Appears to be multiple issues on my side... I'm connecting to multiple MSSQL DBs with either a local DB account or an AD account that's been provisioned access to the database. Downgrading from sqljdbc41.jar to sqljdbc4.jar fixed my issue connecting to a MSSQL DB with a local DB account.
However, I still get an error trying to connect to a MSSQL DB using AD credentials. I've attempted multiple databases with various AD accounts.
[WARNING] [health.py] com.microsoft.sqlserver.jdbc.SQLServerException:Login failed for user 'domain\user'
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