diff --git a/DockerfileLeanFoundation b/DockerfileLeanFoundation
index 64c6209db3cf..620e8cb5edd2 100644
--- a/DockerfileLeanFoundation
+++ b/DockerfileLeanFoundation
@@ -334,7 +334,10 @@ RUN conda install -c nvidia -y cuda-compiler=12.8.1 && conda clean -y --all
 ENV MKL_THREADING_LAYER=GNU
 ENV CUDA_MODULE_LOADING=LAZY
 ENV XLA_FLAGS=--xla_gpu_cuda_data_dir=/opt/miniconda3/
-ENV LD_LIBRARY_PATH=/opt/miniconda3/lib/python3.11/site-packages/nvidia/nvjitlink/lib/:/opt/miniconda3/lib/python3.11/site-packages/nvidia/cuda_nvrtc/lib/:$LD_LIBRARY_PATH
+# conda's OpenSSL first: .NET loads libssl/libcrypto by soname before python, and conda extensions then bind to that same copy,
+# which must be conda's. Only these two are linked so every other library keeps resolving as before
+RUN mkdir -p /opt/conda-openssl/lib && ln -s /opt/miniconda3/lib/libssl.so.3 /opt/miniconda3/lib/libcrypto.so.3 /opt/conda-openssl/lib/
+ENV LD_LIBRARY_PATH=/opt/conda-openssl/lib/:/opt/miniconda3/lib/python3.11/site-packages/nvidia/nvjitlink/lib/:/opt/miniconda3/lib/python3.11/site-packages/nvidia/cuda_nvrtc/lib/:$LD_LIBRARY_PATH
 # reduces GPU memory usage
 ENV PYTORCH_CUDA_ALLOC_CONF=expandable_segments:True
 
diff --git a/Tests/Python/PythonPackagesTests.cs b/Tests/Python/PythonPackagesTests.cs
index 10360f498a97..e745078601e6 100644
--- a/Tests/Python/PythonPackagesTests.cs
+++ b/Tests/Python/PythonPackagesTests.cs
@@ -15,6 +15,9 @@
 */
 
 using System;
+using System.IO;
+using System.Linq;
+using System.Security.Cryptography;
 using Python.Runtime;
 using NUnit.Framework;
 
@@ -2945,6 +2948,49 @@ import pandas as pd
     report = sv.analyze(df, target_feat='target')");
         }
 
+        [Test]
+        public void Cryptography()
+        {
+            AssertCode(@"
+from cryptography.fernet import Fernet
+
+def RunTest():
+    cipher = Fernet(Fernet.generate_key())
+    message = b'LEAN'
+    assert cipher.decrypt(cipher.encrypt(message)) == message");
+        }
+
+        // Runs first: a python extension loading the environment's libssl earlier would hide a wrong library search path
+        [Test, Order(1)]
+        public void DotNetLoadsPythonEnvironmentOpenSsl()
+        {
+            if (!OS.IsLinux)
+            {
+                Assert.Ignore("Only Linux resolves OpenSSL by soname");
+            }
+
+            // .NET loads libssl and libcrypto by soname, and python extensions loaded later bind to those same copies,
+            // so they need to be the python environment's, which its extensions were built against
+            SHA256.HashData(new byte[1]);
+
+            string pythonPrefix;
+            using (Py.GIL())
+            {
+                using var sys = Py.Import("sys");
+                // a virtual environment keeps using its base installation's native libraries
+                pythonPrefix = sys.GetAttr("base_prefix").As<string>();
+            }
+            var openSslLibraries = File.ReadLines("/proc/self/maps")
+                .Select(line => line.Split(' ', StringSplitOptions.RemoveEmptyEntries).Last())
+                .Where(path => path.Contains("/libssl.so") || path.Contains("/libcrypto.so"))
+                .Distinct()
+                .ToList();
+
+            Assert.IsNotEmpty(openSslLibraries);
+            Assert.IsTrue(openSslLibraries.All(path => path.StartsWith(pythonPrefix, StringComparison.InvariantCulture)),
+                $"OpenSSL loaded outside of {pythonPrefix}: {string.Join(", ", openSslLibraries)}");
+        }
+
         [TestCase("tf2onnx", "1.16.1", "__version__"), Explicit("These need to be run by themselves")]
         [TestCase("skl2onnx", "1.19.1", "__version__")]
         [TestCase("onnxmltools", "1.14.0", "__version__")]