runs in advance on non-production environment
• Divide your upgrade between core / database and non-core upgrade
• Core includes Liferay engine, configurations and database
• Non-core includes themes, custom code, integrations and such
• Understand how to use database upgrade tool for core upgrade
• Logging of upgrade should be at much more verbose level than normal
• You can upgrade with document library or without it using portal-ext.properties configurations
• Upgrades between DXP from 7.x to 7.x are easier whereas upgrades from 6.x to 7.x need more planning
• For database upgrade tool, you have an option of 3 property files or you can use command prompt to enter required details
• Make sure you are at the latest version of whichever 7.x you are upgrading to
• Bad and corrupt data are perpetual problems which need to be analyzed properly before upgrade
• Use groovy to fix bad data not SQL
• Consider analysis and compliance from Liferay compatibility matrix, Liferay whitepapers on cloud, security, upgrade & scaling before planning your upgrade
• Create a template document for upgrade with all major areas pre-covered in analysis via the whitepapers on Liferay.com
• Understand the breaking changes with every major version release
• Learn to use the upgrade planner for code upgrade
• Docker containers are available and should be considered
• Consider headless, clustering, cloud, advanced file store, CMIS repository options right at the analysis phase of Liferay upgrade
• For your data storage requirements in future as per scaling – understand and analyze the load to confirm to the right choices of infrastructure like Cloud, SAN / NAS and so on
• Learn to use the basic Linux commands (if you are using Linux) like top, free, tail, ps, grep, liferay bin commands, sudo, vim, thread dumps and such to monitor / manage the upgrade well
• Look at top thread dump analyzers like: Smart Java thread dump analyzer – thread dump analysis in seconds (fastthread.io)
• Consider learning basics of operating system / network you are using, JVM & database tuning / optimization for threads, core allocations, monitoring and using Eclipse IDE to analyze threads, heap, etc.
• Keep reference guide for system.properties and portal-ext.properties handy during upgrade of core part
• Keep headless, GraphQL, Liferay / Java API details handy during code upgrade
• Explore 7.4 DXP features if you are upgrading to this version: Liferay DXP 7.4 New Features
• Refer help center articles and open documentation both, they have lot of good, useful content
• Reference: Upgrade Basics — Liferay Learn