Hi @Leo,
Welcome to Microsoft Q&A Platform. Thank you for reaching out & hope you are doing well.
We understand that you are trying to configure application gateway to perform URL redirects but when you try to access https://leo.test.ca/open/ you get redirected to https://tod.test.ca/important/breach//open/ rather than expected https://tod.test.ca/important/breach/ . and is causing issues.
This is expected when the "Include Path" option is enabled in your routing rule as below:
To fix this issue, please disable the "Include Path" option in your routing rule.
Kindly let us know if the above helps or you need further assistance on this issue.
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Regards,
Sai Prasanna.