diff --git a/.github/workflows/ci.yml b/.github/workflows/ci.yml
index ef26a0b2bb..5e2e758ecd 100644
--- a/.github/workflows/ci.yml
+++ b/.github/workflows/ci.yml
@@ -223,6 +223,7 @@ jobs:
         env:
           LSP: '${{ matrix.lsp }}'
           LSP_EXTRACT_FILE: '${{ matrix.lsp_extract_file }}'
+          SKIP_SSL_INSTALLATION: "${{ matrix.arch == 'x86' && 1 || 0 }}"
       - if: always()
         uses: codecov/codecov-action@v7
         with:
diff --git a/ci.sh b/ci.sh
index 9362dbc727..d8d1094699 100755
--- a/ci.sh
+++ b/ci.sh
@@ -54,8 +54,13 @@ if [ "${NO_TEST_REQUIREMENTS-0}" == 1 ]; then
     python -m uv pip install pytest coverage -c test-requirements.txt
     flags="--skip-optional-imports"
 else
-    python -m uv pip install -r test-requirements.txt --no-deps
     flags=""
+    if [ "${SKIP_SSL_INSTALLATION-0}" == 1 ]; then
+        echo cryptography >excluded_deps
+        PIP_ARGS="--exclude excluded_deps"
+        flags="--skip-ssl-imports"
+    fi
+    python -m uv pip install -r test-requirements.txt --no-deps $PIP_ARGS
 fi
 
 # If we're testing with a LSP installed, then it might break network
diff --git a/src/trio/_tests/pytest_plugin.py b/src/trio/_tests/pytest_plugin.py
index bbb5093be5..b929ae3a73 100644
--- a/src/trio/_tests/pytest_plugin.py
+++ b/src/trio/_tests/pytest_plugin.py
@@ -9,6 +9,7 @@
 
 RUN_SLOW = True
 SKIP_OPTIONAL_IMPORTS = False
+SKIP_SSL_IMPORTS = False
 
 
 def pytest_addoption(parser: pytest.Parser) -> None:
@@ -18,13 +19,18 @@ def pytest_addoption(parser: pytest.Parser) -> None:
         action="store_true",
         help="skip tests that rely on libraries not required by trio itself",
     )
+    parser.addoption(
+        "--skip-ssl-imports",
+        action="store_true",
+        help="skip tests that rely on cryptography",
+    )
 
 
 def pytest_configure(config: pytest.Config) -> None:
-    global RUN_SLOW
+    global RUN_SLOW, SKIP_OPTIONAL_IMPORTS, SKIP_SSL_IMPORTS
     RUN_SLOW = config.getoption("--run-slow", default=True)
-    global SKIP_OPTIONAL_IMPORTS
     SKIP_OPTIONAL_IMPORTS = config.getoption("--skip-optional-imports", default=False)
+    SKIP_SSL_IMPORTS = config.getoption("--skip-ssl-imports", default=False)
 
 
 @pytest.fixture
@@ -47,8 +53,8 @@ def pytest_pyfunc_call(pyfuncitem: pytest.Function) -> None:
         pyfuncitem.obj = trio_test(pyfuncitem.obj)
 
 
-def skip_if_optional_else_raise(error: ImportError) -> NoReturn:
-    if SKIP_OPTIONAL_IMPORTS:
+def maybe_ignore_import_error(error: ImportError) -> NoReturn:
+    if SKIP_OPTIONAL_IMPORTS or (SKIP_SSL_IMPORTS and error.name == "cryptography"):
         pytest.skip(error.msg, allow_module_level=True)
     else:  # pragma: no cover
         raise error
diff --git a/src/trio/_tests/test_dtls.py b/src/trio/_tests/test_dtls.py
index 99cb68f11f..5a34d8c811 100644
--- a/src/trio/_tests/test_dtls.py
+++ b/src/trio/_tests/test_dtls.py
@@ -8,13 +8,13 @@
 import attrs
 import pytest
 
-from trio._tests.pytest_plugin import skip_if_optional_else_raise
+from trio._tests.pytest_plugin import maybe_ignore_import_error
 
 try:
     import trustme
     from OpenSSL import SSL
 except ImportError as error:
-    skip_if_optional_else_raise(error)
+    maybe_ignore_import_error(error)
 
 
 import trio
diff --git a/src/trio/_tests/test_exports.py b/src/trio/_tests/test_exports.py
index 1c2b46ca47..9a1f8451f4 100644
--- a/src/trio/_tests/test_exports.py
+++ b/src/trio/_tests/test_exports.py
@@ -19,7 +19,7 @@
 
 import trio
 import trio.testing
-from trio._tests.pytest_plugin import RUN_SLOW, skip_if_optional_else_raise
+from trio._tests.pytest_plugin import RUN_SLOW, maybe_ignore_import_error
 
 from .. import _core, _util
 from .._core._tests.tutil import slow
@@ -41,7 +41,7 @@ def _ensure_mypy_cache_updated() -> None:
     try:
         from mypy.api import run
     except ImportError as error:
-        skip_if_optional_else_raise(error)
+        maybe_ignore_import_error(error)
 
     global mypy_cache_updated
     if not mypy_cache_updated:
@@ -159,7 +159,7 @@ def no_underscores(symbols: Iterable[str]) -> set[str]:
         try:
             from pylint.lint import PyLinter
         except ImportError as error:
-            skip_if_optional_else_raise(error)
+            maybe_ignore_import_error(error)
 
         linter = PyLinter()
         assert module.__file__ is not None
@@ -172,7 +172,7 @@ def no_underscores(symbols: Iterable[str]) -> set[str]:
         try:
             import jedi
         except ImportError as error:
-            skip_if_optional_else_raise(error)
+            maybe_ignore_import_error(error)
 
         # Simulate typing "import trio; trio.<TAB>"
         script = jedi.Script(f"import {modname}; {modname}.")
@@ -215,7 +215,7 @@ def no_underscores(symbols: Iterable[str]) -> set[str]:
         try:
             import pyright  # noqa: F401
         except ImportError as error:
-            skip_if_optional_else_raise(error)
+            maybe_ignore_import_error(error)
         import subprocess
 
         res = subprocess.run(
@@ -380,7 +380,7 @@ def lookup_symbol(symbol: str) -> dict[str, Any]:  # type: ignore[misc, explicit
             try:
                 import jedi
             except ImportError as error:
-                skip_if_optional_else_raise(error)
+                maybe_ignore_import_error(error)
 
             script = jedi.Script(
                 f"from {module_name} import {class_name}; {class_name}.",
diff --git a/src/trio/_tests/test_ssl.py b/src/trio/_tests/test_ssl.py
index 8eb0659270..f0dd884c64 100644
--- a/src/trio/_tests/test_ssl.py
+++ b/src/trio/_tests/test_ssl.py
@@ -13,7 +13,7 @@
 import pytest
 
 from trio import StapledStream
-from trio._tests.pytest_plugin import skip_if_optional_else_raise
+from trio._tests.pytest_plugin import maybe_ignore_import_error
 from trio.abc import ReceiveStream, SendStream
 from trio.testing import MemoryReceiveStream, MemorySendStream
 
@@ -21,7 +21,7 @@
     import trustme
     from OpenSSL import SSL
 except ImportError as error:
-    skip_if_optional_else_raise(error)
+    maybe_ignore_import_error(error)
 
 import trio
 
diff --git a/src/trio/_tests/tools/test_gen_exports.py b/src/trio/_tests/tools/test_gen_exports.py
index 81e6d5f18f..3b923ed83d 100644
--- a/src/trio/_tests/tools/test_gen_exports.py
+++ b/src/trio/_tests/tools/test_gen_exports.py
@@ -4,14 +4,14 @@
 
 import pytest
 
-from trio._tests.pytest_plugin import skip_if_optional_else_raise
+from trio._tests.pytest_plugin import maybe_ignore_import_error
 
 # imports in gen_exports that are not in `install_requires` in setup.py
 try:
     import astor  # noqa: F401
     import isort  # noqa: F401
 except ImportError as error:
-    skip_if_optional_else_raise(error)
+    maybe_ignore_import_error(error)
 
 
 from trio._tools.gen_exports import (
@@ -103,7 +103,7 @@ def test_process(
         import black  # noqa: F401
     # there's no dedicated CI run that has astor+isort, but lacks black.
     except ImportError as error:  # pragma: no cover
-        skip_if_optional_else_raise(error)
+        maybe_ignore_import_error(error)
 
     modpath = tmp_path / "_module.py"
     genpath = tmp_path / "_generated_module.py"
@@ -141,7 +141,7 @@ def test_run_ruff(tmp_path: Path) -> None:
     try:
         import ruff  # noqa: F401
     except ImportError as error:  # pragma: no cover
-        skip_if_optional_else_raise(error)
+        maybe_ignore_import_error(error)
 
     file = File(tmp_path / "module.py", "module")
 
@@ -168,7 +168,7 @@ def test_lint_failure(tmp_path: Path) -> None:
         import black  # noqa: F401
         import ruff  # noqa: F401
     except ImportError as error:  # pragma: no cover
-        skip_if_optional_else_raise(error)
+        maybe_ignore_import_error(error)
 
     file = File(tmp_path / "module.py", "module")
 
diff --git a/src/trio/_tests/tools/test_sync_requirements.py b/src/trio/_tests/tools/test_sync_requirements.py
index 92b3bfdd97..5beb707558 100644
--- a/src/trio/_tests/tools/test_sync_requirements.py
+++ b/src/trio/_tests/tools/test_sync_requirements.py
@@ -2,13 +2,13 @@
 
 from typing import TYPE_CHECKING
 
-from trio._tests.pytest_plugin import skip_if_optional_else_raise
+from trio._tests.pytest_plugin import maybe_ignore_import_error
 
 # imports in gen_exports that are not in `install_requires` in requirements
 try:
     import yaml  # noqa: F401
 except ImportError as error:
-    skip_if_optional_else_raise(error)
+    maybe_ignore_import_error(error)
 
 from trio._tools.sync_requirements import (
     update_requirements,
diff --git a/test-requirements.txt b/test-requirements.txt
index 96e65ac31d..80c2bf538b 100644
--- a/test-requirements.txt
+++ b/test-requirements.txt
@@ -39,7 +39,7 @@ colorama==0.4.6 ; sys_platform == 'win32'
     #   sphinx
 coverage==7.16.0
     # via -r test-requirements.in
-cryptography==48.0.0
+cryptography==50.0.1
     # via
     #   -r test-requirements.in
     #   pyopenssl
@@ -126,7 +126,7 @@ pygments==2.21.0
     #   sphinx
 pylint==4.0.8
     # via -r test-requirements.in
-pyopenssl==26.2.0
+pyopenssl==26.4.0
     # via -r test-requirements.in
 pyright==1.1.411
     # via -r test-requirements.in