Renaming rule doesn't catch words

Your Renaming Rules is using "Statement Name". The "Statement Name" is exactly what was sent by your financial institution to Quicken, but it may not be the same as the name displayed as the Payee in Quicken, because Quicken's server-based renaming rules try to clean up/normalize Payee names.

Click on one of those transactions and select View > Show Inspector. Look at the "Statement Payee" near the bottom. I'm guessing it does not contain "Jack Plumbing" as two separate words. If so, you can change one of two things: (1) Change the renaming rule to use "Quicken name" instead of "Statement name", or (2) change the rule to use the text you see in the Statement name field of the transaction you've examined. Either way should now match your existing transactions.