SmtpException Triage Report For Dotnet Runtime Issue 117963

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This report is specifically for issue #117963, focusing on networking issues within the dotnet/runtime repository. It's brought to you by MihuBot (version 7cce3b), so if you spot any quirks, ping MihaZupan. Let's dive in!

dotnet/runtime#117963: System.Net.Mail.Tests.SmtpClientTlsTest_Send.AuthenticationException_Propagates failure: expected typeof(System.Security.Authentication.AuthenticationException), actual typeof(System.Net.Mail.SmtpException) by elinor-fung
[Tool] Searching for SmtpClientTlsTest_Send.AuthenticationException_Propagates SmtpException, System.Net.Mail.Tests.SmtpClientTlsTest_Send.AuthenticationException_Propagates, SmtpClientTlsTest AuthenticationException SmtpException, System.Net.Mail.SmtpException instead of System.Security.Authentication.AuthenticationException, SmtpClientTlsTest SendMail exception type (IncludeOpen=True, IncludeClosed=True, IncludeIssues=True, IncludePullRequests=True, Repository=dotnet/runtime)
[Tool] Found 56 issues, 101 comments, 56 returned results (9505 ms)

Here are the most relevant related issues and discussions for issue #117963 ("System.Net.Mail.Tests.SmtpClientTlsTest_Send.AuthenticationException_Propagates failure: expected typeof(System.Security.Authentication.AuthenticationException), actual typeof(System.Net.Mail.SmtpException"):

1. Issue #25885 (April 2018) - Unhandled Exception: System.Net.Mail.SmtpException On Linux

Let's kick things off with Issue #25885 from April 2018, which sheds light on an Unhandled Exception: System.Net.Mail.SmtpException popping up on Linux. This issue delves deep into how SmtpClient.Send can throw an System.Net.Mail.SmtpException, acting like a wrapper for lower-level exceptions. Think of it as the big box that hides the smaller, more specific boxes inside, such as System.ComponentModel.Win32Exception or System.Security.Authentication.AuthenticationException. This is particularly noticeable on Linux when authentication mechanisms like GSSAPI or NTLM throw a fit. 😫

The discussion revolves around several key points:

  • Platform Exception Differences: The types of exceptions you might encounter can vary wildly between different platforms. It’s like trying to order the same dish in two different countries – you might get something similar, but there’ll be a twist!
  • Authentication Scheme Selection: The system picks the strongest authentication scheme it can find, but if that one fails, it doesn't gracefully fall back to weaker ones. It’s like going for the gold and skipping the silver and bronze altogether.
  • Workarounds: There are workarounds, such as forcing a specific authentication scheme using CredentialCache to make it use LOGIN. Think of it as manually setting the GPS to avoid a route the system thinks is best but isn’t.
  • Internal Framework Hacks: Messing with the authentication module order can be risky business. It's like trying to rewire your car’s engine while driving – probably not the best idea. 😬
  • SmtpClient's Wrapping Habit: The general rule is that SmtpClient loves to wrap most errors in SmtpException, which can sometimes hide the real culprit behind the scenes. It’s like getting a present wrapped in layers of boxes – you gotta unwrap them all to see what's inside.

Relevance:

This issue is directly related to the test in question, which anticipates an AuthenticationException but instead gets an SmtpException. The discussion confirms that, yep, SmtpException is the public API's contract, and the inner exception is where the more specific cause (like our friend AuthenticationException) chills out. This behavior isn't a bug; it’s a feature! 😎 It's a known design choice, and knowing is half the battle!

2. Issue #28333 (January 2019) - SMTP send throws AuthenticationException on Linux

Next up, we have Issue #28333 from January 2019, another adventure where SMTP sending on Linux throws an AuthenticationException. Sometimes, though, it's wrapped snuggly inside an SmtpException. The gang's all here!

The discussion hits these highlights:

  • Platform Differences: Again, we see those pesky platform differences in how exceptions propagate. It's like the same story told with different accents.
  • Inner Exception Importance: Always check those inner exceptions! They're the unsung heroes revealing the true story behind the error. 🕵️‍♀️
  • Certificate Validation: Certificate validation and platform-specific SSL/TLS handling play a huge role. It’s like making sure you have the right visa for the country you're visiting – no visa, no entry!

Relevance:

Once again, the SmtpException shows up as the outer wrapper, with the real drama (like our AuthenticationException) playing out as the inner exception. This perfectly mirrors the test failure in #117963. It’s like déjà vu, but in a helpful, troubleshooting kind of way!

3. Issue #117925 (July 2025) - System.Net.Mail.Tests.SmtpClientTlsTest_SendMailAsync.AuthenticationException_Propagates timeout

Zooming into the future (well, kinda – July 2025), we find Issue #117925. This is a recent issue about a related test, SmtpClientTlsTest_SendMailAsync.AuthenticationException_Propagates, timing out on Android. Even though it's not exactly the same failure we're tackling, it does point out that the AuthenticationException_Propagates tests are a bit fragile and can act differently depending on the platform or test environment. It’s like a sensitive artist – needs the perfect conditions to perform!

4. Issue #51260 (April 2021) - System.net.mail.SmtpClient fails to send mail from server having NTLM authentication

Hopping back to April 2021, Issue #51260 surfaces. This one digs into authentication failures with SmtpClient on Linux, including the need for the gss-ntlmssp package (try saying that five times fast!) and the types of exceptions that get thrown. Surprise, surprise – authentication failures often show up as SmtpException, with the real dirt in the inner exception. 😮

5. Issue #46953 (December 2020) - SmtpClient not sending auth

In December 2020, Issue #46953 pops up, discussing authentication problems with SmtpClient after upgrading to .NET 5.0. This also brings up the general deprecation of SmtpClient in favor of MailKit (something to keep in mind!). It reiterates that SmtpException is the main exception type for failures. It's like the old guard stepping aside for the new kid on the block, but still making sure the rules are followed.

6. Issue #19436 (November 2016) - SmtpClient NTLM and Kerberos testing

Rewinding way back to November 2016, we hit Issue #19436. This one’s about beefing up authentication tests for SmtpClient, particularly NTLM and Kerberos. It's super relevant for understanding the test coverage and expectations for how exceptions should be propagated. Think of it as the blueprint for making sure all the security features are working as advertised.

7. PR #287 (November 2019) - SmtpClient SendMailAsync with CancellationToken API implementation

Lastly, we have PR #287 from November 2019. This Pull Request, and the discussions surrounding it, mention test failures where SmtpException gets thrown because of authentication issues. It highlights how the test infrastructure checks for the correct exception type. It's like the quality control check before the product hits the shelves.

Key Takeaways

Alright, guys, let's distill all this info into some key takeaways. 🧠

  • SmtpClient wraps most errors in SmtpException:

    The public API contract for SmtpClient is to throw SmtpException for most hiccups, with the real reason (like AuthenticationException) tucked away as the inner exception. This isn’t a bug; it’s by design and has been discussed a lot. It's like a well-documented quirk!

  • Test expectations may be too strict:

    Tests expecting a specific exception type (like our buddy AuthenticationException) might fail if the implementation wraps it in SmtpException. The savvy move? Check the inner exception! It’s like reading between the lines to get the full picture.

  • Platform differences:

    Ah, those platform differences strike again! How exceptions behave can vary between Windows and Linux, and even across different authentication mechanisms. It's like navigating different dialects of the same language.

  • Known and recurring issue:

    This pattern of exception wrapping is well-known and has been a topic of conversation for years. This isn't a brand-new mystery; it’s a recurring theme in the SmtpClient saga.

Recommendation

So, what's the verdict for issue #117963? 🤔 The test should probably be updated to accept SmtpException and then peek inside its InnerException for AuthenticationException, instead of expecting AuthenticationException right off the bat. This lines up with how the API is supposed to work and fits snugly with all the discussions we've seen above. It’s like adjusting the recipe to match the ingredients we have on hand.

References

Here's a handy list of all the issues and PRs we've chatted about:

If you need a deeper dive into any of these or want to cross-reference something else, just give the word! 🗣️ Let’s keep those .NET runtimes running smoothly! 🚀