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Can I see a screenshot showing how the original symptom looks like for a technical review?
As no further input gathered against my last clarifying question, I now provide a general answer based on the given description and common situations.
Eudora's certificate problem has been a known issue due to the legacy app's limited support to the latest certificates and modern security protocols. Some fans of Eudora have found some solutions but unfortunately, not all of the third-party solutions are always workable.
Please see the related resource below.
Trusting Certificates in Eudora 7
Eudora server SSL certificate rejected
Eudora and SSL Certificate Failures
However, another approach is to use a modern email program instead of Eudora, such as Mozilla Thunderbird - the most popular free email program supported by the communities.
Just hope these could help.