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Eudora's TLS/SSL support does not support conical names, nor does it know about some of the new Certificate Authorities that now exist. Conical Names: It used to be that if you issues an SSL certificate, you could only issue it to one domain name, and you had to dedicate an IP address to that domain name. The functionality wasn't really built into the SSL/TLS standard until about 10 years ago, and really wasn't widely supported until about 5 years ago. Services like Microsoft's Office 365 have thousands of domains hosted by one IP address. They use a single SSL certificate for the domains hosted on that IP, and list all the domains in the conical field in order for everything to work right. Eudora does not support this function and only "sees" the first domain name on the certificate. If it does not match the URL/Server Name that was entered, the client will reject the connection. With new CAs -- every year new root Certificates are added to the "realm of trust", either because old ones expire (or get close to expiring), or there are new companies out there that are issuing Certificates. For example, if you bought an SSL certificate in 1996, it was signed by the root "Network Solutions" certificate they used for all their customers. That certificate was valid until 2011. If you were to buy a new SSL certificate today, it would be signed by "User Trust d.b.a Network Solutions III", which is valid until 2035 (or something like that). The problem is that clients like Eudora didn't leverage the operating system to know about these new root certificates and instead baked them into the program. Any certificates that were issued utilizing a new root since Eudora last updated their internal list won't be listed as valid until you import those certificates manually. Baking in certificates is somewhat common for application developers -- but you tend to see it in apps that are updated regularly (like Mozilla Firefox and Google Chrome). The issue with Eudora connecting with MSU's systems is related to the new CA. Issues connecting Eudora to O365 will be related to both of the above issues. The fix will be to manually import these certificates for both cases -- but do beware that when the certificate is updated (either because it is expired or for some other reason), you will have to manually import and trust the new certificates. This happens transparently for the rest of the world, but since Eudora won't trust these new ones it will have to be done by hand. -Nick ________________________________________ From: David McFarlane [[log in to unmask]] Sent: Thursday, September 24, 2015 11:54 AM To: [log in to unmask] Subject: Re: [MSUNAG] Eudora problem -- solved! Yay! It eventually worked for me too! In my case, I had to go 8 layers deep, with multiple restarts. The final cert from East Lansing goes through 3 different Certificate Authorities, including ones in Ann Arbor and New Jersey. Seems like generally suspicious behavior, Eudora is right to reject this nonsense, shame on all the other clients! This nonsense only took away 1 hour of my work day, with three calls to MSU Help Desk. Still waiting for details on why exactly the upcoming mail system will not work with an ordinary POP3 client like Eudora. I would gladly update to a newer, "supported" POP3 client, as long as it was not Outlook, Thunderbird, or Eudora OSE. Anybody have any ideas? Thanks, -- dkm (replying using Eudora, so my name should definitely show correctly now!) At 9/24/2015 11:30 AM Thursday, STeve Andre' wrote: >Thanks to Chris for this link. It has indeed fixed the problem. The key >to this is remembering the chain here, such that you have to go multiple >levels to fix the problem (trust the cert). > >I thank you all for the help. > >--STeve Andre' > >On 09/24/15 07:32, Chris Wolf wrote: >>This will probably fix the problem: >>http://blog.timeoff.org/rick/2015/09/09/revisiting-eudora-ssl-certificate-fa >>ilures/ >> >>I used this a month ago to fix the same type of certificate problem with >>Comcast servers, and I'll be trying it shortly with the current MSU problem. >> >> >>-----Original Message----- >>From: STeve Andre' [mailto:[log in to unmask]] >>Sent: Thursday, September 24, 2015 12:48 AM >>To: [log in to unmask] >>Subject: [MSUNAG] Eudora problem >> >>So, for my anniversary of starting at MSU, I get a present of Eudora not >>working, owing to a expired certificate. I don't think I have any Eudora >>users working at the moment. >> >>There is a tech base article tb158 which didn't work for me. >> >>Has anyone else crashed into this problem and how was it fixed? >>I can enter what I'm seeing tomorrow. Right now I'm about to fall down. >>;-) >> >>--STeve Andre'