diff --git a/litellm/proxy/proxy_server.py b/litellm/proxy/proxy_server.py
index f7a27e4896c..de98a4d571b 100644
--- a/litellm/proxy/proxy_server.py
+++ b/litellm/proxy/proxy_server.py
@@ -12453,7 +12453,7 @@ class ProxyStartupEvent:
                 _scheduled_weekly_spend_report,
                 "interval",
                 days=days,
-                next_run_time=datetime.now() + timedelta(seconds=10 + random.randint(0, 300)),
+                next_run_time=datetime.now(timezone.utc) + timedelta(seconds=10 + random.randint(0, 300)),
                 id=WEEKLY_SPEND_REPORT_JOB_ID,
                 replace_existing=True,
                 misfire_grace_time=APSCHEDULER_MISFIRE_GRACE_TIME,
diff --git a/pyproject.toml b/pyproject.toml
index e80ba2d5d44..76bb3a54223 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -74,6 +74,7 @@ proxy = [
     "hiredis>=3.0.0,<4.0; python_version < '3.15'",
     "hiredis>=3.5.0,<4.0; python_version >= '3.15'",
     "apscheduler>=3.11.2,<4.0",
+    "tzdata>=2024.1",
     "fastapi-sso>=0.19.0,<1.0",
     "PyJWT>=2.13.0,<3.0",
     "python-multipart>=0.0.27,<1.0",
diff --git a/tests/unit/proxy/proxy_server/test_lifecycle.py b/tests/unit/proxy/proxy_server/test_lifecycle.py
index db5be07fb6f..7f99d12c868 100644
--- a/tests/unit/proxy/proxy_server/test_lifecycle.py
+++ b/tests/unit/proxy/proxy_server/test_lifecycle.py
@@ -25,6 +25,7 @@ import os
 import subprocess
 from collections.abc import AsyncIterator, Awaitable, Callable
 from contextlib import asynccontextmanager
+from datetime import datetime, timedelta, timezone
 from typing import Final
 from unittest.mock import AsyncMock, MagicMock, patch
 
@@ -1393,6 +1394,25 @@ async def test_monthly_spend_report_sent_when_the_lock_is_free_or_absent(acquire
     proxy_logging_obj.slack_alerting_instance.send_monthly_spend_report.assert_awaited_once_with()
 
 
+@pytest.mark.asyncio
+async def test_weekly_spend_report_first_run_is_minutes_ahead_when_the_scheduler_zone_differs_from_the_clock():
+    """TZ=Asia/Calcutta on a host without the legacy alias puts the scheduler on IST through tzdata while
+    datetime.now() stays on UTC, so a naive first run landed hours in the past, past the misfire grace."""
+    local_offset: Final = datetime.now().astimezone().utcoffset() or timedelta(0)
+    scheduler: Final = AsyncIOScheduler(timezone=timezone(local_offset + timedelta(hours=5, minutes=30)))
+    registered_after: Final = datetime.now(timezone.utc)
+
+    await ProxyStartupEvent._initialize_slack_alerting_jobs(
+        scheduler=scheduler,
+        general_settings={},
+        proxy_logging_obj=_make_slack_alerting_proxy_logging(acquire_lock_result=True),
+        prisma_client=MagicMock(),
+    )
+
+    first_run: Final = scheduler.get_job("weekly_spend_report_job").next_run_time
+    assert registered_after < first_run < datetime.now(timezone.utc) + timedelta(seconds=311)
+
+
 @pytest.mark.asyncio
 async def test_spend_report_locks_are_never_released():
     """The lock is a per-window marker, not a mutex: releasing it lets the next pod re-send."""
diff --git a/tests/unit/test_package_metadata.py b/tests/unit/test_package_metadata.py
index dc6e3dca64e..d7dce33bd74 100644
--- a/tests/unit/test_package_metadata.py
+++ b/tests/unit/test_package_metadata.py
@@ -2,6 +2,7 @@ import sys
 from pathlib import Path
 from typing import Final
 
+import pytest
 from packaging.requirements import Requirement
 from packaging.specifiers import SpecifierSet
 from packaging.utils import NormalizedName, canonicalize_name
@@ -22,6 +23,11 @@ AIOHTTP_POOL_POISONING_SOURCE: Final = "aio-libs/aiohttp#12953, fixed in aiohttp
 ANYIO_STRANDED_LOCK_WAITER_FIX: Final = Version("4.14.0")
 ANYIO_STRANDED_LOCK_WAITER_SOURCE: Final = "agronholm/anyio#1145, fixed in anyio 4.14.0 released 2026-06-15"
 CLI_RUNTIME_DEPENDENCIES: Final = frozenset({"rich", "pyyaml", "requests"})
+PROXY_INSTALL_PLATFORMS: Final = (
+    ("linux", "Linux", "posix"),
+    ("darwin", "Darwin", "posix"),
+    ("win32", "Windows", "nt"),
+)
 PROXY_SERVER_ONLY_DEPENDENCIES: Final = frozenset(
     {
         "fastapi",
@@ -50,6 +56,20 @@ def _requirement_names(requirements: list[str]) -> frozenset[NormalizedName]:
     return frozenset(canonicalize_name(Requirement(requirement).name) for requirement in requirements)
 
 
+def _proxy_requirements_installed_on(sys_platform: str, platform_system: str, os_name: str) -> frozenset[NormalizedName]:
+    environment: Final = {
+        "sys_platform": sys_platform,
+        "platform_system": platform_system,
+        "os_name": os_name,
+        "extra": "proxy",
+    }
+    return frozenset(
+        canonicalize_name(requirement.name)
+        for requirement in map(Requirement, OPTIONAL_DEPENDENCIES["proxy"])
+        if requirement.marker is None or requirement.marker.evaluate(environment)
+    )
+
+
 def test_importing_litellm_reports_the_declared_release_version() -> None:
     import litellm
 
@@ -79,6 +99,15 @@ def test_cli_extra_is_a_thin_client_install() -> None:
     assert cli & PROXY_SERVER_ONLY_DEPENDENCIES == frozenset()
 
 
+@pytest.mark.parametrize(("sys_platform", "platform_system", "os_name"), PROXY_INSTALL_PLATFORMS)
+def test_proxy_extra_installs_tzdata_beside_its_scheduler_on_every_platform(
+    sys_platform: str, platform_system: str, os_name: str
+) -> None:
+    installed: Final = _proxy_requirements_installed_on(sys_platform, platform_system, os_name)
+    assert canonicalize_name("apscheduler") in installed
+    assert canonicalize_name("tzdata") in installed
+
+
 def test_declared_aiohttp_floor_excludes_pool_poisoning_releases() -> None:
     declared: Final = tuple(
         Requirement(requirement)
diff --git a/uv.lock b/uv.lock
index 2dec937800c..386f4339b3f 100644
--- a/uv.lock
+++ b/uv.lock
@@ -5138,6 +5138,7 @@ proxy = [
     { name = "soundfile" },
     { name = "starlette" },
     { name = "tomlkit" },
+    { name = "tzdata" },
     { name = "uvicorn" },
     { name = "uvloop", marker = "sys_platform != 'win32'" },
     { name = "websockets" },
@@ -5423,6 +5424,7 @@ requires-dist = [
     { name = "tomlkit", marker = "extra == 'cli'", specifier = ">=0.13.3,<1.0" },
     { name = "tomlkit", marker = "extra == 'proxy'", specifier = ">=0.13.3,<1.0" },
     { name = "typing-extensions", specifier = ">=4.13.0,<5.0" },
+    { name = "tzdata", marker = "extra == 'proxy'", specifier = ">=2024.1" },
     { name = "uvicorn", marker = "extra == 'proxy'", specifier = ">=0.33.0,<1.0" },
     { name = "uvloop", marker = "sys_platform != 'win32' and extra == 'proxy'", specifier = ">=0.22.1,<1.0" },
     { name = "websockets", marker = "extra == 'proxy'", specifier = ">=15.0.1,<16.0" },