From ca22f46ca3341a3b115c4326f69246e17b364899 Mon Sep 17 00:00:00 2001
From: danielmeppiel <danielmeppiel@users.noreply.github.com>
Date: Sat, 17 Oct 2026 04:55:38 +0200
Subject: [PATCH] fix(runtime): keep APM truststore bootstrap out of ensurepip
 on llm re-setup

Re-running `apm runtime setup llm` over an existing venv recreates it while
APM's `_apm_tls.pth` bootstrap is installed. ensurepip launches its bundled
pip via `python -c runpy...`, which the bootstrap's pip detection misses, so
truststore is injected into ssl; pip's vendored truststore then probes
`create_default_context().wrap_bio(...)` and truststore 0.10.5 rejects it
("check_hostname requires server_hostname"). Run the pip bootstrap with
APM_DISABLE_TRUSTSTORE=1 (honored by every shipped bootstrap); pip still
verifies against the OS store through its own vendored truststore.

Co-authored-by: Copilot App <223556219+Copilot@users.noreply.github.com>
Copilot-Session: 761bf207-57da-41d0-bd3f-ffecbb97b83a
---
 scripts/runtime/setup-llm.ps1           | 11 +++++++++--
 scripts/runtime/setup-llm.sh            |  6 ++++--
 tests/integration/test_tls_r3_verify.py | 10 ++++++++++
 3 files changed, 23 insertions(+), 4 deletions(-)

diff --git a/scripts/runtime/setup-llm.ps1 b/scripts/runtime/setup-llm.ps1
index 0cd2a78dd3..1c18a93379 100644
--- a/scripts/runtime/setup-llm.ps1
+++ b/scripts/runtime/setup-llm.ps1
@@ -26,9 +26,16 @@ function Install-Llm {
         exit 1
     }
 
-    # Create virtual environment
+    # Create virtual environment. A re-run over an existing venv must not let
+    # APM's truststore .pth bootstrap inject into ensurepip's bundled pip.
     Write-Info "Creating Python virtual environment for LLM..."
-    python -m venv $llmVenv
+    $previousDisable = $env:APM_DISABLE_TRUSTSTORE
+    $env:APM_DISABLE_TRUSTSTORE = "1"
+    try {
+        python -m venv $llmVenv
+    } finally {
+        $env:APM_DISABLE_TRUSTSTORE = $previousDisable
+    }
 
     $pipExe = Join-Path (Join-Path $llmVenv "Scripts") "pip.exe"
     $llmExe = Join-Path (Join-Path $llmVenv "Scripts") "llm.exe"
diff --git a/scripts/runtime/setup-llm.sh b/scripts/runtime/setup-llm.sh
index 60d8649ff0..4d20fec32c 100755
--- a/scripts/runtime/setup-llm.sh
+++ b/scripts/runtime/setup-llm.sh
@@ -43,7 +43,9 @@ setup_llm() {
     
     # Create virtual environment for LLM. Bootstrap pip as a separate step:
     # `python3 -m venv` hides ensurepip's output, so a failure would only
-    # report "exit status 1" without the reason.
+    # report "exit status 1" without the reason. A re-run over an existing venv
+    # must not let APM's truststore .pth bootstrap inject into ensurepip's
+    # bundled pip, whose vendored truststore rejects an already-injected ssl.
     local python3_bin
     python3_bin="$(command -v python3)"
     log_info "Creating Python virtual environment for LLM (using $python3_bin)..."
@@ -51,7 +53,7 @@ setup_llm() {
         log_error "Could not create the LLM virtual environment at $llm_venv."
         exit 1
     fi
-    if ! "$llm_venv/bin/python" -m ensurepip --upgrade --default-pip; then
+    if ! APM_DISABLE_TRUSTSTORE=1 "$llm_venv/bin/python" -m ensurepip --upgrade --default-pip; then
         log_error "Could not bootstrap pip into $llm_venv (python3: $python3_bin)."
         exit 1
     fi
diff --git a/tests/integration/test_tls_r3_verify.py b/tests/integration/test_tls_r3_verify.py
index 57eed8e7d9..3a76bd3300 100644
--- a/tests/integration/test_tls_r3_verify.py
+++ b/tests/integration/test_tls_r3_verify.py
@@ -309,6 +309,16 @@ def spy(target, data):
     )
 
 
+def test_setup_llm_pip_bootstrap_skips_apm_truststore_injection():
+    """Re-running setup over a bootstrapped venv must not inject into ensurepip's pip."""
+    root = _repo_root()
+    sh = (root / "scripts" / "runtime" / "setup-llm.sh").read_text(encoding="utf-8")
+    ps1 = (root / "scripts" / "runtime" / "setup-llm.ps1").read_text(encoding="utf-8")
+
+    assert 'APM_DISABLE_TRUSTSTORE=1 "$llm_venv/bin/python" -m ensurepip' in sh
+    assert '$env:APM_DISABLE_TRUSTSTORE = "1"' in ps1
+
+
 # --------------------------------------------------------------------------- #
 # V4 (M1): runtime setup scripts install truststore best-effort + pinned
 # --------------------------------------------------------------------------- #