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Phase 28 amissl issue

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Simon Dick edited this page Jun 21, 2026 · 7 revisions

AmiSSL TLS 1.3 close-after-handshake against Cloudflare

Filed: https://github.com/jens-maus/amissl/issues/111 (2026-05-31).

This file keeps the full diagnostic + reproduction recipe alongside the rest of the Phase 28 paper trail so the work doesn't have to be re-derived if the GitHub issue is closed or migrates. Mirror updates to both places when material new evidence comes in.

Upstream response (2026-06-01, Futaura, AmiSSL maintainer)

The original report framed this as an AmiSSL or Cloudflare-specific bug; the maintainer pushed back on that framing:

  1. AmiSSL is OpenSSL. "There are very few differences" between AmiSSL and stock OpenSSL, and "no functional differences between the Amiga-specific AmiSSL v4 and v5 APIs." The fingerprinting / ClientHello speculation below is wrong.

  2. Root cause is processor speed, not Cloudflare strict-fronting. "Broken pipe usually means the processor is too slow" — the server's request-read timeout fires before the Amiga finishes the handshake + writes the request. The maintainer notes that api.github.com closes after 4-5 seconds; example.com is a little longer. The "Cloudflare-specific" pattern is a side effect of who happens to use the shortest timeouts, not a fingerprinting heuristic. Their own sites behind Cloudflare don't time out at modern desktop speeds.

  3. The s_client <T:req.txt reproduction may itself be broken. The maintainer notes that stdin redirection from a file isn't expected to work in their port of s_client: "All output in the tool is native, not using stdio/stdout. So, maybe there is an issue with the input. If you type in s_client, it works fine." For our urequests path the redirection question doesn't apply (we drive SSL_write directly from Python), so the CPU-speed limitation is what bites there.

Practical takeaway for the port: TLS works correctly against hosts whose request-read timeout is generous enough for a 68k CPU to complete the handshake + write the request. Modern edges (Cloudflare, GitHub API, etc.) tighten that window aggressively and the Amiga just can't keep up. Document as a CPU-speed limitation rather than an SSL bug; don't try to "fix" it at the SSL layer.

The "Probable cause (speculative)" section near the bottom of this doc is now known-wrong and kept only for historical context.

Title: openssl s_client post-handshake CONNECTION CLOSED BY SERVER + tls_retry_write_records: Broken pipe against Cloudflare-fronted hosts

Environment

  • AmiSSL 5.27 (amissl_v362.library)
  • AmigaOS 3.x under Amiberry, UAE bsdsocket.library emulation (lib v4.1, NegSize 0x12c — original BSD API, gethostbyname-based DNS, getaddrinfo unavailable)
  • Date: 2026-05-31

Symptom

A clean TLS 1.3 handshake against a Cloudflare-fronted host (e.g. www.example.com) completes successfully with full cert verification, then the server closes the connection before any application data can be sent. The next SSL_write returns EPIPE ("Broken pipe") and recv returns errno 54 (ECONNRESET).

The same trace appears against api.github.com. Direct origins that don't strict-front (e.g. www.python.org) work cleanly.

Reproduction

From an AmigaShell on a machine with AmiSSL installed:

1> Echo "HEAD / HTTP/1.0*NHost: www.example.com*NConnection: close*N*N" >T:req.txt
1> AmiSSL:OpenSSL s_client -connect www.example.com:443 \
       -servername www.example.com -CApath AmiSSL:certs -brief <T:req.txt

Actual output

Connecting to 104.20.23.154
CONNECTION ESTABLISHED
Protocol version: TLSv1.3
Ciphersuite: TLS_AES_256_GCM_SHA384
Peer certificate: CN = example.com
Hash used: SHA256
Signature type: ecdsa_secp256r1_sha256
Verification: OK
Negotiated TLS1.3 group: X25519MLKEM768
CONNECTION CLOSED BY SERVER
4000FFC8:error:80000020:system library:tls_retry_write_records:Broken pipe:../../openssl/ssl/record/methods/tls_common.c:1949:tls_retry_write_records failure

With -verify 2 and full chain output, all four certs return verify return:1 and the handshake reports SSL handshake has read 5051 bytes and written 1626 bytes, Verify return code: 0 (ok).

Expected output

HTTP/1.0 200 OK (or the response Cloudflare normally serves to a plain TLS 1.3 client without ALPN).

Workarounds tried

Flag Result
-groups X25519 (skip post-quantum MLKEM hybrid) same close-after-handshake
-no_ticket (disable session tickets) same close-after-handshake
-tls1_2 (force TLS 1.2) Cloudflare rejects ClientHello: unexpected eof while reading

So this isn't MLKEM-specific, isn't session-ticket-related, and dropping to TLS 1.2 isn't an option (Cloudflare has phased it out for most edge configurations in 2026).

Version bisect across AmiSSL v5

Pinning the OpenAmiSSLTags() APIVersion to each installed v5 sub-version in turn (via the -X sslver=<N> flag added to the MicroPython port for this purpose) shows the failure is consistent across the entire available v5 line:

Library AMISSL_V* APIVersion Result
amissl_v352.library (v5.22, Aug 2025) AMISSL_V352 41 handshake ok, write broken pipe
amissl_v353.library (v5.23, Sep 2025) AMISSL_V353 42 handshake ok, write broken pipe
amissl_v354.library (v5.24, Sep 2025) AMISSL_V354 43 handshake ok, write broken pipe
amissl_v360.library (v5.25, Oct 2025) AMISSL_V360 44 handshake ok, write broken pipe
amissl_v361.library (v5.26, Jan 2026) AMISSL_V361 45 handshake ok, write broken pipe
amissl_v362.library (v5.27, Apr 2026) AMISSL_V362 46 same

So the behaviour is not a v5.27 regression — it has been present continuously across at least 8 months of v5 releases. That points to a structural / fingerprint-shape issue in AmiSSL's TLS 1.3 ClientHello (or its OpenSSL 3.x configuration), not to a specific patch that broke things recently.

What didn't fix it (tried in the wrapper)

Attempt Result
SSL_CTX_set_alpn_protos(ctx, "http/1.1") (advertise ALPN) same close-after-handshake
Switching amiga_ssl_open to OpenAmiSSL() + InitAmiSSL() (v4 init API), keeping the rest of the wrapper unchanged SSL_connect now fails earlier with SSL_ERROR_SYSCALL / EIO — the v4 init evidently doesn't bring along the OpenSSL 3.x provider state that v5 needs for TLS 1.3
SSL_CTX_set_mode(ctx, SSL_MODE_AUTO_RETRY) (transparently retry on post-handshake control records) same close-after-handshake
SSL_CTX_set_ciphersuites(ctx, "TLS_CHACHA20_POLY1305_SHA256") (force a different TLS 1.3 suite than the default TLS_AES_256_GCM_SHA384) same close-after-handshake
Kitchen sink: SSL_OP_ALL | SSL_OP_NO_TICKET + SSL_CTX_set_min/max_proto_version(TLS1_3_VERSION) + SSL_CTX_set_session_cache_mode(SSL_SESS_CACHE_OFF) same close-after-handshake
SSL_get_peer_certificate(ssl); X509_free(...); between SSL_connect and SSL_write (match the canonical AmiSSL test/https.c "settling" sequence) same close-after-handshake
Explicit BIO chain: BIO_f_buffer → BIO_new_socket(fd) on the write side via SSL_set_bio, replacing SSL_set_fd SSL_write now reports success (61 bytes accepted into the buffer), but the next SSL_read returns SYSCALL/EIO. The buffer just defers the symptom — Cloudflare still closes, we just notice it later. Not a real fix.
Pass AmiSSL_UsesOpenSSLStructs, TRUE to OpenAmiSSLTags() instead of FALSE (request the actual OpenSSL struct layouts rather than opaque pointers) same close-after-handshake

The v4 init path produces a different broken state, suggesting the divergence between the two init paths inside AmiSSL is non-trivial — it's possible that v4 init enables an option that v5 init doesn't (default ciphers, extension order, SSL_OP_* flags, etc.) that the server happens to accept.

A useful next investigation would be: instrument both paths to log the OpenSSL SSL_CTX options / cipher list / sigalgs after init returns, and diff. Whatever differs is a good candidate for the actual trigger.

Working comparison

Same s_client invocation against www.python.org:443 completes handshake, writes the request, reads the response, and closes cleanly. So TLS 1.3 itself is fine; what's specific is something about AmiSSL's ClientHello/handshake that Cloudflare-class fronts choose not to follow up on.

Probable cause (speculative)

Cloudflare uses TLS client fingerprinting (JA3/JA4) and aggressively closes connections from clients whose fingerprint matches their bot/abuse heuristics. AmiSSL's ClientHello extension order, advertised groups, or signature algorithms may produce a fingerprint Cloudflare doesn't accept. Worth comparing the AmiSSL ClientHello byte-for-byte against a modern desktop OpenSSL 3.x to spot any divergence (extension ordering, omitted extensions, or differing default lists).

Alternatively, the close could be in response to a specific post-handshake message — a NewSessionTicket the client doesn't ACK properly, a KeyUpdate, or a handshake completion alert AmiSSL doesn't emit in the way modern OpenSSL does.

Update 2026-06-21 — the BIO stream path is more resilient

When asyncio-over-TLS landed, the non-blocking memory-BIO stream path (the one built for ssl_poll) succeeded on HTTPS GETs to both www.python.org (52 KB body) and example.com where the blocking fd path (SSL_set_fd, used by urequests) failed in the same session with OSError(5) / "Broken pipe". The fd path relies on a single blocking SSL_connect; under the Amiga's slow handshakes that gets a broken pipe before completing. The stream path pumps ciphertext itself with proper EAGAIN handling, so it tolerates the slowness.

Lead: routing the blocking urequests client through the stream path too (i.e. make the fd path the exception, not the default) would likely cut the intermittent broken-pipe failures — and may also sidestep the Cloudflare close, since we control the read/close sequencing rather than leaving it to SSL_set_fd's socket I/O.

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