diff --git a/pyproject.toml b/pyproject.toml
index 442ee1670..5324b86d9 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -48,7 +48,13 @@ dependencies = [
     "sqlalchemy>=2.0.0",
     "psycopg[binary]>=3.2,<4",
     "aiosqlite>=0.19.0",
-    "python-jose[cryptography]>=3.3.0",
+    # NOTE: python-jose was removed here. It was never imported by this
+    # codebase -- the only "from jose import ..." occurrence is inside a string
+    # template in backend/code_generator.py, which writes its own
+    # requirements.txt for the project it generates. Declaring it dragged in
+    # ecdsa, whose GHSA-wj6h-64fc-37mp has no patched release. passlib below is
+    # the same template-only case but carries no advisory; it can be dropped
+    # too if generated-project deps are confirmed self-contained.
     "passlib[bcrypt]>=1.7.4",
     "python-decouple>=3.8",
     "structlog>=23.2.0",
@@ -91,6 +97,10 @@ dev = [
     "ipykernel>=6.25.0",
     "notebook>=7.0.0",
     "locust==2.46.0",
+    # Test-time only. TestGeneratedFastAPIBehaviour executes the FastAPI app
+    # that code_generator emits, and that app imports jwt. EventRelay itself
+    # never imports it, so it does not belong in the runtime dependencies.
+    "pyjwt>=2.10.1",
 ]
 docs = [
     "mkdocs>=1.5.0",
diff --git a/requirements.txt b/requirements.txt
index ddb75dacc..1e7d37739 100644
--- a/requirements.txt
+++ b/requirements.txt
@@ -29,7 +29,9 @@ aiosqlite>=0.19.0
 alembic>=1.12.0
 
 # Security & Auth
-python-jose[cryptography]>=3.3.0
+# python-jose removed: never imported here (only inside a code_generator.py
+# string template, which emits its own requirements.txt). It pulled in ecdsa,
+# whose GHSA-wj6h-64fc-37mp has no patched release.
 passlib[bcrypt]>=1.7.4
 
 # Configuration
diff --git a/shared/libs/youtube_proxy.py b/shared/libs/youtube_proxy.py
index 77c354095..1020a8434 100644
--- a/shared/libs/youtube_proxy.py
+++ b/shared/libs/youtube_proxy.py
@@ -12,6 +12,7 @@
 import logging
 import os
 import random
+import re
 import time
 import urllib.parse
 from dataclasses import dataclass
@@ -72,20 +73,71 @@ def _get_transcript_proxy_config() -> GenericProxyConfig | None:
     return GenericProxyConfig(http_url=url, https_url=url)
 
 
-def _redact_proxy_credentials(text: str) -> str:
-    """Strip user:pass credentials of the configured proxy URL from text."""
-    url = os.getenv("WEBSHARE_PROXY_URL", "").strip()
-    if not url or url not in text:
-        return text
+# Matches the ``user[:password]@`` userinfo segment of any URL. Kept byte-identical
+# to the canonical copy in ``src/youtube_extension/utils/proxy.py``; see that module
+# for the full rationale. In short: the classes exclude the authority delimiters
+# (whitespace, "/", "?", "#") so paths and query strings containing "@" are never
+# mistaken for credentials, but they permit a literal "@" so an unencoded one in
+# the password is consumed whole rather than leaving the tail behind.
+_USERINFO_RE = re.compile(
+    r"(?P<scheme>[A-Za-z][A-Za-z0-9+.\-]*://)"
+    r"(?P<user>[^\s/:?#]*)"
+    r"(?::(?P<password>[^\s/?#]*))?"
+    r"@"
+)
+
+_REDACTED = "***"
+_UNPRINTABLE = "<unprintable error>"
+_REDACTION_FAILED = "<redaction failed>"
+
+
+def _redact_proxy_credentials(text: Any) -> str:
+    """Strip URL userinfo (``user:pass@``) from ``text``.
+
+    Two passes: exact replacement of the configured ``WEBSHARE_PROXY_URL`` (which
+    preserves the host, so operators can still tell which proxy was in play),
+    then a generic ``scheme://user:pass@`` sweep that catches credentials never
+    matching the env value verbatim -- a normalised or percent-encoded form
+    echoed back by yt-dlp, a ``CalledProcessError`` repr of the argv, or a
+    different proxy variable such as ``HTTPS_PROXY``.
+
+    Never raises: every caller here is an exception handler, where a failure
+    would mask the original error.
+    """
+    if isinstance(text, str):
+        candidate = text
+    else:
+        try:
+            candidate = str(text)
+        except Exception:  # noqa: BLE001 - a hostile __str__ must not propagate
+            return _UNPRINTABLE
+
     try:
-        parsed = urllib.parse.urlparse(url)
-        netloc = parsed.hostname or ""
-        if parsed.port:
-            netloc = f"{netloc}:{parsed.port}"
-        redacted = parsed._replace(netloc=netloc).geturl()
-    except (ValueError, AttributeError):
-        redacted = "<proxy-url>"
-    return text.replace(url, redacted)
+        return _redact(candidate)
+    except Exception:  # noqa: BLE001 - never return text we cannot vouch for
+        return _REDACTION_FAILED
+
+
+def _redact(text: str) -> str:
+    """Run the two redaction passes over an already-stringified ``text``."""
+    url = os.getenv("WEBSHARE_PROXY_URL", "").strip()
+    if url and url in text:
+        try:
+            parsed = urllib.parse.urlparse(url)
+            netloc = parsed.hostname or ""
+            if parsed.port:
+                netloc = f"{netloc}:{parsed.port}"
+            redacted = parsed._replace(netloc=netloc).geturl()
+        except (ValueError, AttributeError):
+            redacted = "<proxy-url>"
+        text = text.replace(url, redacted)
+
+    def _mask(match: re.Match[str]) -> str:
+        if match.group("password") is None:
+            return f"{match.group('scheme')}{_REDACTED}@"
+        return f"{match.group('scheme')}{_REDACTED}:{_REDACTED}@"
+
+    return _USERINFO_RE.sub(_mask, text)
 
 class YouTubeErrorType(Enum):
     """YouTube API specific error types"""
diff --git a/src/youtube_extension/backend/code_generator.py b/src/youtube_extension/backend/code_generator.py
index 614fe8490..5de39057c 100644
--- a/src/youtube_extension/backend/code_generator.py
+++ b/src/youtube_extension/backend/code_generator.py
@@ -463,9 +463,14 @@ async def _generate_python_api(self, project_path: Path, video_analysis: dict, f
         if "database" in features:
             requirements.append("sqlalchemy==2.0.23")
         if "authentication" in features:
-            # The generated main.py imports passlib.context; omitting it here
-            # produced a project that fails at import time.
-            requirements.append("python-jose[cryptography]==3.3.0")
+            # The generated main.py imports jwt and passlib.context; omitting
+            # either here produced a project that fails at import time.
+            #
+            # PyJWT rather than python-jose: python-jose depends on ecdsa,
+            # whose GHSA-wj6h-64fc-37mp has no patched release, so every
+            # generated project inherited an unfixable advisory. PyJWT is
+            # maintained and its encode/decode signatures are the same.
+            requirements.append("pyjwt>=2.10.1")
             requirements.append("passlib[bcrypt]==1.7.4")
 
         # Generate main.py
@@ -1115,7 +1120,8 @@ def _generate_fastapi_main(self, title: str, features: list[str]) -> str:
         if "authentication" in features:
             scaffolding_endpoints.append("POST /auth/login")
             auth_imports = '''
-from jose import JWTError, jwt
+import jwt
+from jwt import PyJWTError
 from passlib.context import CryptContext'''
             auth_code = '''
 # ─── Authentication ─────────────────────────────────────────────────────────
@@ -1162,7 +1168,7 @@ def decode_access_token(token: str) -> dict:
     key = _require_secret_key()
     try:
         return jwt.decode(token, key, algorithms=[ALGORITHM])
-    except JWTError as exc:
+    except PyJWTError as exc:
         raise HTTPException(status_code=401, detail="Invalid or expired token") from exc
 
 
diff --git a/src/youtube_extension/utils/proxy.py b/src/youtube_extension/utils/proxy.py
index def0da69e..f82a9481f 100644
--- a/src/youtube_extension/utils/proxy.py
+++ b/src/youtube_extension/utils/proxy.py
@@ -13,6 +13,7 @@
 
 import logging
 import os
+import re
 import urllib.parse
 from typing import Any
 
@@ -28,6 +29,38 @@
 
 _PROXY_ENV_VAR = "WEBSHARE_PROXY_URL"
 
+# Matches the ``user[:password]@`` userinfo segment of any URL.
+#
+# The classes exclude whitespace, "/", "?" and "#" -- the delimiters that end a
+# URL authority -- so a path, query, or fragment containing "@" (e.g.
+# "https://example.com/a@b" or "https://example.com?e=a@b") is never mistaken
+# for credentials, and a match can never span from one URL into the next.
+#
+# They deliberately *permit* a literal "@". RFC 3986 requires "@" inside
+# userinfo to be percent-encoded, but real *_PROXY values routinely carry a raw
+# one. Because the classes are greedy, the engine backtracks to the LAST "@"
+# inside the authority, so an unencoded "@" in the password
+# ("http://user:pa@ss@host") is consumed whole instead of the match stopping at
+# the first separator and leaving the password tail behind.
+#
+# The user may be empty so credentials with no username ("http://:pass@host")
+# are still redacted.
+_USERINFO_RE = re.compile(
+    r"(?P<scheme>[A-Za-z][A-Za-z0-9+.\-]*://)"
+    r"(?P<user>[^\s/:?#]*)"
+    r"(?::(?P<password>[^\s/?#]*))?"
+    r"@"
+)
+
+_REDACTED = "***"
+
+# Returned when the input cannot be stringified, or when redaction itself
+# fails. Both are fail-closed: emitting a fixed placeholder is preferable to
+# raising (which would mask the original error) or to returning text we cannot
+# guarantee is clean (which could leak the credential we are trying to strip).
+_UNPRINTABLE = "<unprintable error>"
+_REDACTION_FAILED = "<redaction failed>"
+
 
 def get_proxy_url() -> str | None:
     """Return the validated Webshare proxy URL, or None for direct connection."""
@@ -67,17 +100,59 @@ def get_transcript_proxy_config() -> Any | None:
     return GenericProxyConfig(http_url=url, https_url=url)
 
 
-def redact_proxy_credentials(text: str) -> str:
-    """Strip user:pass credentials of the configured proxy URL from text."""
-    url = os.getenv(_PROXY_ENV_VAR, "").strip()
-    if not url or url not in text:
-        return text
+def redact_proxy_credentials(text: Any) -> str:
+    """Strip URL userinfo (``user:pass@``) from ``text``.
+
+    Two passes, because either alone is insufficient:
+
+    1. Exact replacement of the configured ``WEBSHARE_PROXY_URL`` -- preserves
+       the host so operators can still tell *which* proxy was in play.
+    2. A generic ``scheme://user:pass@`` sweep -- catches credentials that never
+       match the env value verbatim: yt-dlp echoing a normalised or
+       percent-encoded form back on stderr, a ``CalledProcessError`` repr of the
+       argv, or a different proxy variable (``HTTPS_PROXY`` and friends)
+       entirely.
+
+    Pass 1 alone was the previous behaviour and leaked in all of those cases,
+    because it bailed out whenever the configured URL did not appear in the text
+    byte-for-byte.
+
+    Always returns a string and never raises; it is called from exception
+    handlers, where a failure would mask the original error. If ``text`` cannot
+    be stringified (a ``__str__`` that itself raises) or redaction fails, a
+    fixed non-sensitive placeholder is returned instead.
+    """
+    if isinstance(text, str):
+        candidate = text
+    else:
+        try:
+            candidate = str(text)
+        except Exception:  # noqa: BLE001 - a hostile __str__ must not propagate
+            return _UNPRINTABLE
+
     try:
-        parsed = urllib.parse.urlparse(url)
-        netloc = parsed.hostname or ""
-        if parsed.port:
-            netloc = f"{netloc}:{parsed.port}"
-        redacted = parsed._replace(netloc=netloc).geturl()
-    except (ValueError, AttributeError):
-        redacted = "<proxy-url>"
-    return text.replace(url, redacted)
+        return _redact(candidate)
+    except Exception:  # noqa: BLE001 - never return text we cannot vouch for
+        return _REDACTION_FAILED
+
+
+def _redact(text: str) -> str:
+    """Run the two redaction passes over an already-stringified ``text``."""
+    url = os.getenv(_PROXY_ENV_VAR, "").strip()
+    if url and url in text:
+        try:
+            parsed = urllib.parse.urlparse(url)
+            netloc = parsed.hostname or ""
+            if parsed.port:
+                netloc = f"{netloc}:{parsed.port}"
+            redacted = parsed._replace(netloc=netloc).geturl()
+        except (ValueError, AttributeError):
+            redacted = "<proxy-url>"
+        text = text.replace(url, redacted)
+
+    def _mask(match: re.Match[str]) -> str:
+        if match.group("password") is None:
+            return f"{match.group('scheme')}{_REDACTED}@"
+        return f"{match.group('scheme')}{_REDACTED}:{_REDACTED}@"
+
+    return _USERINFO_RE.sub(_mask, text)
diff --git a/tests/unit/test_code_generator.py b/tests/unit/test_code_generator.py
index aaf4456ab..fc9c09c11 100644
--- a/tests/unit/test_code_generator.py
+++ b/tests/unit/test_code_generator.py
@@ -1382,4 +1382,8 @@ def test_auth_projects_declare_their_password_hashing_dependency(
 
         requirements = (project_dir / "requirements.txt").read_text()
         assert "passlib" in requirements
-        assert "python-jose" in requirements
+        # PyJWT, not python-jose: the latter depends on ecdsa, whose
+        # GHSA-wj6h-64fc-37mp has no patched release, so every generated
+        # project inherited an unfixable advisory.
+        assert "pyjwt" in requirements
+        assert "python-jose" not in requirements
diff --git a/tests/unit/test_proxy_utils.py b/tests/unit/test_proxy_utils.py
new file mode 100644
index 000000000..8e24962ad
--- /dev/null
+++ b/tests/unit/test_proxy_utils.py
@@ -0,0 +1,175 @@
+"""Regression tests for proxy credential redaction.
+
+``redact_proxy_credentials`` is called from exception handlers that log
+subprocess and HTTP failures, so anything it fails to strip is written to logs
+verbatim. Every ``LEAKED`` case below reproduces text that leaked before the
+two-pass implementation landed.
+
+The helper exists in two copies -- the canonical
+``src/youtube_extension/utils/proxy.py`` and the standalone
+``shared/libs/youtube_proxy.py`` used by the importlib fallback path. Both are
+exercised here, because a fix applied to only one of them leaves the other
+leaking.
+"""
+
+from __future__ import annotations
+
+import importlib.util
+import pathlib
+import sys
+
+import pytest
+
+from youtube_extension.utils.proxy import redact_proxy_credentials
+
+_PROXY_ENV_VAR = "WEBSHARE_PROXY_URL"
+_CONFIGURED = "http://user:s3cr3t@proxy.internal:8080"
+
+
+def _load_shared_copy():
+    """Import ``shared/libs/youtube_proxy.py`` directly, without a package."""
+    path = (
+        pathlib.Path(__file__).resolve().parents[2]
+        / "shared"
+        / "libs"
+        / "youtube_proxy.py"
+    )
+    name = "_shared_youtube_proxy"
+    if name in sys.modules:
+        return sys.modules[name]
+    spec = importlib.util.spec_from_file_location(name, path)
+    assert spec and spec.loader
+    module = importlib.util.module_from_spec(spec)
+    # Register before exec: the module uses ``from __future__ import
+    # annotations``, so its dataclass field annotations are strings that
+    # ``dataclasses`` resolves by looking the module up in ``sys.modules``.
+    sys.modules[name] = module
+    try:
+        spec.loader.exec_module(module)
+    except Exception:
+        del sys.modules[name]
+        raise
+    return module
+
+
+@pytest.fixture(params=["canonical", "shared"])
+def redact(request):
+    """Both implementations, so neither can drift into leaking alone."""
+    if request.param == "canonical":
+        return redact_proxy_credentials
+    return _load_shared_copy()._redact_proxy_credentials
+
+
+@pytest.fixture(autouse=True)
+def _configured_proxy(monkeypatch):
+    monkeypatch.setenv(_PROXY_ENV_VAR, _CONFIGURED)
+
+
+# Each case is (text, secret-that-must-not-survive).
+LEAKED = [
+    pytest.param(
+        f"transcript fetch failed via {_CONFIGURED}",
+        "s3cr3t",
+        id="exact-configured-url",
+    ),
+    pytest.param(
+        f"ProxyError: {_CONFIGURED}/",
+        "s3cr3t",
+        id="trailing-slash-from-urllib3",
+    ),
+    # requests/urllib3 lowercase the host when re-rendering a URL, so the text
+    # no longer matches the env value byte-for-byte.
+    pytest.param(
+        "connect to http://user:s3cr3t@PROXY.INTERNAL:8080 refused",
+        "s3cr3t",
+        id="host-case-normalised",
+    ),
+    pytest.param(
+        "http://user:s3cr3t%40x@proxy.internal:8080",
+        "s3cr3t",
+        id="percent-encoded-password",
+    ),
+    # A different proxy variable entirely -- never equal to WEBSHARE_PROXY_URL,
+    # so the exact-match pass alone never touched it.
+    pytest.param(
+        "HTTPS_PROXY=http://bob:hunter2@corp.proxy:3128 connection refused",
+        "hunter2",
+        id="different-proxy-variable",
+    ),
+    # RFC 3986 requires "@" in userinfo to be percent-encoded, but real proxy
+    # values carry a raw one. Matching to the FIRST "@" left the tail behind.
+    pytest.param(
+        "http://user:pa@ss@proxy.internal:8080",
+        "ss@proxy",
+        id="raw-at-sign-in-password",
+    ),
+    pytest.param(
+        "socks5://:tokenz@proxy:1080",
+        "tokenz",
+        id="password-with-no-username",
+    ),
+    pytest.param(
+        "CalledProcessError: ['yt-dlp', '--proxy', 'http://u:p4ss@h:1']",
+        "p4ss",
+        id="argv-repr-from-subprocess",
+    ),
+]
+
+
+@pytest.mark.parametrize(("text", "secret"), LEAKED)
+def test_credentials_never_survive_redaction(redact, text, secret):
+    assert secret not in redact(text)
+
+
+def test_configured_proxy_host_is_preserved(redact):
+    """Operators must still be able to tell *which* proxy was in play."""
+    result = redact(f"failed via {_CONFIGURED}")
+    assert "proxy.internal:8080" in result
+    assert "s3cr3t" not in result
+
+
+# Text that must survive untouched -- over-redaction destroys diagnostics.
+PRESERVED = [
+    pytest.param("https://example.com/a@b", id="at-sign-in-path"),
+    pytest.param("https://example.com?e=a@b", id="at-sign-in-query"),
+    pytest.param("https://example.com#f=a@b", id="at-sign-in-fragment"),
+    pytest.param("connect to proxy.internal:8080 failed", id="bare-host-port"),
+    pytest.param("mailto is not a url: a@b.com", id="bare-email"),
+]
+
+
+@pytest.mark.parametrize("text", PRESERVED)
+def test_non_credential_text_is_untouched(redact, text):
+    assert redact(text) == text
+
+
+def test_match_never_spans_two_urls(redact):
+    """A greedy class must not swallow the gap between separate URLs."""
+    result = redact("http://a:1@h1:1 and http://b:2@h2:2")
+    assert result == "http://***:***@h1:1 and http://***:***@h2:2"
+
+
+def test_redaction_is_a_noop_when_no_proxy_configured(redact, monkeypatch):
+    """The generic sweep still applies with no WEBSHARE_PROXY_URL set."""
+    monkeypatch.delenv(_PROXY_ENV_VAR, raising=False)
+    assert "hunter2" not in redact("http://bob:hunter2@corp.proxy:3128")
+    assert redact("no credentials here") == "no credentials here"
+
+
+def test_hostile_str_does_not_propagate(redact):
+    """Called from except blocks -- raising here would mask the real error."""
+
+    class Hostile:
+        def __str__(self) -> str:
+            raise RuntimeError("boom")
+
+    assert redact(Hostile()) == "<unprintable error>"
+
+
+def test_non_string_input_is_stringified(redact):
+    assert redact(12345) == "12345"
+
+
+def test_exception_object_is_accepted(redact):
+    """The common call shape is redact(str(error)) -- accept the error too."""
+    assert "s3cr3t" not in redact(RuntimeError(f"boom via {_CONFIGURED}"))
diff --git a/uv.lock b/uv.lock
index 40d16cc8c..b98ee61f0 100644
--- a/uv.lock
+++ b/uv.lock
@@ -1237,7 +1237,7 @@ name = "cuda-bindings"
 version = "13.3.1"
 source = { registry = "https://pypi.org/simple" }
 dependencies = [
-    { name = "cuda-pathfinder" },
+    { name = "cuda-pathfinder", marker = "(python_full_version < '3.11' and sys_platform == 'emscripten') or (python_full_version < '3.11' and sys_platform == 'win32') or (python_full_version < '3.15' and sys_platform != 'emscripten' and sys_platform != 'win32')" },
 ]
 wheels = [
     { url = "https://files.pythonhosted.org/packages/a9/21/8464d133752951c154feafb3b65c297e7d80f301183d220bec4c830f1441/cuda_bindings-13.3.1-cp310-cp310-manylinux_2_24_aarch64.manylinux_2_28_aarch64.whl", hash = "sha256:120fcc53d57903df529c3486962c56528cba5b7d6c57c99537320ed9922c8b86", size = 6073403, upload-time = "2026-05-29T23:11:36.22Z" },
@@ -1272,43 +1272,43 @@ wheels = [
 
 [package.optional-dependencies]
 cublas = [
-    { name = "nvidia-cublas", marker = "platform_machine == 'aarch64' or platform_machine == 'x86_64'" },
-    { name = "nvidia-cuda-nvrtc", marker = "platform_machine == 'aarch64' or platform_machine == 'x86_64'" },
+    { name = "nvidia-cublas", marker = "(python_full_version < '3.11' and platform_machine == 'AMD64' and sys_platform == 'win32') or (platform_machine == 'aarch64' and sys_platform == 'linux') or (platform_machine == 'x86_64' and sys_platform == 'linux')" },
+    { name = "nvidia-cuda-nvrtc", marker = "(python_full_version < '3.11' and platform_machine == 'AMD64' and sys_platform == 'win32') or (platform_machine == 'aarch64' and sys_platform == 'linux') or (platform_machine == 'x86_64' and sys_platform == 'linux')" },
 ]
 cudart = [
-    { name = "nvidia-cuda-runtime", marker = "platform_machine == 'aarch64' or platform_machine == 'x86_64'" },
+    { name = "nvidia-cuda-runtime", marker = "(python_full_version < '3.11' and platform_machine == 'AMD64' and sys_platform == 'win32') or (platform_machine == 'aarch64' and sys_platform == 'linux') or (platform_machine == 'x86_64' and sys_platform == 'linux')" },
 ]
 cufft = [
-    { name = "nvidia-cufft", marker = "platform_machine == 'aarch64' or platform_machine == 'x86_64'" },
-    { name = "nvidia-nvjitlink", marker = "platform_machine == 'aarch64' or platform_machine == 'x86_64'" },
+    { name = "nvidia-cufft", marker = "(python_full_version < '3.11' and platform_machine == 'AMD64' and sys_platform == 'win32') or (platform_machine == 'aarch64' and sys_platform == 'linux') or (platform_machine == 'x86_64' and sys_platform == 'linux')" },
+    { name = "nvidia-nvjitlink", marker = "(python_full_version < '3.11' and platform_machine == 'AMD64' and sys_platform == 'win32') or (platform_machine == 'aarch64' and sys_platform == 'linux') or (platform_machine == 'x86_64' and sys_platform == 'linux')" },
 ]
 cufile = [
-    { name = "nvidia-cufile", marker = "platform_machine == 'aarch64' or platform_machine == 'x86_64'" },
+    { name = "nvidia-cufile", marker = "(platform_machine == 'aarch64' and sys_platform == 'linux') or (platform_machine == 'x86_64' and sys_platform == 'linux')" },
 ]
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