fix(proxy): build SSL contexts for custom CA bundles#1134
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Signed-off-by: Mark Phelps <209477+markphelps@users.noreply.github.com>
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Reviewed the custom CA SSLContext change. Replacement vs additive semantics are preserved while passing httpx a context that can relax only VERIFY_X509_STRICT for operator-provided bundles, with tests covering priority and strict-flag handling. CI is green.
JerrettDavis
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Re-reviewed the current head after the main merge. The SSL context change remains scoped: custom CA bundles still verify certificates and hostnames, while only VERIFY_X509_STRICT is relaxed for operator-provided bundles. The tests cover replacement/additive semantics and env priority, and CI is green.
…#1134) ## Description Build explicit `ssl.SSLContext` objects for custom CA bundles configured through `SSL_CERT_FILE` and `REQUESTS_CA_BUNDLE`. Python 3.13 / newer OpenSSL can reject some enterprise/private PKI roots that platform TLS stacks accept, for example roots without a `keyUsage` extension. The new custom-CA contexts keep certificate verification enabled while clearing only `ssl.VERIFY_X509_STRICT`. Closes # ## Type of Change - [x] Bug fix (non-breaking change that fixes an issue) - [ ] New feature (non-breaking change that adds functionality) - [ ] Breaking change (fix or feature that would cause existing functionality to change) - [ ] Documentation update - [ ] Performance improvement - [ ] Code refactoring (no functional changes) ## Changes Made - Build replacement `SSLContext` objects for `SSL_CERT_FILE` and `REQUESTS_CA_BUNDLE` instead of passing raw CA bundle paths to httpx. - Clear only `ssl.VERIFY_X509_STRICT` for operator-provided custom CA contexts; certificate verification, hostname verification, expiry checks, and chain validation stay enabled. - Preserve `NODE_EXTRA_CA_CERTS` additive behavior by loading the extra CA bundle on top of the default/system trust store. - Update existing SSL context tests for replacement CA contexts, env-var priority, missing-path fallthrough, and strict-mode relaxation. - Add an Unreleased changelog entry for the proxy bug fix. ## Testing - [x] Unit tests pass (`pytest`) - [x] Linting passes (`ruff check .`) - [ ] Type checking passes (`mypy headroom`) - [x] New tests added for new functionality - [x] Manual testing performed ### Test Output ```text $ PYTHONPATH=. .venv/bin/python -m pytest tests/test_ssl_context.py -q collected 12 items tests/test_ssl_context.py ............ [100%] 12 passed, 1 warning in 0.11s ``` ```text $ uv tool run ruff check headroom/proxy/ssl_context.py tests/test_ssl_context.py CHANGELOG.md All checks passed! $ uv tool run ruff format --check headroom/proxy/ssl_context.py tests/test_ssl_context.py 2 files already formatted ``` ## Real Behavior Proof - Environment: macOS, Python 3.13.2, Headroom checkout on this branch, `SSL_CERT_FILE` / `REQUESTS_CA_BUNDLE` / `NODE_EXTRA_CA_CERTS` pointed at an enterprise/private PKI CA bundle. Upstream HTTPS endpoint name is redacted. - Exact command / steps: Ran a Python smoke script that imports `headroom.proxy.ssl_context.find_ca_bundle()`, passes the returned verifier into `httpx.AsyncClient(verify=...)`, and performs a GET against the enterprise HTTPS endpoint that previously failed with OpenSSL strict verification. - Observed result: The request used an `SSLContext`, strict X.509 verification was disabled for that custom CA context, and the request reached the upstream HTTP response: ```text verify_type SSLContext strict_enabled False status 302 ``` - Not tested: Full `uv run pytest`, `uv sync --extra dev`, and `mypy headroom` in this local environment. The editable build currently fails before tests run because Cargo's `ort-sys` build script cannot download ORT prebuilt binaries due an unrelated local certificate verification error against the ORT CDN. No dependency or lockfile changes are included in this PR. ## Review Readiness - [x] I have performed a self-review - [x] This PR is ready for human review ## Checklist - [x] My code follows the project's style guidelines - [x] I have performed a self-review of my code - [x] I have commented my code, particularly in hard-to-understand areas - [ ] I have made corresponding changes to the documentation - [x] My changes generate no new warnings - [x] I have added tests that prove my fix is effective or that my feature works - [x] New and existing unit tests pass locally with my changes - [x] I have updated the CHANGELOG.md if applicable ## Screenshots (if applicable) N/A. ## Additional Notes No dependencies or lockfiles changed. Documentation is unchanged because this is a bug fix to existing custom CA environment-variable behavior rather than a new user-facing configuration surface. Signed-off-by: Mark Phelps <209477+markphelps@users.noreply.github.com> Co-authored-by: JD Davis <mxjerrett@gmail.com>
🤖 I have created a release *beep* *boop* --- <details><summary>0.28.0</summary> ## [0.28.0](v0.27.0...v0.28.0) (2026-06-29) ### Features * add --disable-kompress-fallback to restore legacy PASSTHROUGH fallback ([#1185](#1185)) ([f309244](f309244)) * add first-class OpenCode support (wrap, learn, mcp install) ([#559](#559)) ([91cd210](91cd210)) * add HEADROOM_KEEPALIVE_EXPIRY to keep upstream connections warm ([#1124](#1124)) ([85786b3](85786b3)) * **azure-foundry:** derive upstream URL from ANTHROPIC_FOUNDRY_RESOURCE ([#1138](#1138)) ([e5031b0](e5031b0)) * **cache:** attribute prompt-cache misses to TTL lapse vs prefix change ([#1313](#1313)) ([#1343](#1343)) ([4658721](4658721)) * **code:** add Perl support to code-aware compressor ([#1125](#1125)) ([f39858c](f39858c)) * headroom wrap opencode / unwrap opencode CLI ([#1105](#1105)) ([b4571cc](b4571cc)) * **learn:** weight loops in Headroom Learn + RTK-loop eval ([#1160](#1160)) ([14e8dc4](14e8dc4)) * **learn:** write per-project learnings to CLAUDE.local.md by default ([#1115](#1115)) ([ced75e4](ced75e4)) * **proxy:** add request timeout config ([#738](#738)) ([c0745d4](c0745d4)) * **proxy:** pilot hardening — inbound auth, security headers, audit log, air-gap switch ([#1537](#1537)) ([546ab55](546ab55)) * **proxy:** support glob patterns in exclude_tools ([#870](#870)) ([#1259](#1259)) ([a2159c0](a2159c0)) * **read-maturation:** activity-based hold-back Read maturation (Mechanism B) ([#1068](#1068)) ([723b80c](723b80c)) * **savings:** durable savings ledger + headroom savings command ([#1127](#1127)) ([978ffa0](978ffa0)) * **wrap:** add --1m to preserve the 1M context window on wrap claude ([#1158](#1158)) ([#1351](#1351)) ([b50d9c1](b50d9c1)) * **wrap:** make tokensave the primary coding-task compressor, Serena the backup ([#1230](#1230)) ([dca9853](dca9853)) ### Bug Fixes * **agent-evals:** Phase 0 — coding-agent accuracy A/B framework ([#1037](#1037)) ([84f9871](84f9871)) * **agno:** tolerate streaming tool-call SDK objects in parser ([#1312](#1312)) ([#1336](#1336)) ([5986c22](5986c22)) * **bedrock:** add boto3 1.41 + CRT for aws login credentials ([#1486](#1486)) ([4db3bc9](4db3bc9)) * bump codebase-memory-mcp to v0.8.1 ([#1284](#1284)) ([530318b](530318b)) * **ccr:** make headroom_retrieve a hash-only full-content lookup ([#1532](#1532)) ([c2fc4d3](c2fc4d3)) * **ccr:** propagate --no-ccr-marker flag to all compressors ([#1022](#1022)) ([#1197](#1197)) ([0c9b42a](0c9b42a)) * **ccr:** skip Anthropic marker emission when tool injection is deferred ([#1273](#1273)) ([2cae13d](2cae13d)) * **ci:** extend gitleaks allowlist to cover test fixtures + verified examples ([#1539](#1539)) ([d2565a6](d2565a6)) * **ci:** guarantee model present in test shards to end cache-miss flakiness ([#1399](#1399)) ([2e29c72](2e29c72)) * **ci:** normalize Windows CRLF line endings in PR governance script ([#1012](#1012)) ([5194388](5194388)) * **cli:** add explicit UTF-8 encoding to file I/O in wrap commands ([#1126](#1126)) ([#1164](#1164)) ([a0cb798](a0cb798)) * **cli:** fall back gracefully when embedding-server sidecar is absent ([#1206](#1206)) ([38f1404](38f1404)) * **cli:** harden all CLI surfaces + fix docs accuracy ([#1491](#1491)) ([bd76235](bd76235)) * **cli:** wire --http2/--no-http2 (HEADROOM_HTTP2) into proxy command ([#1373](#1373)) ([e06b616](e06b616)) * **cli:** wire --rpm/--tpm and HEADROOM_RPM/HEADROOM_TPM to the Click proxy command ([#1375](#1375)) ([8aab8f2](8aab8f2)) * **code:** slice tree-sitter byte offsets as UTF-8 ([#1332](#1332)) ([8238402](8238402)) * **code:** validate Python compressed syntax ([#1302](#1302)) ([cbd361d](cbd361d)) * **code:** verify a real parse in tree-sitter availability check ([#1231](#1231)) ([#1299](#1299)) ([5e0bb69](5e0bb69)) * **codex:** retag threads on init so Codex Desktop history stays visible ([#961](#961)) ([#1349](#1349)) ([e6bbc40](e6bbc40)) * **codex:** stop pinning Codex memory MCP to one project db ([#1269](#1269)) ([ad7993b](ad7993b)) * **dashboard:** include RTK stats in the historical tab ([#1324](#1324)) ([35939c3](35939c3)) * **deps:** remediate dependency CVEs and publish SBOM ([#1509](#1509)) ([5771a80](5771a80)) * **docker:** persist session history across container revisions ([#1118](#1118)) ([5912d65](5912d65)) * **gemini:** offload compression to the executor ([#1382](#1382)) ([615848e](615848e)) * **gemini:** resolve Google model capabilities through ModelRegistry ([#1276](#1276)) ([17ecad9](17ecad9)) * **install:** guard install_agent_ensure against duplicate runtime spawns ([#1301](#1301)) ([8da0b4e](8da0b4e)) * **install:** repair macOS launchd restart/start lifecycle ([#1290](#1290)) ([da1a397](da1a397)) * **install:** stop duplicating ENTRYPOINT in persistent-docker runtime command ([#833](#833)) ([#1348](#1348)) ([feedead](feedead)) * **io:** use UTF-8 with locale fallback and preserve line endings on config/text I/O ([#1498](#1498)) ([1baa04e](1baa04e)) * **kompress:** hard override keeps must-keep tokens regardless of model score ([#1400](#1400)) ([42612c8](42612c8)) * **langchain:** disable streaming on wrapped model during ainvoke() ([#1287](#1287)) ([3590046](3590046)) * **mcp:** register managed installs with a resolvable headroom command ([#1386](#1386)) ([22def93](22def93)) * **mcp:** report correct savings_percent in headroom_compress ([#1106](#1106)) ([f216e43](f216e43)) * **opencode:** write local MCP config ([#1381](#1381)) ([6c83790](6c83790)) * **packaging:** move hnswlib to optional [vector] extra so [all] needs no C++ toolchain ([#1499](#1499)) ([80fa086](80fa086)) * patch rtk hook script to use absolute path after register_claude_hooks ([#571](#571)) ([b618d2d](b618d2d)) * **perf:** surface RTK/CLI context-tool savings in perf and the session card ([#1433](#1433)) ([9362747](9362747)) * **proxy:** add --protect-tool-results to prevent lossy compression of exact-output Bash results ([#1374](#1374)) ([51d4bcf](51d4bcf)) * **proxy:** add an Anthropic buffered read-timeout override ([#1331](#1331)) ([3be2526](3be2526)) * **proxy:** add versionless Vertex AI routes for Claude Code compatibility ([#1321](#1321)) ([bb3e040](bb3e040)) * **proxy:** bind before eager preload so a hung compressor load can't block startup ([#1500](#1500)) ([d5ac07f](d5ac07f)) * **proxy:** build SSL contexts for custom CA bundles ([#1134](#1134)) ([561ba17](561ba17)) * **proxy:** forward request-id headers on the streaming path ([#1100](#1100)) ([#1258](#1258)) ([3d59df7](3d59df7)) * **proxy:** gate CCR retrieve/compress endpoints to loopback ([#1338](#1338)) ([acafb2d](acafb2d)) * **proxy:** honor force_kompress routing profile ([#996](#996)) ([b4682d6](b4682d6)) * **proxy:** keep large compression results on the critical path ([#296](#296)) ([#1352](#1352)) ([90734b6](90734b6)) * **proxy:** offload /v1/compress to the compression executor to stop blocking the loop ([#1501](#1501)) ([27e010e](27e010e)) * **proxy:** preserve Responses memory continuations with store=false ([#1103](#1103)) ([cdfeeac](cdfeeac)) * **proxy:** queue mid-turn user messages on non-Bedrock streaming path ([#1377](#1377)) ([b09f027](b09f027)) * **proxy:** register interceptor in explicit transforms list when HEADROOM_INTERCEPT_ENABLED ([#1376](#1376)) ([55c700c](55c700c)) * **proxy:** report real input tokens on streaming message_start ([#1132](#1132)) ([#1305](#1305)) ([70cc96a](70cc96a)) * **proxy:** retry upstream 429 with Retry-After on both forwarders ([#1329](#1329)) ([90bee89](90bee89)) * **proxy:** retry upstream 529 overloaded like 429 on both forwarders ([#1495](#1495)) ([547b15d](547b15d)) * **proxy:** stop re-compressing headroom_retrieve output and emitting unredeemable markers ([#1323](#1323)) ([43494ff](43494ff)) * **proxy:** strip Codex lite header from OpenAI WebSockets ([#1543](#1543)) ([5d3803a](5d3803a)) * **read-lifecycle:** persist STALE Read originals in the CCR store ([#1488](#1488)) ([9157173](9157173)) * recover persistent proxy feature checks and reject non-Copilot exchange URL ([#1465](#1465)) ([16c638b](16c638b)) * remove agents.md ([#1540](#1540)) ([a7d3360](a7d3360)) * respect COPILOT_PROVIDER_TYPE env var when provider_type is auto ([#549](#549)) ([24cf256](24cf256)) * restore token-mode compression on frozen prefixes ([#1489](#1489)) ([8e0dadf](8e0dadf)) * **router:** degrade to pure-Python detection on native panic ([#1123](#1123)) ([#1260](#1260)) ([a00fb67](a00fb67)) * **rtk:** stop hook registration timing out on a forked daemon ([#1314](#1314)) ([9758817](9758817)) * **smart-crusher:** honor enable_ccr_marker on the opaque-blob path ([#1130](#1130)) ([27d6f8e](27d6f8e)) * **subscription:** only reset 5h contribution on real rollover, not API jitter ([#1255](#1255)) ([8d6c175](8d6c175)) * **subscription:** run transcript token scan off the event loop ([#1263](#1263)) ([f03021f](f03021f)) * surface output reduction without a restart, and explain $0.00 savings on Python 3.14 ([#1296](#1296)) ([c30ec4c](c30ec4c)) * **tests:** reset whole headroom logger subtree so caplog stays deterministic ([#1117](#1117)) ([fda4670](fda4670)) * **tls:** add HEADROOM_TLS_STRICT=0 toggle for corporate SSL inspection ([#1308](#1308)) ([#1341](#1341)) ([52068dd](52068dd)) * **tokenizers:** price CJK/Kana/Hangul at ~1 token per char in EstimatingTokenCounter ([#1093](#1093)) ([a35fe86](a35fe86)) * **transforms:** gate tool string output from lossy compression ([#1307](#1307)) ([#1387](#1387)) ([c6c921a](c6c921a)) * **websocket:** harden responses websocket origin handling ([#1481](#1481)) ([c632023](c632023)) * **windows:** pin UTF-8 encoding on text-mode subprocess calls ([#1311](#1311)) ([d633e81](d633e81)) * **wrap:** add Copilot unwrap command ([#1251](#1251)) ([b4fde0c](b4fde0c)) * **wrap:** isolate proxy stdio from proxy.log on Windows ([#1191](#1191)) ([959ab0d](959ab0d)) * **wrap:** keep agent savings opt-in ([#1294](#1294)) ([b829ceb](b829ceb)) * **wrap:** show the dashboard URL when the proxy is already running ([#1313](#1313)) ([b0146c4](b0146c4)) ### Performance Improvements * **compression:** take large cold-start contexts off the synchronous kompress path ([#1171](#1171)) ([#1298](#1298)) ([6c68ff4](6c68ff4)) </details> --- This PR was generated with [Release Please](https://github.com/googleapis/release-please). See [documentation](https://github.com/googleapis/release-please#release-please). Co-authored-by: github-actions[bot] <41898282+github-actions[bot]@users.noreply.github.com>
🤖 I have created a release *beep* *boop* --- <details><summary>0.28.0</summary> ## [0.28.0](headroomlabs-ai/headroom@v0.27.0...v0.28.0) (2026-06-29) ### Features * add --disable-kompress-fallback to restore legacy PASSTHROUGH fallback ([headroomlabs-ai#1185](headroomlabs-ai#1185)) ([f309244](headroomlabs-ai@f309244)) * add first-class OpenCode support (wrap, learn, mcp install) ([headroomlabs-ai#559](headroomlabs-ai#559)) ([91cd210](headroomlabs-ai@91cd210)) * add HEADROOM_KEEPALIVE_EXPIRY to keep upstream connections warm ([headroomlabs-ai#1124](headroomlabs-ai#1124)) ([85786b3](headroomlabs-ai@85786b3)) * **azure-foundry:** derive upstream URL from ANTHROPIC_FOUNDRY_RESOURCE ([headroomlabs-ai#1138](headroomlabs-ai#1138)) ([e5031b0](headroomlabs-ai@e5031b0)) * **cache:** attribute prompt-cache misses to TTL lapse vs prefix change ([headroomlabs-ai#1313](headroomlabs-ai#1313)) ([headroomlabs-ai#1343](headroomlabs-ai#1343)) ([4658721](headroomlabs-ai@4658721)) * **code:** add Perl support to code-aware compressor ([headroomlabs-ai#1125](headroomlabs-ai#1125)) ([f39858c](headroomlabs-ai@f39858c)) * headroom wrap opencode / unwrap opencode CLI ([headroomlabs-ai#1105](headroomlabs-ai#1105)) ([b4571cc](headroomlabs-ai@b4571cc)) * **learn:** weight loops in Headroom Learn + RTK-loop eval ([headroomlabs-ai#1160](headroomlabs-ai#1160)) ([14e8dc4](headroomlabs-ai@14e8dc4)) * **learn:** write per-project learnings to CLAUDE.local.md by default ([headroomlabs-ai#1115](headroomlabs-ai#1115)) ([ced75e4](headroomlabs-ai@ced75e4)) * **proxy:** add request timeout config ([headroomlabs-ai#738](headroomlabs-ai#738)) ([c0745d4](headroomlabs-ai@c0745d4)) * **proxy:** pilot hardening — inbound auth, security headers, audit log, air-gap switch ([headroomlabs-ai#1537](headroomlabs-ai#1537)) ([546ab55](headroomlabs-ai@546ab55)) * **proxy:** support glob patterns in exclude_tools ([headroomlabs-ai#870](headroomlabs-ai#870)) ([headroomlabs-ai#1259](headroomlabs-ai#1259)) ([a2159c0](headroomlabs-ai@a2159c0)) * **read-maturation:** activity-based hold-back Read maturation (Mechanism B) ([headroomlabs-ai#1068](headroomlabs-ai#1068)) ([723b80c](headroomlabs-ai@723b80c)) * **savings:** durable savings ledger + headroom savings command ([headroomlabs-ai#1127](headroomlabs-ai#1127)) ([978ffa0](headroomlabs-ai@978ffa0)) * **wrap:** add --1m to preserve the 1M context window on wrap claude ([headroomlabs-ai#1158](headroomlabs-ai#1158)) ([headroomlabs-ai#1351](headroomlabs-ai#1351)) ([b50d9c1](headroomlabs-ai@b50d9c1)) * **wrap:** make tokensave the primary coding-task compressor, Serena the backup ([headroomlabs-ai#1230](headroomlabs-ai#1230)) ([dca9853](headroomlabs-ai@dca9853)) ### Bug Fixes * **agent-evals:** Phase 0 — coding-agent accuracy A/B framework ([headroomlabs-ai#1037](headroomlabs-ai#1037)) ([84f9871](headroomlabs-ai@84f9871)) * **agno:** tolerate streaming tool-call SDK objects in parser ([headroomlabs-ai#1312](headroomlabs-ai#1312)) ([headroomlabs-ai#1336](headroomlabs-ai#1336)) ([5986c22](headroomlabs-ai@5986c22)) * **bedrock:** add boto3 1.41 + CRT for aws login credentials ([headroomlabs-ai#1486](headroomlabs-ai#1486)) ([4db3bc9](headroomlabs-ai@4db3bc9)) * bump codebase-memory-mcp to v0.8.1 ([headroomlabs-ai#1284](headroomlabs-ai#1284)) ([530318b](headroomlabs-ai@530318b)) * **ccr:** make headroom_retrieve a hash-only full-content lookup ([headroomlabs-ai#1532](headroomlabs-ai#1532)) ([c2fc4d3](headroomlabs-ai@c2fc4d3)) * **ccr:** propagate --no-ccr-marker flag to all compressors ([headroomlabs-ai#1022](headroomlabs-ai#1022)) ([headroomlabs-ai#1197](headroomlabs-ai#1197)) ([0c9b42a](headroomlabs-ai@0c9b42a)) * **ccr:** skip Anthropic marker emission when tool injection is deferred ([headroomlabs-ai#1273](headroomlabs-ai#1273)) ([2cae13d](headroomlabs-ai@2cae13d)) * **ci:** extend gitleaks allowlist to cover test fixtures + verified examples ([headroomlabs-ai#1539](headroomlabs-ai#1539)) ([d2565a6](headroomlabs-ai@d2565a6)) * **ci:** guarantee model present in test shards to end cache-miss flakiness ([headroomlabs-ai#1399](headroomlabs-ai#1399)) ([2e29c72](headroomlabs-ai@2e29c72)) * **ci:** normalize Windows CRLF line endings in PR governance script ([headroomlabs-ai#1012](headroomlabs-ai#1012)) ([5194388](headroomlabs-ai@5194388)) * **cli:** add explicit UTF-8 encoding to file I/O in wrap commands ([headroomlabs-ai#1126](headroomlabs-ai#1126)) ([headroomlabs-ai#1164](headroomlabs-ai#1164)) ([a0cb798](headroomlabs-ai@a0cb798)) * **cli:** fall back gracefully when embedding-server sidecar is absent ([headroomlabs-ai#1206](headroomlabs-ai#1206)) ([38f1404](headroomlabs-ai@38f1404)) * **cli:** harden all CLI surfaces + fix docs accuracy ([headroomlabs-ai#1491](headroomlabs-ai#1491)) ([bd76235](headroomlabs-ai@bd76235)) * **cli:** wire --http2/--no-http2 (HEADROOM_HTTP2) into proxy command ([headroomlabs-ai#1373](headroomlabs-ai#1373)) ([e06b616](headroomlabs-ai@e06b616)) * **cli:** wire --rpm/--tpm and HEADROOM_RPM/HEADROOM_TPM to the Click proxy command ([headroomlabs-ai#1375](headroomlabs-ai#1375)) ([8aab8f2](headroomlabs-ai@8aab8f2)) * **code:** slice tree-sitter byte offsets as UTF-8 ([headroomlabs-ai#1332](headroomlabs-ai#1332)) ([8238402](headroomlabs-ai@8238402)) * **code:** validate Python compressed syntax ([headroomlabs-ai#1302](headroomlabs-ai#1302)) ([cbd361d](headroomlabs-ai@cbd361d)) * **code:** verify a real parse in tree-sitter availability check ([headroomlabs-ai#1231](headroomlabs-ai#1231)) ([headroomlabs-ai#1299](headroomlabs-ai#1299)) ([5e0bb69](headroomlabs-ai@5e0bb69)) * **codex:** retag threads on init so Codex Desktop history stays visible ([headroomlabs-ai#961](headroomlabs-ai#961)) ([headroomlabs-ai#1349](headroomlabs-ai#1349)) ([e6bbc40](headroomlabs-ai@e6bbc40)) * **codex:** stop pinning Codex memory MCP to one project db ([headroomlabs-ai#1269](headroomlabs-ai#1269)) ([ad7993b](headroomlabs-ai@ad7993b)) * **dashboard:** include RTK stats in the historical tab ([headroomlabs-ai#1324](headroomlabs-ai#1324)) ([35939c3](headroomlabs-ai@35939c3)) * **deps:** remediate dependency CVEs and publish SBOM ([headroomlabs-ai#1509](headroomlabs-ai#1509)) ([5771a80](headroomlabs-ai@5771a80)) * **docker:** persist session history across container revisions ([headroomlabs-ai#1118](headroomlabs-ai#1118)) ([5912d65](headroomlabs-ai@5912d65)) * **gemini:** offload compression to the executor ([headroomlabs-ai#1382](headroomlabs-ai#1382)) ([615848e](headroomlabs-ai@615848e)) * **gemini:** resolve Google model capabilities through ModelRegistry ([headroomlabs-ai#1276](headroomlabs-ai#1276)) ([17ecad9](headroomlabs-ai@17ecad9)) * **install:** guard install_agent_ensure against duplicate runtime spawns ([headroomlabs-ai#1301](headroomlabs-ai#1301)) ([8da0b4e](headroomlabs-ai@8da0b4e)) * **install:** repair macOS launchd restart/start lifecycle ([headroomlabs-ai#1290](headroomlabs-ai#1290)) ([da1a397](headroomlabs-ai@da1a397)) * **install:** stop duplicating ENTRYPOINT in persistent-docker runtime command ([headroomlabs-ai#833](headroomlabs-ai#833)) ([headroomlabs-ai#1348](headroomlabs-ai#1348)) ([feedead](headroomlabs-ai@feedead)) * **io:** use UTF-8 with locale fallback and preserve line endings on config/text I/O ([headroomlabs-ai#1498](headroomlabs-ai#1498)) ([1baa04e](headroomlabs-ai@1baa04e)) * **kompress:** hard override keeps must-keep tokens regardless of model score ([headroomlabs-ai#1400](headroomlabs-ai#1400)) ([42612c8](headroomlabs-ai@42612c8)) * **langchain:** disable streaming on wrapped model during ainvoke() ([headroomlabs-ai#1287](headroomlabs-ai#1287)) ([3590046](headroomlabs-ai@3590046)) * **mcp:** register managed installs with a resolvable headroom command ([headroomlabs-ai#1386](headroomlabs-ai#1386)) ([22def93](headroomlabs-ai@22def93)) * **mcp:** report correct savings_percent in headroom_compress ([headroomlabs-ai#1106](headroomlabs-ai#1106)) ([f216e43](headroomlabs-ai@f216e43)) * **opencode:** write local MCP config ([headroomlabs-ai#1381](headroomlabs-ai#1381)) ([6c83790](headroomlabs-ai@6c83790)) * **packaging:** move hnswlib to optional [vector] extra so [all] needs no C++ toolchain ([headroomlabs-ai#1499](headroomlabs-ai#1499)) ([80fa086](headroomlabs-ai@80fa086)) * patch rtk hook script to use absolute path after register_claude_hooks ([headroomlabs-ai#571](headroomlabs-ai#571)) ([b618d2d](headroomlabs-ai@b618d2d)) * **perf:** surface RTK/CLI context-tool savings in perf and the session card ([headroomlabs-ai#1433](headroomlabs-ai#1433)) ([9362747](headroomlabs-ai@9362747)) * **proxy:** add --protect-tool-results to prevent lossy compression of exact-output Bash results ([headroomlabs-ai#1374](headroomlabs-ai#1374)) ([51d4bcf](headroomlabs-ai@51d4bcf)) * **proxy:** add an Anthropic buffered read-timeout override ([headroomlabs-ai#1331](headroomlabs-ai#1331)) ([3be2526](headroomlabs-ai@3be2526)) * **proxy:** add versionless Vertex AI routes for Claude Code compatibility ([headroomlabs-ai#1321](headroomlabs-ai#1321)) ([bb3e040](headroomlabs-ai@bb3e040)) * **proxy:** bind before eager preload so a hung compressor load can't block startup ([headroomlabs-ai#1500](headroomlabs-ai#1500)) ([d5ac07f](headroomlabs-ai@d5ac07f)) * **proxy:** build SSL contexts for custom CA bundles ([headroomlabs-ai#1134](headroomlabs-ai#1134)) ([561ba17](headroomlabs-ai@561ba17)) * **proxy:** forward request-id headers on the streaming path ([headroomlabs-ai#1100](headroomlabs-ai#1100)) ([headroomlabs-ai#1258](headroomlabs-ai#1258)) ([3d59df7](headroomlabs-ai@3d59df7)) * **proxy:** gate CCR retrieve/compress endpoints to loopback ([headroomlabs-ai#1338](headroomlabs-ai#1338)) ([acafb2d](headroomlabs-ai@acafb2d)) * **proxy:** honor force_kompress routing profile ([headroomlabs-ai#996](headroomlabs-ai#996)) ([b4682d6](headroomlabs-ai@b4682d6)) * **proxy:** keep large compression results on the critical path ([headroomlabs-ai#296](headroomlabs-ai#296)) ([headroomlabs-ai#1352](headroomlabs-ai#1352)) ([90734b6](headroomlabs-ai@90734b6)) * **proxy:** offload /v1/compress to the compression executor to stop blocking the loop ([headroomlabs-ai#1501](headroomlabs-ai#1501)) ([27e010e](headroomlabs-ai@27e010e)) * **proxy:** preserve Responses memory continuations with store=false ([headroomlabs-ai#1103](headroomlabs-ai#1103)) ([cdfeeac](headroomlabs-ai@cdfeeac)) * **proxy:** queue mid-turn user messages on non-Bedrock streaming path ([headroomlabs-ai#1377](headroomlabs-ai#1377)) ([b09f027](headroomlabs-ai@b09f027)) * **proxy:** register interceptor in explicit transforms list when HEADROOM_INTERCEPT_ENABLED ([headroomlabs-ai#1376](headroomlabs-ai#1376)) ([55c700c](headroomlabs-ai@55c700c)) * **proxy:** report real input tokens on streaming message_start ([headroomlabs-ai#1132](headroomlabs-ai#1132)) ([headroomlabs-ai#1305](headroomlabs-ai#1305)) ([70cc96a](headroomlabs-ai@70cc96a)) * **proxy:** retry upstream 429 with Retry-After on both forwarders ([headroomlabs-ai#1329](headroomlabs-ai#1329)) ([90bee89](headroomlabs-ai@90bee89)) * **proxy:** retry upstream 529 overloaded like 429 on both forwarders ([headroomlabs-ai#1495](headroomlabs-ai#1495)) ([547b15d](headroomlabs-ai@547b15d)) * **proxy:** stop re-compressing headroom_retrieve output and emitting unredeemable markers ([headroomlabs-ai#1323](headroomlabs-ai#1323)) ([43494ff](headroomlabs-ai@43494ff)) * **proxy:** strip Codex lite header from OpenAI WebSockets ([headroomlabs-ai#1543](headroomlabs-ai#1543)) ([5d3803a](headroomlabs-ai@5d3803a)) * **read-lifecycle:** persist STALE Read originals in the CCR store ([headroomlabs-ai#1488](headroomlabs-ai#1488)) ([9157173](headroomlabs-ai@9157173)) * recover persistent proxy feature checks and reject non-Copilot exchange URL ([headroomlabs-ai#1465](headroomlabs-ai#1465)) ([16c638b](headroomlabs-ai@16c638b)) * remove agents.md ([headroomlabs-ai#1540](headroomlabs-ai#1540)) ([a7d3360](headroomlabs-ai@a7d3360)) * respect COPILOT_PROVIDER_TYPE env var when provider_type is auto ([headroomlabs-ai#549](headroomlabs-ai#549)) ([24cf256](headroomlabs-ai@24cf256)) * restore token-mode compression on frozen prefixes ([headroomlabs-ai#1489](headroomlabs-ai#1489)) ([8e0dadf](headroomlabs-ai@8e0dadf)) * **router:** degrade to pure-Python detection on native panic ([headroomlabs-ai#1123](headroomlabs-ai#1123)) ([headroomlabs-ai#1260](headroomlabs-ai#1260)) ([a00fb67](headroomlabs-ai@a00fb67)) * **rtk:** stop hook registration timing out on a forked daemon ([headroomlabs-ai#1314](headroomlabs-ai#1314)) ([9758817](headroomlabs-ai@9758817)) * **smart-crusher:** honor enable_ccr_marker on the opaque-blob path ([headroomlabs-ai#1130](headroomlabs-ai#1130)) ([27d6f8e](headroomlabs-ai@27d6f8e)) * **subscription:** only reset 5h contribution on real rollover, not API jitter ([headroomlabs-ai#1255](headroomlabs-ai#1255)) ([8d6c175](headroomlabs-ai@8d6c175)) * **subscription:** run transcript token scan off the event loop ([headroomlabs-ai#1263](headroomlabs-ai#1263)) ([f03021f](headroomlabs-ai@f03021f)) * surface output reduction without a restart, and explain $0.00 savings on Python 3.14 ([headroomlabs-ai#1296](headroomlabs-ai#1296)) ([c30ec4c](headroomlabs-ai@c30ec4c)) * **tests:** reset whole headroom logger subtree so caplog stays deterministic ([headroomlabs-ai#1117](headroomlabs-ai#1117)) ([fda4670](headroomlabs-ai@fda4670)) * **tls:** add HEADROOM_TLS_STRICT=0 toggle for corporate SSL inspection ([headroomlabs-ai#1308](headroomlabs-ai#1308)) ([headroomlabs-ai#1341](headroomlabs-ai#1341)) ([52068dd](headroomlabs-ai@52068dd)) * **tokenizers:** price CJK/Kana/Hangul at ~1 token per char in EstimatingTokenCounter ([headroomlabs-ai#1093](headroomlabs-ai#1093)) ([a35fe86](headroomlabs-ai@a35fe86)) * **transforms:** gate tool string output from lossy compression ([headroomlabs-ai#1307](headroomlabs-ai#1307)) ([headroomlabs-ai#1387](headroomlabs-ai#1387)) ([c6c921a](headroomlabs-ai@c6c921a)) * **websocket:** harden responses websocket origin handling ([headroomlabs-ai#1481](headroomlabs-ai#1481)) ([c632023](headroomlabs-ai@c632023)) * **windows:** pin UTF-8 encoding on text-mode subprocess calls ([headroomlabs-ai#1311](headroomlabs-ai#1311)) ([d633e81](headroomlabs-ai@d633e81)) * **wrap:** add Copilot unwrap command ([headroomlabs-ai#1251](headroomlabs-ai#1251)) ([b4fde0c](headroomlabs-ai@b4fde0c)) * **wrap:** isolate proxy stdio from proxy.log on Windows ([headroomlabs-ai#1191](headroomlabs-ai#1191)) ([959ab0d](headroomlabs-ai@959ab0d)) * **wrap:** keep agent savings opt-in ([headroomlabs-ai#1294](headroomlabs-ai#1294)) ([b829ceb](headroomlabs-ai@b829ceb)) * **wrap:** show the dashboard URL when the proxy is already running ([headroomlabs-ai#1313](headroomlabs-ai#1313)) ([b0146c4](headroomlabs-ai@b0146c4)) ### Performance Improvements * **compression:** take large cold-start contexts off the synchronous kompress path ([headroomlabs-ai#1171](headroomlabs-ai#1171)) ([headroomlabs-ai#1298](headroomlabs-ai#1298)) ([6c68ff4](headroomlabs-ai@6c68ff4)) </details> --- This PR was generated with [Release Please](https://github.com/googleapis/release-please). See [documentation](https://github.com/googleapis/release-please#release-please). Co-authored-by: github-actions[bot] <41898282+github-actions[bot]@users.noreply.github.com>
Description
Build explicit
ssl.SSLContextobjects for custom CA bundles configured throughSSL_CERT_FILEandREQUESTS_CA_BUNDLE. Python 3.13 / newer OpenSSL can reject some enterprise/private PKI roots that platform TLS stacks accept, for example roots without akeyUsageextension. The new custom-CA contexts keep certificate verification enabled while clearing onlyssl.VERIFY_X509_STRICT.Closes #
Type of Change
Changes Made
SSLContextobjects forSSL_CERT_FILEandREQUESTS_CA_BUNDLEinstead of passing raw CA bundle paths to httpx.ssl.VERIFY_X509_STRICTfor operator-provided custom CA contexts; certificate verification, hostname verification, expiry checks, and chain validation stay enabled.NODE_EXTRA_CA_CERTSadditive behavior by loading the extra CA bundle on top of the default/system trust store.Testing
pytest)ruff check .)mypy headroom)Test Output
Real Behavior Proof
SSL_CERT_FILE/REQUESTS_CA_BUNDLE/NODE_EXTRA_CA_CERTSpointed at an enterprise/private PKI CA bundle. Upstream HTTPS endpoint name is redacted.headroom.proxy.ssl_context.find_ca_bundle(), passes the returned verifier intohttpx.AsyncClient(verify=...), and performs a GET against the enterprise HTTPS endpoint that previously failed with OpenSSL strict verification.SSLContext, strict X.509 verification was disabled for that custom CA context, and the request reached the upstream HTTP response:uv run pytest,uv sync --extra dev, andmypy headroomin this local environment. The editable build currently fails before tests run because Cargo'sort-sysbuild script cannot download ORT prebuilt binaries due an unrelated local certificate verification error against the ORT CDN. No dependency or lockfile changes are included in this PR.Review Readiness
Checklist
Screenshots (if applicable)
N/A.
Additional Notes
No dependencies or lockfiles changed. Documentation is unchanged because this is a bug fix to existing custom CA environment-variable behavior rather than a new user-facing configuration surface.