diff --git a/appdaemon/adapi.py b/appdaemon/adapi.py
index aba26b6f2..ea098276d 100644
--- a/appdaemon/adapi.py
+++ b/appdaemon/adapi.py
@@ -14,9 +14,8 @@
 from pathlib import Path
 from typing import TYPE_CHECKING, Any, Literal, TypeVar, overload
 
-from appdaemon import dependency
+from appdaemon import dependency, utils
 from appdaemon import exceptions as ade
-from appdaemon import utils
 from appdaemon.appdaemon import AppDaemon
 from appdaemon.entity import Entity
 from appdaemon.events import EventCallback
@@ -24,6 +23,7 @@
 from appdaemon.models.config.app import AppConfig
 from appdaemon.parse import resolve_time_str
 from appdaemon.state import StateCallbackType
+
 from .types import TimeDeltaLike
 
 T = TypeVar("T")
@@ -3225,6 +3225,7 @@ async def run_every(
         start: str | dt.time | dt.datetime | None = None,
         interval: TimeDeltaLike = 0,
         *args,
+        immediate: bool = False,
         random_start: TimeDeltaLike | None = None,
         random_end: TimeDeltaLike | None = None,
         pin: bool | None = None,
@@ -3257,6 +3258,8 @@ async def run_every(
                 - If this is a ``timedelta`` object, the current date will be assumed.
 
             *args: Arbitrary positional arguments to be provided to the callback function when it is triggered.
+            immediate (bool, optional): Whether to immediately fire the callback or wait until the first interval if the
+                start time is now.
             random_start (int, optional): Start of range of the random time.
             random_end (int, optional): End of range of the random time.
             pin (bool, optional): Optional setting to override the default thread pinning behavior. By default, this is
@@ -3310,7 +3313,7 @@ def timed_callback(self, **kwargs): ...  # example callback
 
         """
         interval = utils.parse_timedelta(interval)
-        next_period = await self.AD.sched.get_next_period(interval, start)
+        next_period = await self.AD.sched.get_next_period(interval, start, immediate=immediate)
 
         self.logger.debug(
             "Registering %s for run_every in %s intervals, starting %s",
diff --git a/appdaemon/scheduler.py b/appdaemon/scheduler.py
index 5d1f0b0db..94a363a78 100644
--- a/appdaemon/scheduler.py
+++ b/appdaemon/scheduler.py
@@ -483,6 +483,8 @@ async def get_next_period(
         self,
         interval: TimeDeltaLike,
         start: time | datetime | str | None = None,
+        *,
+        immediate: bool = False,
     ) -> datetime:
         interval = utils.parse_timedelta(interval)
         start = "now" if start is None else start
@@ -493,7 +495,7 @@ async def get_next_period(
         assert isinstance(aware_start, datetime) and aware_start.tzinfo is not None
 
         # Skip forward to the next period if start is in the past
-        while aware_start < now:
+        while aware_start < now or (immediate and aware_start <= now):
             aware_start += interval
 
         return aware_start
@@ -901,7 +903,7 @@ async def parse_datetime(
         # Need to force timezone during time-travel mode
         if now is None:
             now = await self.get_now()
-        now = now.astimezone(self.AD.tz)
+        now = utils.ensure_timezone(now, self.AD.tz)
         return parse.parse_datetime(
             input_=input_,
             now=now,
diff --git a/docs/HISTORY.md b/docs/HISTORY.md
index 98f117ef8..3f65f1ef6 100644
--- a/docs/HISTORY.md
+++ b/docs/HISTORY.md
@@ -9,6 +9,7 @@
 - Reload modified apps on SIGUSR2 - contributed by [chatziko](https://github.com/chatziko)
 - Using urlib to create endpoints from URLs - contributed by [cebtenzzre](https://github.com/cebtenzzre)
 - Added {py:meth}`~appdaemon.plugins.hass.hassapi.Hass.process_conversation` and {py:meth}`~appdaemon.plugins.hass.hassapi.Hass.reload_conversation` to the {ref}`Hass API <hass-api-usage>`.
+- Added `immediate` kwargs to `run_every` to control semantics around `start == "now"`
 
 **Fixes**