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net/http over TLS: non-blocking SSLSocket, timeouts, and the context's CAs - #28
Both stages of Docs/net-http-over-tls.md (#25). IronRuby's OpenSSL::SSL::SSLSocket ran on a blocking SslStream. Its read_nonblock, write_nonblock and connect_nonblock never returned :wait_readable/:wait_writable, which are the only paths where net/protocol applies a timeout. So over TLS, read_timeout, write_timeout and the handshake's open_timeout never fired, and a stalled server hung the caller. ca_file, ca_path, cert_store and verify_callback were also ignored.
Non-blocking TLS (stage 2)
OpenSSL::SSL::Transport__ runs every read, write and handshake as one of SslStream's asynchronous operations, at most one of each kind in flight.
read_nonblock, write_nonblock (at most 16 KB handed over at a time) and connect_nonblock start one and answer :wait_readable/:wait_writable while it runs.
read, write and connect wait for one, bounded by read_timeout, write_timeout or the handshake timeout. Running out raises IO::TimeoutError and leaves the transport unusable.
IReadinessHook (Src/Libraries/Builtins/IoReadiness.cs) is a per-RubyIO hook. IO.select, IO#wait* and NIO::Selector ask it before the socket, and it wakes their waiter when its answer may have changed.
The transport is the TCP socket's hook, so a select on SSLSocket#to_io sees an operation finish.
It also sees bytes that SslStream holds but the TCP socket no longer shows. Asking whether a read would return starts that read, and what the read brings waits in a read-ahead (#pending).
SSLSocket#*_nonblock raise SSLErrorWaitReadable/SSLErrorWaitWritable, or answer the symbol with exception: false.
With that, upstream net/protocol applies all three timeouts by itself, unmodified, for Net and for RubyGems' vendored Gem::Net. Stage 1's net/protocol overrides were removed.
Thread#raise or Timeout.timeout during a blocking handshake cancels it, marks the transport broken, and raises the interrupting exception, not an SSLError.
Certificate verification, as CRuby/OpenSSL has it
The context's CAs are trusted through X509ChainTrustMode.CustomRootTrust, and the chain must allow serverAuth, as SslStream's own check does. The hostname check is kept.
verify_callback, as CRuby's ossl_verify_cb_call does it:
It is called once per certificate and error, root first, with an X509::StoreContext.
Only true accepts, and it clears the error.
The first rejection ends the check.
An exception raised by the callback is a rejection with a warning.
OpenSSL::X509 has the standard V_ERR_* constants, with OpenSSL's codes: 18 for a lone self-signed certificate, 9 not yet valid, 10 expired, 26 wrong purpose. Error 26 goes only to the certificate whose own extendedKeyUsage is wrong. Linux's .NET flags every certificate in that chain, which was the first Linux CI failure here.
post_connection_check checks the certificate's names, including IP SANs, and falls back to the common name when there is no subjectAltName.
Also
resolv on Windows asks for win32/resolv. ruby/4.0 has no copy of it, so the 1.9.1 one was loaded, and with it the old DL library and a parse warning on every require "net/http". Src/StdLib/ironruby/win32/resolv.rb now answers from System.Net.NetworkInformation.
socket.rb: an unused rescue variable (another parse warning) is gone.
Initializers.Generated.cs is byte for byte what ClassInitGenerator writes.
Not done: the server side (SSLServer, #accept), so puma over TLS still cannot run.
Testing
NetHttp_Tls1, NetHttp_TlsVerifyCallback1, NetHttp_PlainNoOpenSsl1, NetHttp_GemNetTls1 and Ssl_NonBlocking1 host their own TLS server in C#. It has a CA plus issued, client-auth-only, expired, not-yet-valid and CN-only certificates, and a plain HTTP port. They no longer silence $VERBOSE.
Ssl_NonBlocking1 covers a connect_nonblock loop, read_nonblock with IO.select, the read-ahead, write_nonblock into a server that reads nothing, and NIO::Selector over TLS.
On Windows / .NET 10 the full IronRuby.Tests suite has 0 failures.
Util/net-http-tls-check.rb against the CRuby server reports no failures for http or https, with and without CA=1.
Summary by CodeRabbit
New Features
Added TLS support for HTTP connections, including certificate-chain and hostname verification, custom trust sources, verification callbacks, and configurable connection, read, and write timeouts.
Added nonblocking TLS connection, read, and write operations with readiness support for network polling.
Added TLS timeout support for RubyGems’ bundled HTTP client.
Added Windows DNS and hosts-file information lookup.
Plain HTTP requests no longer require OpenSSL to be loaded in advance.
Documentation
Updated TLS documentation to describe current support and limitations, including that server-side TLS connections are not yet supported.
Stage 1 of Docs/net-http-over-tls.md. IronRuby's SSLSocket is a blocking
SslStream, so net/http's read_timeout, write_timeout and open_timeout (which
upstream applies only after :wait_readable/:wait_writable) never fired over
TLS, and ca_file, ca_path, cert_store and verify_callback were ignored.
- OpenSSL::SSL::Transport__ gets read_timeout=/write_timeout= (SslStream
ReadTimeout/WriteTimeout) and a handshake timeout (AuthenticateAsClientAsync
under a CancellationTokenSource). Running out raises IO::TimeoutError and
leaves the transport unusable.
- Src/StdLib/ironruby/net/protocol.rb loads upstream's file unchanged and
prepends ssl_socket_connect, rbuf_fill and write0 overrides for IronRuby
SSLSockets, mapping IO::TimeoutError to Net::OpenTimeout/ReadTimeout/
WriteTimeout.
- Transport__ validates against the context's self-signed CAs with
X509ChainTrustMode.CustomRootTrust (others in ExtraStore, as Store#verify),
keeps the name check, and lets verify_callback decide, called per
certificate with an X509::StoreContext.
- post_connection_check checks the certificate's names (IP SANs included);
for an IP address, which gets no SNI name, it used to check nothing.
Util/net-http-tls-check.rb against the CRuby server: no failures for http or
https, with and without CA=1. NetHttp_Tls1 hosts its own TLS server.
…stays light
Follow-up to the TLS timeouts and CA settings, from review:
- verify_callback is called once per certificate and error, root first, in
the order OpenSSL meets them, as ossl_verify_cb_call: only true accepts
and clears the error (verify_result is V_OK for a connection that stands),
the first rejection ends the check, and an exception in the callback is a
rejection with a warning instead of an exception out of #connect.
- OpenSSL::X509 has the standard V_ERR_* constants, and the codes follow
OpenSSL: 18 for a lone untrusted self-signed certificate (19 in a chain),
9 not yet valid, 10 expired, 26 the wrong purpose.
- The chain built against the context's CAs requires serverAuth, as
SslStream's own check does: a certificate for client authentication only
is refused.
- Thread#raise or Timeout.timeout during the handshake cancels it, marks the
transport broken, keeps a late certificate check out of Ruby, and raises
the interrupting exception instead of an SSLError.
- post_connection_check matches a certificate without subjectAltName on its
common name, for an IP address too, and answers an empty name with
SSLError.
- The custom X509Chain and the certificate copy are disposed.
- net/protocol's override checks for IronRuby's SSLSocket before naming
OpenSSL, so a plain HTTP request no longer runs net/http's openssl
autoload.
- The doc says that RubyGems' vendored Gem::Net gets none of this.
The test server now has a CA with issued, client-auth-only, expired,
not-yet-valid and CN-only certificates, and a plain HTTP port.
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Files selected for processing: 11
Docs/net-http-over-tls.md
Src/IronRuby.Tests/RubyTests.cs
Src/IronRuby.Tests/Runtime/NetHttpTlsTests.cs
Src/Libraries/Builtins/IoOps.cs
Src/Libraries/Builtins/IoReadiness.cs
Src/Libraries/Nio4r/Nio4r.cs
Src/Libraries/OpenSSL/OpenSSL.cs
Src/StdLib/ironruby/openssl.rb
Src/StdLib/ironruby/openssl/ssl.rb
Src/StdLib/ironruby/socket.rb
Src/StdLib/ironruby/win32/resolv.rb
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Src/IronRuby.Tests/Runtime/NetHttpTlsTests.cs
Src/Libraries/OpenSSL/OpenSSL.cs
Src/StdLib/ironruby/win32/resolv.rb
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Walkthrough
The changes add asynchronous TLS transport operations, certificate verification, IO readiness integration, and runtime coverage. They also add Windows resolver methods and update TLS implementation documentation.
IO readiness checks and NIO selectors now query registered hooks and manage hook waiter registration.
Asynchronous TLS transport Src/Libraries/OpenSSL/OpenSSL.cs
The TLS transport now supports asynchronous handshakes, reads, and writes; configurable timeouts; readiness reporting; read-ahead buffering; and certificate trust validation.
Ruby SSL verification and nonblocking APIs Src/StdLib/ironruby/openssl.rb, Src/StdLib/ironruby/openssl/ssl.rb, Src/StdLib/ironruby/socket.rb
Ruby SSL APIs configure trust sources and verification callbacks, expose verification results, check hostnames, and handle nonblocking operations and timeouts. The socket change removes an unused exception variable.
TLS tests and documentation Src/IronRuby.Tests/RubyTests.cs, Src/IronRuby.Tests/Runtime/NetHttpTlsTests.cs, Docs/net-http-over-tls.md
Runtime tests cover TLS trust, timeouts, callbacks, hostname checks, readiness, vendored Gem::Net, and plain HTTP. Documentation describes the implemented behavior and notes that SSLServer and accept remain unimplemented.
Windows Resolver Support
Layer / File(s)
Summary
Windows resolver information Src/StdLib/ironruby/win32/resolv.rb
Win32::Resolv adds hosts-file path lookup and retrieval of DNS search domains and name servers from active network interfaces.
sequenceDiagram
participant SSLSocket
participant Transport
participant SslStream
participant IOSelect as IO.select
SSLSocket->>Transport: Start nonblocking handshake
Transport->>SslStream: Begin asynchronous authentication
Transport-->>SSLSocket: Return wait_readable while handshake runs
IOSelect->>Transport: Query socket readiness hook
Transport-->>IOSelect: Report handshake or read readiness
Loading
Merge Risk: Minimal · previous review 456f4
The Windows resolver honors a configured DNS search list, and the non-blocking TLS write test now waits for real backpressure before asserting. No actionable merge-blocking issue remains.
Pre-merge checks: 4 · 1
Failed checks: 1 warning
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Docstring coverage is 53.41% which is insufficient. The required threshold is 80.00%. Docstring coverage is scoped to functions touched by this diff. Documentation-only edits and deletions within surv…
Write docstrings for the functions missing them to satisfy the coverage threshold.
Passed checks: 4 passed
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Title check
The title names the main thrust of the changeset. The PR adds non-blocking and timeout-bounded SSLSocket/Transport operations, and it changes certificate verification so the context's CA certificates …
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The title names the main thrust of the changeset. The PR adds non-blocking and timeout-bounded SSLSocket/Transport operations, and it changes certificate verification so the context's CA certificates are used. The title does not mention the readiness hook in IO.select/NIO, the Windows resolv replacement, or the new tests, but those are secondary to the title's focus. The title is specific and concise. It is 74 characters and 10 words, which is acceptable for a title.
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Docstring coverage is 53.41% which is insufficient. The required threshold is 80.00%. Docstring coverage is scoped to functions touched by this diff. Documentation-only edits and deletions within surviving functions are included; unchanged diff context and fully deleted functions are excluded. Analyzed 88 functions across 10 files.
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…ithout DL
- The net/protocol overrides move to ironruby/net_tls.rb and work for any
copy of net/protocol. RubyGems' vendored Gem::Net is loaded with
require_relative, so SSLSocket#initialize installs them once it exists;
Gem::Net::HTTP#connect makes the socket before ssl_socket_connect, so the
first handshake is covered too.
- Linux's .NET flags every certificate of a chain whose leaf is for the
wrong purpose; V_ERR_INVALID_PURPOSE now goes only to a certificate whose
own extendedKeyUsage does not allow server authentication, as OpenSSL
reports it. This was the Linux CI failure in NetHttp_TlsVerifyCallback1.
- Store#verify reports 20 again for a chain status with no OpenSSL
equivalent, as before.
- resolv asks for win32/resolv on Windows. ruby/4.0 has no copy (CRuby's is
built with its C extension), so the 1.9.1 one was loaded, and with it the
old DL library and a parse warning. Src/StdLib/ironruby/win32/resolv.rb
answers get_hosts_path and get_resolv_info from
System.Net.NetworkInformation.
- socket.rb: drop an unused rescue variable (a parse warning on every
require of net/http). The TLS tests no longer silence $VERBOSE.
- Initializers.Generated.cs is now byte for byte what ClassInitGenerator
writes (the hand-written registrations lacked its trailing spaces).
IronRuby's SSLSocket answered every *_nonblock call by blocking, which net/protocol
took as "the data is here" and which stage 1 papered over with overrides that fed
net/protocol's timeouts to the blocking calls. Now the calls are what MRI's are:
- Transport__ runs every read, write and handshake as one of SslStream's
asynchronous operations, at most one of each kind in flight. read_nonblock,
write_nonblock (at most 16 KB handed over at a time) and connect_nonblock start
one and answer :wait_readable / :wait_writable while it runs; read, write and
connect start one or take over the one in flight and wait for it, at most
read_timeout, write_timeout or the handshake timeout.
- IReadinessHook (IoReadiness.cs): a per-RubyIO hook that IO.select, IO#wait*
and NIO::Selector ask before the socket, and that signals their
ReadinessWaiter when its answer may have changed. The transport is the TCP
socket's hook, so a select on SSLSocket#to_io sees an operation finish, and
sees bytes SslStream holds that the TCP socket no longer shows: asking whether
a read would return starts that read, and what it brings waits in a read-ahead
that #pending counts.
- SSLSocket#read_nonblock, #write_nonblock and #connect_nonblock raise
SSLErrorWaitReadable / SSLErrorWaitWritable, or answer the symbol with
exception: false.
- The net/protocol overrides (Src/StdLib/ironruby/net/protocol.rb,
ironruby/net_tls.rb) are gone: upstream's own waits now apply open_timeout,
read_timeout and write_timeout, for Net and RubyGems' Gem::Net alike.
Ssl_NonBlocking1 drives a connect_nonblock loop, read_nonblock with IO.select,
the read-ahead, write_nonblock into a server that reads nothing, and
NIO::Selector over TLS. The existing TLS tests pass unchanged against upstream
net/protocol. Util/net-http-tls-check.rb: no failures, with and without CA=1.
Largo
changed the title
net/http over TLS: timeouts, and the context's CAs
net/http over TLS: non-blocking SSLSocket, timeouts, and the context's CAs
Oct 27, 2026
Largo
pushed a commit
that referenced
this pull request
Oct 27, 2026
ironruby/win32/resolv.rb now takes #28's version verbatim, which
ran in that PR's CI, so the two PRs add the same file.
Co-Authored-By: Claude Opus 5.5 <noreply@anthropic.com>
Claude-Session: https://claude.ai/code/session_01KPwZf7csSRV3oAVQ31sLDS
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Actionable comments posted: 3
🪄 Fix comments: Fix CodeRabbit comments on this PR
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Inline comments:
Review comments at @Src/IronRuby.Tests/Runtime/NetHttpTlsTests.cs:
- Around line 329-335: Update the write loop in Ssl_NonBlocking1 so
:wait_writable does not immediately count as backpressure: wait for writability
with a timeout, continue writing if the socket becomes writable, and stop only
when that wait times out. Preserve the existing output assertions so they verify
the timed-out state.
Review comments at @Src/Libraries/OpenSSL/OpenSSL.cs:
- Around line 811-828: Update FinishConnect’s handshake failure path to set
_broken under _sync before rethrowing the callback or SSL error, so subsequent
operations are rejected by CheckUsable.
Review comments at @Src/StdLib/ironruby/win32/resolv.rb:
- Around line 32-33: Update the Windows resolver logic that populates search so
it reads the configured DNS SearchList through a supported registry API and uses
its entries in their configured order when present, overriding the
machine-domain and interface DnsSuffix fallbacks.
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Reviewing files that changed from the base of the PR and between 7cae2c0 and 7f70634.
Files ignored due to path filters: 1
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Files selected for processing: 11
Docs/net-http-over-tls.md
Src/IronRuby.Tests/RubyTests.cs
Src/IronRuby.Tests/Runtime/NetHttpTlsTests.cs
Src/Libraries/Builtins/IoOps.cs
Src/Libraries/Builtins/IoReadiness.cs
Src/Libraries/Nio4r/Nio4r.cs
Src/Libraries/OpenSSL/OpenSSL.cs
Src/StdLib/ironruby/openssl.rb
Src/StdLib/ironruby/openssl/ssl.rb
Src/StdLib/ironruby/socket.rb
Src/StdLib/ironruby/win32/resolv.rb
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…SearchList
From review and the Windows CI run of 7f70634:
- Ssl_NonBlocking1 took the first :wait_writable for a full buffer. On
Windows a NetworkStream write is overlapped I/O and is in flight almost
every time, so the write finished within the following select and the
socket was writable again. The loop now waits for writability and stops
only when that wait runs out.
- A failed handshake left the unauthenticated SslStream in place, so a
second #connect or #connect_nonblock found it and reported the socket
connected. FinishConnect now marks the transport broken. NetHttp_Tls1
connects twice to a server the context does not trust.
- Win32::Resolv.get_resolv_info uses the configured domain suffix search
list (Tcpip\Parameters SearchList) alone and in its order when there is
one, as Windows and CRuby's win32/resolv do; otherwise the machine's
domain and the interfaces' connection-specific suffixes.
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Largo
changed the title
![coderabbitai[bot]](https://avatars.githubusercontent.com/in/347564?s=60&v=4){kind=small}
Both stages of
Docs/net-http-over-tls.md(#25). IronRuby'sOpenSSL::SSL::SSLSocketran on a blockingSslStream. Itsread_nonblock,write_nonblockandconnect_nonblocknever returned:wait_readable/:wait_writable, which are the only paths wherenet/protocolapplies a timeout. So over TLS,read_timeout,write_timeoutand the handshake'sopen_timeoutnever fired, and a stalled server hung the caller.ca_file,ca_path,cert_storeandverify_callbackwere also ignored.Non-blocking TLS (stage 2)
OpenSSL::SSL::Transport__runs every read, write and handshake as one of SslStream's asynchronous operations, at most one of each kind in flight.read_nonblock,write_nonblock(at most 16 KB handed over at a time) andconnect_nonblockstart one and answer:wait_readable/:wait_writablewhile it runs.read,writeandconnectwait for one, bounded byread_timeout,write_timeoutor the handshake timeout. Running out raisesIO::TimeoutErrorand leaves the transport unusable.IReadinessHook(Src/Libraries/Builtins/IoReadiness.cs) is a per-RubyIOhook.IO.select,IO#wait*andNIO::Selectorask it before the socket, and it wakes their waiter when its answer may have changed.SSLSocket#to_iosees an operation finish.#pending).SSLSocket#*_nonblockraiseSSLErrorWaitReadable/SSLErrorWaitWritable, or answer the symbol withexception: false.net/protocolapplies all three timeouts by itself, unmodified, forNetand for RubyGems' vendoredGem::Net. Stage 1's net/protocol overrides were removed.Thread#raiseorTimeout.timeoutduring a blocking handshake cancels it, marks the transport broken, and raises the interrupting exception, not anSSLError.Certificate verification, as CRuby/OpenSSL has it
X509ChainTrustMode.CustomRootTrust, and the chain must allow serverAuth, as SslStream's own check does. The hostname check is kept.verify_callback, as CRuby'sossl_verify_cb_calldoes it:X509::StoreContext.trueaccepts, and it clears the error.OpenSSL::X509has the standardV_ERR_*constants, with OpenSSL's codes: 18 for a lone self-signed certificate, 9 not yet valid, 10 expired, 26 wrong purpose. Error 26 goes only to the certificate whose own extendedKeyUsage is wrong. Linux's .NET flags every certificate in that chain, which was the first Linux CI failure here.post_connection_checkchecks the certificate's names, including IP SANs, and falls back to the common name when there is no subjectAltName.Also
resolvon Windows asks forwin32/resolv.ruby/4.0has no copy of it, so the 1.9.1 one was loaded, and with it the old DL library and a parse warning on everyrequire "net/http".Src/StdLib/ironruby/win32/resolv.rbnow answers fromSystem.Net.NetworkInformation.socket.rb: an unused rescue variable (another parse warning) is gone.Initializers.Generated.csis byte for byte what ClassInitGenerator writes.Not done: the server side (
SSLServer,#accept), so puma over TLS still cannot run.Testing
NetHttp_Tls1,NetHttp_TlsVerifyCallback1,NetHttp_PlainNoOpenSsl1,NetHttp_GemNetTls1andSsl_NonBlocking1host their own TLS server in C#. It has a CA plus issued, client-auth-only, expired, not-yet-valid and CN-only certificates, and a plain HTTP port. They no longer silence$VERBOSE.Ssl_NonBlocking1covers aconnect_nonblockloop,read_nonblockwithIO.select, the read-ahead,write_nonblockinto a server that reads nothing, andNIO::Selectorover TLS.Util/net-http-tls-check.rbagainst the CRuby server reports no failures for http or https, with and withoutCA=1.Summary by CodeRabbit