diff --git a/litellm/proxy/auth/cli_session_registry.py b/litellm/proxy/auth/cli_session_registry.py
index f66d5432d7a..4c6cc6e534e 100644
--- a/litellm/proxy/auth/cli_session_registry.py
+++ b/litellm/proxy/auth/cli_session_registry.py
@@ -6,7 +6,9 @@ it by decrypting it. This registry is the server-side record that makes a sessio
 listable and revocable: one row per login, keyed by the sha256 of the session token.
 
 A session with no row predates the registry and still authenticates until it expires;
-only a row with ``revoked_at`` set is refused.
+only a row with ``revoked_at`` set is refused. Expired rows are dead weight, so every
+registration drops them first and the table stays bounded by the number of live
+sessions rather than by every login ever made.
 """
 
 from __future__ import annotations
@@ -49,6 +51,8 @@ class _CLISessionTable(Protocol):
 
     async def update(self, where: Mapping[str, object], data: Mapping[str, object]) -> _CLISessionRecord | None: ...
 
+    async def delete_many(self, where: Mapping[str, object]) -> int: ...
+
 
 def _cli_session_table(prisma_client: PrismaClient) -> _CLISessionTable:
     table: Final[_CLISessionTable] = CLISessionRepository(prisma_client).table
@@ -71,9 +75,14 @@ async def record_cli_session(
     user_id: str,
     team_id: str | None,
 ) -> CLISessionResponse:
-    """Register a freshly minted session. Raises if the row cannot be written, so a
-    session that could never be revoked is never handed to the CLI."""
-    created: Final = await _cli_session_table(prisma_client).create(
+    """Register a freshly minted session, first dropping rows that can no longer be
+    revoked. Raises if the row cannot be written, so a session that could never be
+    revoked is never handed to the CLI."""
+    table: Final = _cli_session_table(prisma_client)
+    await table.delete_many(
+        where={"expires_at": {"lte": get_utc_datetime()}}  # mutable-ok: prisma query filters are dict-shaped
+    )
+    created: Final = await table.create(
         data={  # mutable-ok: prisma payloads are plain dicts
             "session_id": cli_session_id(session_token),
             "user_id": user_id,
diff --git a/tests/test_litellm/proxy/auth/test_cli_session_registry.py b/tests/test_litellm/proxy/auth/test_cli_session_registry.py
index 844fd0cdbde..d7ba4012dd7 100644
--- a/tests/test_litellm/proxy/auth/test_cli_session_registry.py
+++ b/tests/test_litellm/proxy/auth/test_cli_session_registry.py
@@ -71,6 +71,13 @@ class FakeCLISessionTable:
         gt = where["expires_at"]["gt"]
         return len([r for r in self.rows.values() if r["expires_at"] > gt])
 
+    async def delete_many(self, where):
+        lte = where["expires_at"]["lte"]
+        doomed = [sid for sid, r in self.rows.items() if r["expires_at"] <= lte]
+        for sid in doomed:
+            del self.rows[sid]
+        return len(doomed)
+
 
 class FakeDB:
     def __init__(self, table):
@@ -321,6 +328,29 @@ async def test_db_outage_follows_the_proxy_wide_posture(monkeypatch):
         await is_cli_session_revoked(session_token=SESSION_TOKEN, prisma_client=prisma, user_api_key_cache=_cache())
 
 
+@pytest.mark.asyncio
+async def test_recording_drops_expired_sessions_but_keeps_live_ones():
+    """An authenticated user can log in over and over. Without a retention path every
+    login would leave a row behind forever, so registration must clear the rows that
+    can no longer be revoked while leaving every live session listable."""
+    table = FakeCLISessionTable(
+        {
+            "dead-1": _session_row(session_id="dead-1", expires_in_hours=-5),
+            "dead-2": _session_row(session_id="dead-2", expires_in_hours=-1),
+            "live": _session_row(session_id="live", expires_in_hours=1),
+        }
+    )
+
+    await record_cli_session(
+        prisma_client=FakePrismaClient(table),
+        session_token=SESSION_TOKEN,
+        user_id="u-1",
+        team_id="t-1",
+    )
+
+    assert sorted(table.rows) == sorted(["live", hash_token(SESSION_TOKEN)])
+
+
 @pytest.mark.asyncio
 async def test_listing_hides_expired_sessions():
     table = FakeCLISessionTable(
diff --git a/tests/test_litellm/proxy/management_endpoints/test_ui_sso.py b/tests/test_litellm/proxy/management_endpoints/test_ui_sso.py
index d1832abe0f3..22f1c681fb4 100644
--- a/tests/test_litellm/proxy/management_endpoints/test_ui_sso.py
+++ b/tests/test_litellm/proxy/management_endpoints/test_ui_sso.py
@@ -2528,6 +2528,7 @@ def _cli_session_registry_prisma() -> MagicMock:
     the credential out, so the poll needs a DB whose CLI-session table accepts the write."""
     prisma = MagicMock()
     now = datetime.now(timezone.utc)
+    prisma.db.litellm_clisessiontable.delete_many = AsyncMock(return_value=0)
     prisma.db.litellm_clisessiontable.create = AsyncMock(
         return_value=SimpleNamespace(
             model_dump=lambda: {