Eudora 7 Unable to Authorize gmail Acct

[freddy3333]

After modifying the emailproxy.config file with my gmail acct and server info, replacing the default ports with the ones I've been using in Eudora for the past few years, when I attempt to download mail from gmail, instead of an Authorization pop-up, Eudora outputs one of these errors:

SSL Negotiation Failed: Unknown Error
The connection with the server has been lost.

Logging into POP Server, PASS
There has been an error transferring your mail. I said: PASS and then the POP server said: ERR [AUTH] Application-specific password required: https://support.google.com/accounts/answer/185833

Since the email proxy never pops-up an Authorization prompt and the Activity Data indicates "never" next to my email address, I suspect something is still misconfigured.

Two specific things that may be relevant:

1. I'm a bit confused about how to generate or acquire the "client_id" and "client_secret"?
   I did follow these instructions (https://developers.google.com/identity/protocols/oauth2/native-app) to create the two client values, then I added them to the config file. But I got kind of lost on google's client generator tool, so I may've done something wrong. Still, I do have both values saved in a text file.

2. I'm also confused about which ports to use for gmail?
   In addition to the ports I've been using, I also tried the default gmail ports (2993, 2995 & 2465) indicated in the sample emailproxy.config as well as many others above ports 1023 and below 65536....none of which seemed to make a difference.

Screenshots of the port settings and my Eudora settings:

[simonrob]

Your POP and SMTP servers are configured to be the default Gmail ones. This needs to be changed to localhost so that your email client connects to the proxy, rather than direct to Gmail. Related to this, one thing you haven't posted is the log file showing the proxy's output. This is a key element in troubleshooting – see the proxy's readme for more details and tips.

Since you mentioned changing various settings in frustration and may just have forgotten to revert these, it's worth mentioning that I remember a previous Eudora issue that turned out to be it not respecting the ports configured in its settings screens. If you still have problems after changing the server settings it's probably worth reading through that entire issue to see whether there are any similarities. Regardless, the settings screenshot you've posted shows the standard Gmail ports, which is not what the proxy uses by default.

You also posted a screenshot of the proxy's dropdown menu, showing that you've configured new ports below 1,024. This is supported, but you need to make sure this doesn't require extra administrative permissions. It's possible for the proxy to be told by the Operating System that it has succeed in opening a port in this range when in reality it has failed due to the lack of permissions. So, it's safest to use ports above 1,024.

[freddy3333]

Thanks Simon.
The only things I've changed are the ports and my account settings, all of which I took screenshots of BEFORE making any changes, so I was easily able to backtrack my work.

I just changed the ports to 2993, 2995 & 2587 and tried again, but still no go. However, when checking the SSL certificates, I see that the server setting is still pop.gmail.com & the port setting is still 995! I restarted Eudora and checked the port and server settings in Eudora's Settings and they're set correctly. So I don't know why they're still showing the old settings in the SSL section??

Attached is a zipped copy of the log.
Thanks again, Simon!

emailproxy.zip

[simonrob]

See this comment in the other issue I referenced previously – it talks about oddities in settings and workarounds for them.

The zip file you posted is empty/invalid...

[freddy3333]

Not sure why the zip failed, but here's another that I just tested OK.
emailproxy.zip

[freddy3333]

See this comment in the other issue I referenced previously – it talks about oddities in settings and workarounds for them.

I'm not sure I understand how chupocro's post relates to solving my issue?? Is my problem related to IMAP (which I don't use)?

[simonrob]

Thanks for the fixed log file. This shows some strange connection behaviour – lots of failures that are ignored by the proxy due to one of the errors caught in this method. If you're happy modifying the code, it would be worth making that method raise the exceptions instead of handling them just so you can see a bit more about what is actually happening. (Since it is in the asyncore package, you may need to override it in the proxy instead).

Re: the older issue – I know very little about Eudora, but wondered whether the same settings idiosyncrasies applied to POP/SMTP. The other thing is that (as discussed in that issue) Eudora is very old software, and could simply not be compatible – this may be the reason for the connection failures. But there are various workarounds discussed there that may well be useful.

[freddy3333]

Simon, I'm sorry, but I've no idea what asyncore is (I'm not a developer), but I'd give it a go if there are specific instructions (for non-developers) somewhere.

Older issue? The only issue I have is getting Eudora to work with gmail's OAuth2.

[GAllen27]

Eudora works fine with this proxy. I've been using the Windows compiled version with O365 email OAuth2 requirement for almost a year now. A huge thank-you to Simon!!!

[freddy3333]

Eudora works fine with this proxy. I've been using the Windows compiled version with O365 email OAuth2 requirement for almost a year now. A huge thank-you to Simon!!!

Thanks for your input!
Based on what I've read, it seems you're not alone in getting it to work with Eudora. Any tips on how you got it to work? Or, did it work out-of-the-box after configuring your O365 login credentials?

[GAllen27]

It's all in the config, for both OAuth2Proxy and Eudora. There is a Eudora OAuth2 Proxy howto writeup for O365 that is long; I posted it here:
https://drive.google.com/file/d/1mrZIyz34WD3UmyvnrOvXovt0blXlzSTa/view?usp=sharing
GMail would be a bit different, but I can't help you there.

[freddy3333]

Many thanks for this! While the puzzle's not been solved yet, I feel like we're nailing down some of the variables I've been concerned/confused about..

It's all in the config, for both OAuth2Proxy and Eudora. There is a Eudora OAuth2 Proxy howto writeup for O365 that is long; I posted it here: https://drive.google.com/file/d/1mrZIyz34WD3UmyvnrOvXovt0blXlzSTa/view?usp=sharing GMail would be a bit different, but I can't help you there.

I see you used the same ports I'd originally used—995 and 587 (and deleted the IMAP section, which I've never used, so I deleted it as well), but set the bracketed numbers as [POP-1995] and [SMTP-1587]. So I reset both Eudora and my emailproxy.config to match your ports (which were the ones I started with and've been using to access gmail for years).

I already had set SSL "Secure Sockets = never", so I'm good there. Otherwise, other than those settings that're particular to O365 vs gmail and my unique "client" codes (which I'm still a bit confused about....so that may be an issue by itself??), I think my Eudora and emailproxy.config settings now match yours. But I'm still NOT getting the authorization prompt and continue to get these bloody connection errors when attempting to login/download email from gmail. Because the error cites "localhost" (with similar results when I change that to "128.0.0.1"), I'm guessing the bottleneck is occurring between Eudora and Simon's proxy???

[freddy3333]

It's all in the config, for both OAuth2Proxy and Eudora. There is a Eudora OAuth2 Proxy howto writeup for O365 that is long; I posted it here: https://drive.google.com/file/d/1mrZIyz34WD3UmyvnrOvXovt0blXlzSTa/view?usp=sharing GMail would be a bit different, but I can't help you there.

I just noticed that, rather than "localhost" as the Eudora POP server setting, you used the outlook.office365.com POP server, which is what I'd originally used (tho', in my case, it was pop.gmail.com). So I tried resetting that back as well...

Unfortunately, it still fails, but Eudora's yin/yang activity icon spun for much longer before popping-up a new/different error:

[freddy3333]

Still not prompted to Authorize or able to access gmail, but I clicked 'Yes' to the SSL Certificate and got another new error that contains "PASS". Headway??

[freddy3333]

Here's a new log file (checked/working)..
emailproxy.zip

[freddy3333]

I apologize for being that guy who keeps posting, but since the author of the article GAllen27 posted got Eudora working, I started over and followed the entire procedure in the section "HOW TO CONFIGURE EMAIL-OAUTH2-PROXY AND EUDORA" from the "Eudora OAuth2 Proxy howto writeup for O365" that GAllen27 posted above.

After following those steps, here's what I did:

1. Configured the emailproxy.config as per the defaults for gmail—SMTP 465, POP 995
2. Configured Eudora as per the section "HOW TO CONFIGURE EMAIL-OAUTH2-PROXY AND EUDORA", with the same port assignments
3. I configured my local Windows firewall to TRUST and permit unfettered network access for "emailproxy.exe"
4. I renamed the original emailproxy.log (so the next run will create a new/shorter log reflecting my result following GAllen27's posted guide)
5. I ran emailproxy.exe as Adminstrator (to eliminate any Windows user permission issue) and enabled Debug mode
6. I opened Eudora and attempted to Check for mail...."localhost" connection refused.
   6a) On a hunch, I closed both emailproxy and Eudora....then, I opened ONLY Eudora and attempted to Check for mail—same error I got with the proxy running: "localhost" connection refused.

Here's the contents of the new emailproxy.log:
2024-05-30 00:50:58,734: Running in a packaged/frozen environment - imported SSL certificates from certifi
2024-05-30 00:50:58,844: Initialising Email OAuth 2.0 Proxy (version 2024-05-25) from config file C:\Users\dt\Desktop\emailproxy-2024-05-25_pyinstaller-Windows\emailproxy.config
2024-05-30 00:50:58,844: Starting POP server at 127.0.0.1:2995 (unsecured) proxying pop.gmail.com:995 (SSL/TLS)
2024-05-30 00:50:58,859: Starting SMTP server at 127.0.0.1:2465 (unsecured) proxying smtp.gmail.com:465 (SSL/TLS)
2024-05-30 00:50:58,859: Initialised Email OAuth 2.0 Proxy - listening for authentication requests. Connect your email client to begin
2024-05-30 00:51:03,907: Setting debug mode: True
2024-05-30 00:51:43,849: Stopping Email OAuth 2.0 Proxy
2024-05-30 00:51:43,958: Stopping POP server at 127.0.0.1:2995 (unsecured) proxying pop.gmail.com:995 (SSL/TLS)
2024-05-30 00:51:43,958: Stopping SMTP server at 127.0.0.1:2465 (unsecured) proxying smtp.gmail.com:465 (SSL/TLS)

So, since Eudora's "localhost" connection is refused regardless of whether the emailproxy is running or not, my gut says the problem is that Eudora's NOT communicating either with "localhost" or the emailproxy. Does that spark any thoughts???