diff --git a/litellm/proxy/auth/auth_checks.py b/litellm/proxy/auth/auth_checks.py
index 9a34167ad16..e8f335cb348 100644
--- a/litellm/proxy/auth/auth_checks.py
+++ b/litellm/proxy/auth/auth_checks.py
@@ -3587,13 +3587,16 @@ async def get_org_object_by_alias(
         )
 
 
+LITELLM_SESSION_TOKEN_PREFIX: Final = "litellm_login_"
+
+
 class ExperimentalUIJWTToken:
     @staticmethod
     def get_experimental_ui_login_jwt_auth_token(user_info: LiteLLM_UserTable) -> str:
         from datetime import timedelta
 
         from litellm.proxy.common_utils.encrypt_decrypt_utils import (
-            encrypt_value_helper,
+            encrypt_bearer_token,
         )
 
         if user_info.user_role is None:
@@ -3619,7 +3622,7 @@ class ExperimentalUIJWTToken:
             user_role=LitellmUserRoles(user_info.user_role),
         )
 
-        return encrypt_value_helper(valid_token.model_dump_json(exclude_none=True))
+        return encrypt_bearer_token(valid_token.model_dump_json(exclude_none=True), prefix=LITELLM_SESSION_TOKEN_PREFIX)
 
     @staticmethod
     def get_cli_jwt_auth_token(
@@ -3650,7 +3653,7 @@ class ExperimentalUIJWTToken:
         from datetime import timedelta
 
         from litellm.proxy.common_utils.encrypt_decrypt_utils import (
-            encrypt_value_helper,
+            encrypt_bearer_token,
         )
 
         if user_info.user_role is None:
@@ -3688,7 +3691,7 @@ class ExperimentalUIJWTToken:
             is_session_token=True,
         )
 
-        return encrypt_value_helper(valid_token.model_dump_json(exclude_none=True))
+        return encrypt_bearer_token(valid_token.model_dump_json(exclude_none=True), prefix=LITELLM_SESSION_TOKEN_PREFIX)
 
     @staticmethod
     def get_key_object_from_ui_hash_key(
@@ -3698,10 +3701,10 @@ class ExperimentalUIJWTToken:
 
         from litellm.proxy.auth.user_api_key_auth import UserAPIKeyAuth
         from litellm.proxy.common_utils.encrypt_decrypt_utils import (
-            decrypt_value_helper,
+            decrypt_bearer_token,
         )
 
-        decrypted_token: Final = decrypt_value_helper(hashed_token, key="ui_hash_key", exception_type="debug")
+        decrypted_token: Final = decrypt_bearer_token(hashed_token, prefix=LITELLM_SESSION_TOKEN_PREFIX)
         if decrypted_token is None:
             return None
         try:
diff --git a/litellm/proxy/common_utils/encrypt_decrypt_utils.py b/litellm/proxy/common_utils/encrypt_decrypt_utils.py
index 3584aaaf833..ae7240b8a7f 100644
--- a/litellm/proxy/common_utils/encrypt_decrypt_utils.py
+++ b/litellm/proxy/common_utils/encrypt_decrypt_utils.py
@@ -72,26 +72,55 @@ def _derive_key(signing_key: str) -> bytes:
     return hashlib.sha256(signing_key.encode()).digest()
 
 
-def _encrypt_aes_gcm(value: str, signing_key: str) -> str:
-    """Encrypt under AES-256-GCM and return the versioned ``v2:gcm:`` string."""
+def _seal_aes_gcm(value: str, signing_key: str, aad: bytes | None) -> bytes:
     from cryptography.hazmat.primitives.ciphers.aead import AESGCM
 
     nonce: Final = os.urandom(12)
     # AESGCM.encrypt returns ciphertext || tag(16); wire format is nonce || that.
-    blob: Final = AESGCM(_derive_key(signing_key)).encrypt(nonce, value.encode("utf-8"), None)
-    return _V2_GCM_PREFIX + base64.urlsafe_b64encode(nonce + blob).decode("utf-8")
+    return nonce + AESGCM(_derive_key(signing_key)).encrypt(nonce, value.encode("utf-8"), aad)
+
+
+def _open_aes_gcm(sealed: bytes, signing_key: str, aad: bytes | None) -> str:
+    from cryptography.hazmat.primitives.ciphers.aead import AESGCM
+
+    # An empty plaintext still serializes to nonce(12) || tag(16) = 28 bytes, so a
+    # short/empty buffer here is a corrupt value: let AESGCM.decrypt raise and be
+    # swallowed by the caller (returns None/original), same as legacy.
+    return AESGCM(_derive_key(signing_key)).decrypt(sealed[:12], sealed[12:], aad).decode("utf-8")
+
+
+def _encrypt_aes_gcm(value: str, signing_key: str) -> str:
+    """Encrypt under AES-256-GCM and return the versioned ``v2:gcm:`` string."""
+    sealed: Final = _seal_aes_gcm(value=value, signing_key=signing_key, aad=None)
+    return _V2_GCM_PREFIX + base64.urlsafe_b64encode(sealed).decode("utf-8")
 
 
 def _decrypt_aes_gcm(value: str, signing_key: str) -> str:
     """Decrypt a versioned ``v2:gcm:`` string produced by :func:`_encrypt_aes_gcm`."""
-    from cryptography.hazmat.primitives.ciphers.aead import AESGCM
+    sealed: Final = base64.urlsafe_b64decode(value[len(_V2_GCM_PREFIX) :])
+    return _open_aes_gcm(sealed=sealed, signing_key=signing_key, aad=None)
 
-    raw: Final = base64.urlsafe_b64decode(value[len(_V2_GCM_PREFIX) :])
-    # An empty plaintext still serializes to nonce(12) || tag(16) = 28 bytes, so a
-    # short/empty buffer here is a corrupt value: let AESGCM.decrypt raise and be
-    # swallowed by decrypt_value_helper (returns None/original), same as legacy.
-    nonce, blob = raw[:12], raw[12:]
-    return AESGCM(_derive_key(signing_key)).decrypt(nonce, blob, None).decode("utf-8")
+
+def encrypt_bearer_token(value: str, prefix: str) -> str:
+    """AES-256-GCM as unpadded base64url behind ``prefix``, which is also the AAD so a token can't change kind."""
+    salt_key: Final = _get_salt_key()
+    if not isinstance(salt_key, str):
+        raise ValueError("Set LITELLM_SALT_KEY or a master key to mint bearer tokens")
+    sealed: Final = _seal_aes_gcm(value=value, signing_key=salt_key, aad=prefix.encode("utf-8"))
+    return prefix + base64.urlsafe_b64encode(sealed).decode("ascii").rstrip("=")
+
+
+def decrypt_bearer_token(token: str, prefix: str) -> str | None:
+    """None unless ``token`` came from :func:`encrypt_bearer_token` with the same ``prefix``."""
+    salt_key: Final = _get_salt_key()
+    if not isinstance(salt_key, str) or not token.startswith(prefix):
+        return None
+    encoded: Final = token.removeprefix(prefix)
+    try:
+        sealed: Final = base64.b64decode(encoded + "=" * (-len(encoded) % 4), altchars=b"-_", validate=True)
+        return _open_aes_gcm(sealed=sealed, signing_key=salt_key, aad=prefix.encode("utf-8"))
+    except Exception:  # noqa: BLE001  # base64 and AES-GCM each raise their own "not a token" type
+        return None
 
 
 def encrypt_value_helper(value: str, new_encryption_key: str | None = None):
diff --git a/tests/e2e/CONTRIBUTING.md b/tests/e2e/CONTRIBUTING.md
index 8e221b2da5e..fb2cf2dfa24 100644
--- a/tests/e2e/CONTRIBUTING.md
+++ b/tests/e2e/CONTRIBUTING.md
@@ -64,7 +64,7 @@ The suites run against a live proxy, so bring one up first by running the litell
 
    For the opt-in browser profile, start the existing IdP first, then run `.github/e2e-stack/oidc-profile.sh "$PROXY_BASE_URL" <server-command>`. The wrapper creates a confidential client with an exact `/sso/callback` redirect and S256 PKCE, passes the client secret only through the child process environment, and removes the client on exit. It uses the existing generic OIDC handler with `GENERIC_USER_ID_ATTRIBUTE=sub`. Preserve the IdP's PostgreSQL data across restarts
 
-   `tests/e2e/ui/playwright.oidc.config.ts` uses an already running OIDC stack and separate storage/output files. Supply `E2E_OIDC_UI_URL`, `JWT_ISSUER`, `E2E_OIDC_USERNAME` and `E2E_OIDC_PASSWORD` for a seeded actor. Its setup follows the real login and callback path. The current Python canary qualifies browser-client configuration and token/userinfo identity mapping; browser journey specs under `ui/oidc/` are a separate coverage step
+   `tests/e2e/ui/playwright.oidc.config.ts` uses an already running OIDC stack and separate storage/output files. Supply `E2E_OIDC_UI_URL`, `JWT_ISSUER`, `E2E_OIDC_USERNAME` and `E2E_OIDC_PASSWORD` for a seeded actor. Its setup follows the real login and callback path. The current Python canary qualifies browser-client configuration and token/userinfo identity mapping. The specs under `ui/oidc/` drive a real dashboard SSO login and a real `lite login`, so start the proxy with `EXPERIMENTAL_UI_LOGIN=true` and at least one model it can actually serve. The CLI spec runs `lite` from `PATH` unless `E2E_LITE_CLI` names another executable, and it gives the CLI a temporary `HOME` with the keyring disabled so your own login is never touched. The main `playwright.config.ts` ignores `oidc/`
 
    Every successful IdP create immediately registers cleanup, including partial setup failures. Cleanup failures emit warnings. Tokens are minted on demand, and the expiration test waits relative to the token's actual `exp` with a bounded clock-drift check. To check first-attempt behavior locally, run both files with `--reruns 0`:
 
diff --git a/tests/e2e/coverage_registry/other.yaml b/tests/e2e/coverage_registry/other.yaml
index 3bd98ff5b0b..0b9249d7420 100644
--- a/tests/e2e/coverage_registry/other.yaml
+++ b/tests/e2e/coverage_registry/other.yaml
@@ -60,3 +60,6 @@
 
 - {id: other.auth.jwt.wrong_issuer_denied, module: other, tier: P0, area: auth, assertions: [wrong_issuer_denied], source: "auth/handle_jwt.py", rationale: "A signed token with the correct audience and an unexpected issuer is rejected"}
 - {id: other.auth.jwt.wrong_audience_denied, module: other, tier: P0, area: auth, assertions: [wrong_audience_denied], source: "auth/handle_jwt.py", rationale: "A signed token from the trusted issuer intended for another app is rejected"}
+- {id: other.auth.session_token.valid_allows, module: other, tier: P0, area: auth, assertions: [valid_allows], source: "auth/auth_checks.py ExperimentalUIJWTToken", rationale: "An unexpired LiteLLM-minted session token authenticates with the role it carries"}
+- {id: other.auth.session_token.expired_denied, module: other, tier: P0, area: auth, assertions: [expired_denied], source: "auth/user_api_key_auth.py expiry check", rationale: "An expired session token is rejected with the expired-key error"}
+- {id: other.auth.session_token.encrypted_value_denied, module: other, tier: P0, area: auth, assertions: [encrypted_value_denied], source: "auth/auth_checks.py ExperimentalUIJWTToken", rationale: "An encrypted value read back from a management route is not accepted as a bearer token"}
diff --git a/tests/e2e/other/test_session_token_e2e.py b/tests/e2e/other/test_session_token_e2e.py
new file mode 100644
index 00000000000..51791278026
--- /dev/null
+++ b/tests/e2e/other/test_session_token_e2e.py
@@ -0,0 +1,91 @@
+"""Live e2e: UI/CLI session tokens are accepted only while valid and only when minted as session tokens.
+
+The runner mints its own session tokens under the proxy's salt key, so the valid and expired cases run in
+seconds instead of waiting out a real login's expiry.
+"""
+
+from __future__ import annotations
+
+import base64
+import hashlib
+import json
+import os
+from datetime import datetime, timedelta, timezone
+from typing import Final
+
+import pytest
+from cryptography.hazmat.primitives.ciphers.aead import AESGCM
+from e2e_config import MASTER_KEY, unique_marker
+from e2e_http import UnauthorizedError, unwrap
+from lifecycle import ResourceManager
+from models import KeyGenerateBody, KeyLoggingCallback, KeyLoggingCallbackVars, KeyMetadata
+from other_client import OtherClient
+
+pytestmark = pytest.mark.e2e
+
+SALT_KEY: Final = os.environ.get("LITELLM_SALT_KEY") or MASTER_KEY
+SESSION_TOKEN_PREFIX: Final = "litellm_login_"
+ENCRYPTED_PREFIX: Final = "litellm_enc::"
+
+
+def _admin_session_token(expires_at: datetime) -> str:
+    claims: Final = json.dumps(
+        {
+            "token": f"ui-token-{unique_marker()}",
+            "user_id": f"e2e-session-{unique_marker()}",
+            "user_role": "proxy_admin",
+            "team_id": "litellm-dashboard",
+            "expires": expires_at.isoformat(),
+        }
+    )
+    nonce: Final = os.urandom(12)
+    sealed: Final = AESGCM(hashlib.sha256(SALT_KEY.encode()).digest()).encrypt(
+        nonce, claims.encode(), SESSION_TOKEN_PREFIX.encode()
+    )
+    return SESSION_TOKEN_PREFIX + base64.urlsafe_b64encode(nonce + sealed).decode().rstrip("=")
+
+
+class TestSessionToken:
+    @pytest.mark.covers("other.auth.session_token.valid_allows")
+    def test_unexpired_session_token_reaches_admin_route(self, client: OtherClient) -> None:
+        token: Final = _admin_session_token(datetime.now(timezone.utc) + timedelta(minutes=10))
+        listing: Final = unwrap(client.list_users_as(token))
+        assert listing.total >= 0, f"an unexpired admin session token did not reach /user/list: {listing}"
+
+    @pytest.mark.covers("other.auth.session_token.expired_denied")
+    def test_expired_session_token_is_denied(self, client: OtherClient) -> None:
+        token: Final = _admin_session_token(datetime.now(timezone.utc) - timedelta(minutes=1))
+        result: Final = client.list_users_as(token)
+        assert isinstance(result, UnauthorizedError), f"an expired session token must get 401, got {result}"
+        assert "expired" in result.body.lower(), f"expected the expired-key error, got {result.body[:300]}"
+
+    @pytest.mark.covers("other.auth.session_token.encrypted_value_denied")
+    def test_encrypted_stored_value_is_not_a_bearer_token(
+        self, client: OtherClient, resources: ResourceManager
+    ) -> None:
+        stored_value: Final = f'{{"token": "{unique_marker()}", "user_role": "proxy_admin"}}'
+        key: Final = client.proxy.generate_key(
+            KeyGenerateBody(
+                key_alias=f"e2e-session-{unique_marker()}",
+                metadata=KeyMetadata(
+                    logging=[
+                        KeyLoggingCallback(
+                            callback_name="langfuse",
+                            callback_vars=KeyLoggingCallbackVars(langfuse_secret_key=stored_value),
+                        )
+                    ]
+                ),
+            )
+        )
+        resources.defer(lambda: client.proxy.delete_key(key))
+
+        metadata: Final = client.proxy.key_info(key).metadata
+        assert metadata is not None and metadata.logging, f"/key/info dropped the logging metadata: {metadata}"
+        encrypted: Final = metadata.logging[0].callback_vars.langfuse_secret_key
+        assert encrypted is not None and encrypted.startswith(ENCRYPTED_PREFIX), (
+            f"expected /key/info to return the stored secret encrypted, got {encrypted!r}"
+        )
+
+        for bearer in (encrypted.removeprefix(ENCRYPTED_PREFIX), encrypted):
+            result = client.list_users_as(bearer)
+            assert isinstance(result, UnauthorizedError), f"an encrypted stored value must get 401, got {result}"
diff --git a/tests/e2e/ui/oidc/cliLogin.spec.ts b/tests/e2e/ui/oidc/cliLogin.spec.ts
new file mode 100644
index 00000000000..89b9a7c7439
--- /dev/null
+++ b/tests/e2e/ui/oidc/cliLogin.spec.ts
@@ -0,0 +1,87 @@
+import { expect, test } from "@playwright/test";
+import { execFile, spawn } from "node:child_process";
+import * as fs from "node:fs";
+import * as os from "node:os";
+import * as path from "node:path";
+import { promisify } from "node:util";
+
+const LITE_CLI = process.env.E2E_LITE_CLI ?? "lite";
+const SKIP_TEAM_SELECTION = "skip\n";
+const execFileAsync = promisify(execFile);
+
+function requiredEnv(name: string): string {
+  const value = process.env[name];
+  if (!value) throw new Error(`${name} must be set for the OIDC suite`);
+  return value;
+}
+
+test("CLI SSO login stores a session that lists models and completes a chat request", async ({ browser, baseURL }) => {
+  test.setTimeout(180_000);
+  const issuer = requiredEnv("JWT_ISSUER");
+  const home = fs.mkdtempSync(path.join(os.tmpdir(), "lite-cli-login-"));
+  const browserUrlFile = path.join(home, "browser-url");
+  const browserCommand = path.join(home, "browser.sh");
+  fs.writeFileSync(browserCommand, `#!/bin/sh\nprintf '%s' "$1" > '${browserUrlFile}'\n`, { mode: 0o700 });
+  const env = {
+    ...process.env,
+    HOME: home,
+    LITELLM_CLI_DISABLE_KEYRING: "1",
+    BROWSER: browserCommand,
+    PYTHONUNBUFFERED: "1",
+    FORCE_COLOR: undefined,
+    NO_COLOR: "1",
+    LITELLM_PROXY_URL: baseURL,
+    LITELLM_PROXY_API_KEY: undefined,
+  };
+  const login = spawn(LITE_CLI, ["login"], { env });
+  let loginOutput = "";
+  login.stdout.on("data", (chunk: Buffer) => (loginOutput += chunk.toString()));
+  login.stderr.on("data", (chunk: Buffer) => (loginOutput += chunk.toString()));
+  const loginExit = new Promise<number | null>((resolve) => login.on("close", resolve));
+  login.stdin.end(SKIP_TEAM_SELECTION);
+  try {
+    await expect.poll(() => fs.existsSync(browserUrlFile), { timeout: 30_000 }).toBe(true);
+    await expect.poll(() => loginOutput).toMatch(/Verification code: \S+/);
+    const userCode = /Verification code: (\S+)/.exec(loginOutput)?.[1] ?? "";
+
+    const context = await browser.newContext({ storageState: { cookies: [], origins: [] } });
+    try {
+      const page = await context.newPage();
+      await page.goto(fs.readFileSync(browserUrlFile, "utf8"));
+      await expect(page).toHaveURL((url) => url.href.startsWith(`${issuer}/`));
+      await page.getByLabel("Username or email").fill(requiredEnv("E2E_OIDC_USERNAME"));
+      await page.getByLabel("Password", { exact: true }).fill(requiredEnv("E2E_OIDC_PASSWORD"));
+      await page.getByRole("button", { name: "Sign In", exact: true }).click();
+      await page.getByLabel("Verification code").fill(userCode);
+      await page.getByRole("button", { name: "Continue", exact: true }).click();
+      await expect(page.getByRole("heading", { name: "Authentication Successful!" })).toBeVisible();
+    } finally {
+      await context.close();
+    }
+
+    expect(await loginExit, loginOutput).toBe(0);
+    expect(loginOutput).toContain("Login successful!");
+    const stored: { key?: unknown } = JSON.parse(fs.readFileSync(path.join(home, ".litellm", "token.json"), "utf8"));
+    expect(typeof stored.key).toBe("string");
+    expect(stored.key, "CLI login issues a session token, not a virtual key").not.toMatch(/^sk-/);
+
+    const { stdout: modelsJson } = await execFileAsync(LITE_CLI, ["models", "list", "--format", "json"], { env });
+    const models: { id: string }[] = JSON.parse(modelsJson);
+    expect(models.length, "the stack serves at least one model").toBeGreaterThan(0);
+
+    const chatRequest = JSON.stringify({
+      model: models[0].id,
+      messages: [{ role: "user", content: "Reply with the single word: ok" }],
+    });
+    const { stdout: completionJson } = await execFileAsync(
+      LITE_CLI,
+      ["http", "request", "POST", "/chat/completions", "-j", chatRequest],
+      { env },
+    );
+    const completion: { choices: { message: { content: string | null } }[] } = JSON.parse(completionJson);
+    expect(completion.choices[0]?.message.content).toBeTruthy();
+  } finally {
+    login.kill();
+    fs.rmSync(home, { recursive: true, force: true });
+  }
+});
diff --git a/tests/e2e/ui/oidc/dashboardLogin.spec.ts b/tests/e2e/ui/oidc/dashboardLogin.spec.ts
new file mode 100644
index 00000000000..106646949ed
--- /dev/null
+++ b/tests/e2e/ui/oidc/dashboardLogin.spec.ts
@@ -0,0 +1,35 @@
+import { expect, test, type Page as PlaywrightPage, type Response } from "@playwright/test";
+import { Page } from "../fixtures/pages";
+import { navigateToPage } from "../helpers/navigation";
+
+function sessionKey(tokenCookie: string): string {
+  const claims: unknown = JSON.parse(Buffer.from(tokenCookie.split(".")[1] ?? "", "base64url").toString("utf8"));
+  const key = claims !== null && typeof claims === "object" && "key" in claims ? claims.key : undefined;
+  if (typeof key !== "string") throw new Error("The dashboard token cookie carries no key claim");
+  return key;
+}
+
+async function openPageAndCapture(page: PlaywrightPage, target: Page, apiPath: string): Promise<Response> {
+  const response = page.waitForResponse((r) => new URL(r.url()).pathname === apiPath);
+  await navigateToPage(page, target);
+  return response;
+}
+
+test("SSO login issues a session that authorizes dashboard data requests", async ({ page, context, baseURL }) => {
+  const tokenCookie = (await context.cookies(baseURL)).find((cookie) => cookie.name === "token");
+  expect(tokenCookie, "SSO login sets the dashboard token cookie").toBeDefined();
+  const key = sessionKey(tokenCookie?.value ?? "");
+  expect(key, "SSO login issues a session token, not a virtual key").not.toMatch(/^sk-/);
+
+  const keyList = await openPageAndCapture(page, Page.ApiKeys, "/key/list");
+  expect(keyList.request().headers()["authorization"]).toBe(`Bearer ${key}`);
+  expect(keyList.status()).toBe(200);
+  expect(Array.isArray((await keyList.json()).keys)).toBe(true);
+
+  const modelInfo = await openPageAndCapture(page, Page.Models, "/v2/model/info");
+  expect(modelInfo.request().headers()["authorization"]).toBe(`Bearer ${key}`);
+  expect(modelInfo.status()).toBe(200);
+  const models: { model_name: string }[] = (await modelInfo.json()).data;
+  expect(models.length, "the stack serves at least one model").toBeGreaterThan(0);
+  await expect(page.getByText(models[0].model_name, { exact: true }).first()).toBeVisible();
+});
diff --git a/tests/e2e/ui/playwright.config.ts b/tests/e2e/ui/playwright.config.ts
index 2fc3b5f2d81..aed70620280 100644
--- a/tests/e2e/ui/playwright.config.ts
+++ b/tests/e2e/ui/playwright.config.ts
@@ -8,7 +8,7 @@ import { ARTIFACT_DIR, UI_BASE_URL } from "./constants";
 export default defineConfig({
   testDir: ".",
   testMatch: ["**/*.spec.ts", "**/*.setup.ts"],
-  testIgnore: ["**/*.test.*", "**/integrationCritical/**"],
+  testIgnore: ["**/*.test.*", "**/integrationCritical/**", "oidc/**"],
   /* Run tests in files in parallel */
   fullyParallel: true,
   /* Fail the build on CI if you accidentally left test.only in the source code. */
diff --git a/tests/test_litellm/proxy/auth/test_auth_checks.py b/tests/test_litellm/proxy/auth/test_auth_checks.py
index 9c8b95fd7e8..9803371c180 100644
--- a/tests/test_litellm/proxy/auth/test_auth_checks.py
+++ b/tests/test_litellm/proxy/auth/test_auth_checks.py
@@ -1,5 +1,7 @@
 import asyncio
+import base64
 import json
+import re
 import sys
 import time
 from collections.abc import Iterator, Mapping
@@ -38,6 +40,7 @@ from litellm.proxy._types import (
 from litellm.proxy.agent_endpoints.auth.agent_access_groups import AgentAccessGroupCeiling, CeilingResolver
 from litellm.types.agents import AgentCaller
 from litellm.proxy.auth.auth_checks import (
+    LITELLM_SESSION_TOKEN_PREFIX,
     ExperimentalUIJWTToken,
     _cache_management_object,
     _can_object_call_model,
@@ -76,7 +79,9 @@ from litellm.constants import (
     TAG_REGISTRY_MAX_SIZE,
 )
 from litellm.proxy.auth.route_checks import RouteChecks
-from litellm.proxy.common_utils.encrypt_decrypt_utils import decrypt_value_helper
+from litellm.proxy.auth.user_api_key_auth import check_api_key_for_custom_headers_or_pass_through_endpoints
+from litellm.proxy import proxy_server
+from litellm.proxy.common_utils.encrypt_decrypt_utils import decrypt_bearer_token, encrypt_value_helper
 from litellm.proxy.db.exception_handler import PrismaDBExceptionHandler
 from prisma.errors import DataError
 from litellm.proxy.common_utils.user_api_key_cache import (
@@ -149,7 +154,7 @@ def test_get_experimental_ui_login_jwt_auth_token_valid(valid_sso_user_defined_v
     token = ExperimentalUIJWTToken.get_experimental_ui_login_jwt_auth_token(valid_sso_user_defined_values)
 
     # Decrypt and verify token contents
-    decrypted_token = decrypt_value_helper(token, key="ui_hash_key", exception_type="debug")
+    decrypted_token = decrypt_bearer_token(token, prefix=LITELLM_SESSION_TOKEN_PREFIX)
     # Check that decrypted_token is not None before using json.loads
     assert decrypted_token is not None
     token_data = json.loads(decrypted_token)
@@ -175,7 +180,7 @@ def test_get_cli_jwt_auth_token_includes_team_alias(valid_sso_user_defined_value
         team_alias="test-team",
     )
 
-    decrypted_token = decrypt_value_helper(token, key="ui_hash_key", exception_type="debug")
+    decrypted_token = decrypt_bearer_token(token, prefix=LITELLM_SESSION_TOKEN_PREFIX)
     assert decrypted_token is not None
     token_data = json.loads(decrypted_token)
 
@@ -202,7 +207,7 @@ def test_get_cli_jwt_auth_token_carries_team_grants_not_user_allowlist(
         team_model_aliases={"team-fast": "gpt-4.1-mini"},
     )
 
-    decrypted_token = decrypt_value_helper(token, key="ui_hash_key", exception_type="debug")
+    decrypted_token = decrypt_bearer_token(token, prefix=LITELLM_SESSION_TOKEN_PREFIX)
     assert decrypted_token is not None
     token_data = json.loads(decrypted_token)
 
@@ -219,7 +224,7 @@ def test_get_cli_jwt_auth_token_keeps_user_allowlist_when_no_team(
     """A session token with no team bound still carries the user's own allowlist."""
     token = ExperimentalUIJWTToken.get_cli_jwt_auth_token(valid_sso_user_defined_values)
 
-    decrypted_token = decrypt_value_helper(token, key="ui_hash_key", exception_type="debug")
+    decrypted_token = decrypt_bearer_token(token, prefix=LITELLM_SESSION_TOKEN_PREFIX)
     assert decrypted_token is not None
     token_data = json.loads(decrypted_token)
 
@@ -233,7 +238,7 @@ def test_get_experimental_ui_login_jwt_auth_token_uses_10_min_expiry(
 ):
     """Test that Experimental UI token uses fixed 10-minute expiry (does not use LITELLM_UI_SESSION_DURATION)."""
     token = ExperimentalUIJWTToken.get_experimental_ui_login_jwt_auth_token(valid_sso_user_defined_values)
-    decrypted_token = decrypt_value_helper(token, key="ui_hash_key", exception_type="debug")
+    decrypted_token = decrypt_bearer_token(token, prefix=LITELLM_SESSION_TOKEN_PREFIX)
     assert decrypted_token is not None
     token_data = json.loads(decrypted_token)
     expires = datetime.fromisoformat(token_data["expires"].replace("Z", "+00:00"))
@@ -251,7 +256,7 @@ def test_experimental_ui_token_ignores_litellm_ui_session_duration(
     was incorrectly wired to the experimental flow."""
     # Default LITELLM_UI_SESSION_DURATION is "24h" - token must still expire in ~10 min
     token = ExperimentalUIJWTToken.get_experimental_ui_login_jwt_auth_token(valid_sso_user_defined_values)
-    decrypted_token = decrypt_value_helper(token, key="ui_hash_key", exception_type="debug")
+    decrypted_token = decrypt_bearer_token(token, prefix=LITELLM_SESSION_TOKEN_PREFIX)
     assert decrypted_token is not None
     token_data = json.loads(decrypted_token)
     expires = datetime.fromisoformat(token_data["expires"].replace("Z", "+00:00"))
@@ -288,6 +293,51 @@ def test_get_key_object_from_ui_hash_key_valid(valid_sso_user_defined_values, mo
     assert key_object.max_budget == litellm.max_ui_session_budget
 
 
+@pytest.mark.parametrize("encryption_algorithm", ["xsalsa20-poly1305", "aes-256-gcm"])
+def test_get_key_object_from_ui_hash_key_accepts_only_minted_session_tokens(
+    valid_sso_user_defined_values, monkeypatch, encryption_algorithm
+):
+    monkeypatch.setattr(proxy_server, "general_settings", {"encryption_algorithm": encryption_algorithm})
+    session_token = ExperimentalUIJWTToken.get_cli_jwt_auth_token(valid_sso_user_defined_values)
+    stored_value = encrypt_value_helper(json.dumps({"user_role": LitellmUserRoles.PROXY_ADMIN.value}))
+
+    key_object = ExperimentalUIJWTToken.get_key_object_from_ui_hash_key(session_token)
+    assert key_object is not None
+    assert key_object.user_role == LitellmUserRoles.PROXY_ADMIN
+    reshaped = LITELLM_SESSION_TOKEN_PREFIX + stored_value.removeprefix("v2:gcm:").rstrip("=")
+    for candidate in (stored_value, reshaped):
+        assert ExperimentalUIJWTToken.get_key_object_from_ui_hash_key(candidate) is None
+
+
+def test_session_tokens_are_header_safe_and_never_look_like_virtual_keys(valid_sso_user_defined_values):
+    for token in (
+        ExperimentalUIJWTToken.get_experimental_ui_login_jwt_auth_token(valid_sso_user_defined_values),
+        ExperimentalUIJWTToken.get_cli_jwt_auth_token(valid_sso_user_defined_values),
+    ):
+        assert re.fullmatch(r"litellm_login_[A-Za-z0-9_-]+", token), token
+        assert ExperimentalUIJWTToken.get_key_object_from_ui_hash_key(token) is not None
+
+
+@pytest.mark.asyncio
+async def test_session_token_survives_langfuse_basic_auth_parsing(valid_sso_user_defined_values):
+    session_token = ExperimentalUIJWTToken.get_cli_jwt_auth_token(valid_sso_user_defined_values)
+    basic_credentials = base64.b64encode(f"{session_token}:sk-lf-secret".encode()).decode()
+    request = MagicMock()
+    request.headers = {}
+
+    api_key = await check_api_key_for_custom_headers_or_pass_through_endpoints(
+        request=request,
+        route="/api/public/ingestion",
+        pass_through_endpoints=[
+            {"path": "/api/public/ingestion", "target": "https://example.com", "custom_auth_parser": "langfuse"}
+        ],
+        api_key=f"Basic {basic_credentials}",
+    )
+
+    assert api_key == session_token
+    assert ExperimentalUIJWTToken.get_key_object_from_ui_hash_key(session_token) is not None
+
+
 def test_get_key_object_from_ui_hash_key_invalid():
     """Test getting key object from invalid UI hash key"""
     # Test with invalid token
@@ -801,7 +851,7 @@ def test_get_cli_jwt_auth_token_default_expiration(valid_sso_user_defined_values
     token = ExperimentalUIJWTToken.get_cli_jwt_auth_token(valid_sso_user_defined_values)
 
     # Decrypt and verify token contents
-    decrypted_token = decrypt_value_helper(token, key="ui_hash_key", exception_type="debug")
+    decrypted_token = decrypt_bearer_token(token, prefix=LITELLM_SESSION_TOKEN_PREFIX)
     assert decrypted_token is not None
     token_data = json.loads(decrypted_token)
 
@@ -841,7 +891,7 @@ def test_get_cli_jwt_auth_token_custom_expiration(valid_sso_user_defined_values,
     token = auth_checks.ExperimentalUIJWTToken.get_cli_jwt_auth_token(valid_sso_user_defined_values)
 
     # Decrypt and verify token contents
-    decrypted_token = decrypt_value_helper(token, key="ui_hash_key", exception_type="debug")
+    decrypted_token = decrypt_bearer_token(token, prefix=LITELLM_SESSION_TOKEN_PREFIX)
     assert decrypted_token is not None
     token_data = json.loads(decrypted_token)
 
@@ -859,7 +909,7 @@ def test_get_cli_jwt_auth_token_unique_per_session(valid_sso_user_defined_values
     from litellm.constants import CLI_SESSION_KEY_PREFIX
 
     def _decode(token: str) -> dict:
-        decrypted = decrypt_value_helper(token, key="ui_hash_key", exception_type="debug")
+        decrypted = decrypt_bearer_token(token, prefix=LITELLM_SESSION_TOKEN_PREFIX)
         assert decrypted is not None
         return json.loads(decrypted)
 
@@ -879,7 +929,7 @@ def test_get_cli_jwt_auth_token_applies_fallback_budget(valid_sso_user_defined_v
     token = ExperimentalUIJWTToken.get_cli_jwt_auth_token(
         valid_sso_user_defined_values, max_budget=litellm.max_ui_session_budget
     )
-    decrypted = decrypt_value_helper(token, key="ui_hash_key", exception_type="debug")
+    decrypted = decrypt_bearer_token(token, prefix=LITELLM_SESSION_TOKEN_PREFIX)
     assert decrypted is not None
     assert json.loads(decrypted).get("max_budget") == litellm.max_ui_session_budget
 
@@ -888,7 +938,7 @@ def test_get_cli_jwt_auth_token_no_fallback_when_budget_provided(
     valid_sso_user_defined_values,
 ):
     token = ExperimentalUIJWTToken.get_cli_jwt_auth_token(valid_sso_user_defined_values, max_budget=None)
-    decrypted = decrypt_value_helper(token, key="ui_hash_key", exception_type="debug")
+    decrypted = decrypt_bearer_token(token, prefix=LITELLM_SESSION_TOKEN_PREFIX)
     assert decrypted is not None
     assert json.loads(decrypted).get("max_budget") is None
 
diff --git a/tests/test_litellm/proxy/common_utils/test_encrypt_decrypt_utils.py b/tests/test_litellm/proxy/common_utils/test_encrypt_decrypt_utils.py
index 9c07242bd23..5b7d35c3b46 100644
--- a/tests/test_litellm/proxy/common_utils/test_encrypt_decrypt_utils.py
+++ b/tests/test_litellm/proxy/common_utils/test_encrypt_decrypt_utils.py
@@ -7,14 +7,17 @@ gate, and the backward-compatibility guarantees that let legacy XSalsa20-Poly130
 """
 
 import base64
+import re
 
 import pytest
 
 from litellm.proxy import proxy_server
 from litellm.proxy.common_utils.encrypt_decrypt_utils import (
     _V2_GCM_PREFIX,
+    decrypt_bearer_token,
     decrypt_if_encrypted_with,
     decrypt_value_helper,
+    encrypt_bearer_token,
     encrypt_value,
     encrypt_value_helper,
 )
@@ -236,3 +239,30 @@ def test_explicit_key_decrypt_supports_the_empty_master_key():
     written_with_empty_key = encrypt_value(value="stored-secret", signing_key="")
 
     assert decrypt_if_encrypted_with(base64.urlsafe_b64encode(written_with_empty_key).decode(), "") == "stored-secret"
+
+
+def test_bearer_token_opens_only_under_its_own_prefix():
+    token = encrypt_bearer_token("session", prefix="kind_a_")
+    relabeled = "kind_b_" + token.removeprefix("kind_a_")
+
+    assert decrypt_bearer_token(token, prefix="kind_a_") == "session"
+    assert decrypt_bearer_token(token, prefix="kind_b_") is None
+    assert decrypt_bearer_token(relabeled, prefix="kind_b_") is None
+
+
+@pytest.mark.parametrize("use_aes", [False, True])
+def test_stored_value_is_not_a_bearer_token_even_when_reshaped(monkeypatch, use_aes: bool):
+    if use_aes:
+        _use_aes(monkeypatch)
+    stored = encrypt_value_helper("stored-secret")
+
+    for candidate in (stored, "kind_a_" + stored.removeprefix(_V2_GCM_PREFIX).rstrip("=")):
+        assert decrypt_bearer_token(candidate, prefix="kind_a_") is None
+
+
+@pytest.mark.parametrize("length", range(6))
+def test_bearer_token_uses_only_header_safe_characters(length: int):
+    token = encrypt_bearer_token("x" * length, prefix="kind_a_")
+
+    assert re.fullmatch(r"kind_a_[A-Za-z0-9_-]+", token), token
+    assert decrypt_bearer_token(token, prefix="kind_a_") == "x" * length