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@MarqueeCrew - Yes. I have three other flows that are scheduled in the gallery and run the exact same query. The only difference is: (1) They are referencing different tables (2) They are normal input tools.
After a call with @KevinP I was able to resolve the second issue by creating an In-DB Connection with a SQL Server Ole DB driver, replacing the SQL Server ODBC driver. In order to get this driver to work I had to make these few configurations:
Integrated Security: Open this prompt and then close it (this is effectively an "acknowledgment" of this setting in Alteryx)
Persist Security: Open this prompt and set it to "True"
Kevin also offered a solution that replaced the need for the In-DB tools altogether. He suggested using the regular input data tool and writing the following optimized query which returns the last RecordID:
Select Top 1 RecordID From Database Order By RecordID Desc
This solution, in particular, was a great reminder to leverage SQL and experiment with queries if the tools begin to pile up. Thanks for your assistance, Kevin!
@dallen Happy to be of assistance and I am glad to hear the solutions provided are working well for you. Also thank you for updating the post with the solutions as it may help other users in the future.