diff --git a/tests/proxy_behavior/management/test_key_share.py b/tests/proxy_behavior/management/test_key_share.py
index 3d869e38d9e..3475e302ed3 100644
--- a/tests/proxy_behavior/management/test_key_share.py
+++ b/tests/proxy_behavior/management/test_key_share.py
@@ -1,6 +1,10 @@
+import base64
+import json
 import os
 
+import httpx
 import pytest
+import respx
 
 from .actors import Actor
 
@@ -19,6 +23,19 @@ def _unconfigured_password_link(monkeypatch):
     monkeypatch.delenv("PASSWORD_LINK_API_KEY", raising=False)
 
 
+@pytest.fixture
+def force_httpx_transport(monkeypatch):
+    """Make the proxy's outbound HTTP client use httpx's transport so respx can
+    intercept the password.link call. litellm defaults to an aiohttp transport
+    that respx (an httpx tool) cannot see. Reset the cached client too so a fresh
+    httpx-backed one is built; monkeypatch restores both after the test."""
+    import litellm
+    from litellm.caching.llm_caching_handler import LLMClientCache
+
+    monkeypatch.setattr(litellm, "disable_aiohttp_transport", True)
+    monkeypatch.setattr(litellm, "in_memory_llm_clients_cache", LLMClientCache())
+
+
 async def test_key_share_requires_auth(proxy_client, world):
     resp = await proxy_client.post(
         "/key/share",
@@ -65,3 +82,46 @@ async def test_key_share_admin_reaches_config_gate(actor, proxy_client, world):
     )
     assert resp.status_code == 400, resp.text
     assert "password.link" in resp.text.lower()
+
+
+async def test_key_share_returns_link_and_never_uploads_plaintext(
+    proxy_client, world, monkeypatch, force_httpx_transport
+):
+    monkeypatch.setenv("PASSWORD_LINK_API_KEY", "private-test-key")
+    cleartext = world.keys[Actor.OWNER].cleartext
+
+    with respx.mock(assert_all_called=True) as mock:
+        route = mock.post("https://password.link/api/secrets").mock(
+            return_value=httpx.Response(201, json={"data": {"id": "abc123"}})
+        )
+        mock.route().pass_through()
+        resp = await proxy_client.post(
+            "/key/share",
+            headers={"Authorization": f"Bearer {world.keys[Actor.PROXY_ADMIN].cleartext}"},
+            json={"key": cleartext, "expiration_hours": 12, "max_views": 1},
+        )
+
+    assert resp.status_code == 200, resp.text
+    assert resp.json()["share_link"].startswith("https://password.link/?abc123#")
+
+    request_body = json.loads(route.calls.last.request.content)
+    assert route.calls.last.request.headers["authorization"] == "ApiKey private-test-key"
+    assert request_body["expiration"] == 12
+    assert cleartext not in json.dumps(request_body)
+    assert cleartext not in base64.b64decode(request_body["ciphertext"]).decode("utf-8")
+
+
+async def test_key_share_maps_upstream_failure_to_502(proxy_client, world, monkeypatch, force_httpx_transport):
+    monkeypatch.setenv("PASSWORD_LINK_API_KEY", "private-test-key")
+
+    with respx.mock(assert_all_called=True) as mock:
+        mock.post("https://password.link/api/secrets").mock(return_value=httpx.Response(402, text="quota exceeded"))
+        mock.route().pass_through()
+        resp = await proxy_client.post(
+            "/key/share",
+            headers={"Authorization": f"Bearer {world.keys[Actor.PROXY_ADMIN].cleartext}"},
+            json={"key": world.keys[Actor.OWNER].cleartext},
+        )
+
+    assert resp.status_code == 502, resp.text
+    assert "402" in resp.text