On 13/05/20 00:34 -0400, Viktor Dukhovni wrote:
an SSL_ERROR_WANT_READ.  You need to try an updated OpenSSL.

Thanks for your insights. I'm trying new things to try to improve my
understanding of the issue.

I juggled around some versions. Bumped to libssl 1.1.1g, restarted
postfix, problem persisted. I also went to postfix 3.5.1 (out of
curiosity, after downgrading back to libssl 1.1.1d) to no avail.

I'm not experiencing any other issues (that I know of) on the machine
in which TLS is used heavily by other programs with greater activity
than postfix. This problem distinctly began immediately after the
upgrade (postfix 3.1.14 -> 3.4.10, libssl 1.1.0l -> 1.1.1d). This is not
to say that the issue is definitely with postfix, just to give more
information.

The pattern in which an email fails due to this issue, and then succeeds
upon immediately being resent is most perplexing. This is repeatable and
suggests that there's some state persisting somewhere.

Further, I just tried sending an email from one address via a web-based
client (it failed) and immediately sending from my normal MUA, to try to
isolate where that state persistence might be. It failed on both,
*however*, I realized that I had forgotten to change my MUA's port back
to 587 (from 588). I changed it to 587, and repeated this test, and to
my surprise, the web-based client failed but the MUA succeeded.

It seems like one fix, which is beyond ugly, could be to set up an email
to be sent every 5 seconds through the mail server to keep the "TLS
warning" state warm, allowing real emails to get through via TLS on
their first attempt. As not every mail server immediately retries not
over TLS upon a TLS failure, this issue is impacting delivery to a
non-insignificant extent.

Alexander

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