diff --git a/src/specify_cli/__init__.py b/src/specify_cli/__init__.py
index 93f10a1950..fcc366a045 100644
--- a/src/specify_cli/__init__.py
+++ b/src/specify_cli/__init__.py
@@ -489,6 +489,18 @@ def version(
     info_table.add_row("Platform", platform.system())
     info_table.add_row("Architecture", platform.machine())
     info_table.add_row("OS Version", platform.version())
+    # The OpenSSL runtime the interpreter actually loaded. HTTPS failure
+    # reports (#4433) hinge on which OpenSSL is in play, and on Windows it is
+    # not obvious from the outside, so surface it here. An interpreter built
+    # without the ssl extension skips the row rather than failing the command.
+    try:
+        import ssl
+
+        openssl_version = getattr(ssl, "OPENSSL_VERSION", "")
+    except ImportError:
+        openssl_version = ""
+    if openssl_version:
+        info_table.add_row("OpenSSL", openssl_version)
 
     panel = Panel(
         info_table,
diff --git a/tests/test_cli_version.py b/tests/test_cli_version.py
index 041ff62e55..ae64fa53bc 100644
--- a/tests/test_cli_version.py
+++ b/tests/test_cli_version.py
@@ -1,6 +1,8 @@
 """Tests for CLI version reporting."""
 
 import json
+import ssl
+import sys
 from unittest.mock import patch
 
 from typer.testing import CliRunner
@@ -77,3 +79,43 @@ def test_version_json_requires_features(self):
 
         assert result.exit_code != 0
         assert "--json requires --features" in result.output
+
+    def test_version_reports_openssl_runtime(self):
+        """specify version reports the OpenSSL runtime the interpreter loaded.
+
+        Regression test for the triage gap in #4433: HTTPS failures on Windows
+        are commonly blamed on a PATH-preceded OpenSSL DLL, but ``specify
+        version`` reported no OpenSSL information at all, so a report had no way
+        to show which runtime was actually in use.
+        """
+        with patch("specify_cli.get_speckit_version", return_value="1.2.3"):
+            result = runner.invoke(app, ["version"])
+
+        assert result.exit_code == 0
+
+        expected = ssl.OPENSSL_VERSION
+        assert expected, "test host reports no ssl.OPENSSL_VERSION to assert against"
+        assert expected in result.output
+
+    def test_version_skips_openssl_row_when_ssl_unavailable(self, monkeypatch):
+        """An interpreter built without the ssl extension skips the OpenSSL row.
+
+        ``sys.modules["ssl"] = None`` makes ``import ssl`` raise ImportError,
+        simulating a build without ``_ssl``. The command must still succeed —
+        only the OpenSSL row is omitted.
+        """
+        monkeypatch.setitem(sys.modules, "ssl", None)
+        with patch("specify_cli.get_speckit_version", return_value="1.2.3"):
+            result = runner.invoke(app, ["version"])
+
+        assert result.exit_code == 0
+        assert "OpenSSL" not in result.output
+
+    def test_version_features_never_touches_ssl(self, monkeypatch):
+        """--features/--json return early and must not require ssl at all."""
+        monkeypatch.setitem(sys.modules, "ssl", None)
+        with patch("specify_cli.get_speckit_version", return_value="1.2.3"):
+            result = runner.invoke(app, ["version", "--features", "--json"])
+
+        assert result.exit_code == 0
+        assert json.loads(result.output)["version"] == "1.2.3"