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Our business-critical internal software suite was written in Pascal as a temporary solution and has been unmaintained for almost 20 years. It transmits cleartext usernames and passwords as the URI components of GET requests. They also use a single decade-old Excel file to store vital statistics. A key part of the workflow involves an Excel file with a macro that processes an HTML document from the clipboard.
I offered them a better solution, which was rejected because the downtime and the minimal training would be more costly than working around the current issues.