diff --git a/src/specify_cli/__init__.py b/src/specify_cli/__init__.py
index 93f10a1950..44a029b93b 100644
--- a/src/specify_cli/__init__.py
+++ b/src/specify_cli/__init__.py
@@ -455,6 +455,7 @@ def version(
 ):
     """Display version and system information."""
     import platform
+    import ssl
 
     cli_version = get_speckit_version()
 
@@ -489,6 +490,12 @@ 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.
+    openssl_version = getattr(ssl, "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..4c42577c4e 100644
--- a/tests/test_cli_version.py
+++ b/tests/test_cli_version.py
@@ -1,6 +1,7 @@
 """Tests for CLI version reporting."""
 
 import json
+import ssl
 from unittest.mock import patch
 
 from typer.testing import CliRunner
@@ -77,3 +78,20 @@ 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