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Do the drives that contain the database have to be the exact same size on the primary server as secondary? I currently have a primary database for OLTP and a standby database used for reporting. I'm going to create 2 new standby databases then cut over to them as an Always On Availability Group. The 2 AG databases must be exact matches but can't the new standby disks be different size than the current primary - as long as the drive letters match and the files fit? Thank You!

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You're confusing some technologies here, unless I'm missing something or misinterpreted. Log shipping is FAR different than Availability Groups.

Your drives on the secondary server do not have to be the exact same size, they simply need to have enough room for the DBs. That being said, it's usually a good idea to size things the same across environments that are being replicated. What if your primary DB grows and you have enough room on the primary but not enough on the secondary? That will take your replication down and cause things to break.

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