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Hi mbellas,
Thanks for reaching out to Redgate Support. Support for version 20 of SSMS was added in March of this year for SQL Prompt. (Version 10.14.11.7894) Could I have you confirm the version of Prompt that you have installed by clicking on SQL Prompt > Help > About SQL Prompt in SSMS?
Additionally, I would like to gather your SQL Prompt log to confirm the connection errors you are mentioning. (File Link HERE) Could you select SQL Prompt > Help > Enable Verbose Logging and then replicate the connection error and afterwards select SQL Prompt > Help > Locate Log Files and attach them to the File Link I left above?
Best Regards,
Christian Perez
Product Support Engineer
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As a workaround I have to use the "Trust server certificate" option.