diff --git a/matchy/cogs/matcher.py b/matchy/cogs/matcher.py
index 9734a2c..d8f9d39 100644
--- a/matchy/cogs/matcher.py
+++ b/matchy/cogs/matcher.py
@@ -92,8 +92,8 @@ class MatcherCog(commands.Cog):
             msg += "\n" + strings.paused_matchees(mentions) + "\n"
 
         tasks = state.State.get_channel_match_tasks(interaction.channel.id)
-        for (day, hour, min) in tasks:
-            next_run = util.get_next_datetime(day, hour)
+        for (day, hour, min, cadence, cadence_start) in tasks:
+            next_run = util.get_next_datetime_with_cadence(day, hour, datetime.now(), cadence, cadence_start)
             msg += "\n" + strings.scheduled(next_run, min)
 
         if not msg:
@@ -132,19 +132,19 @@ class MatcherCog(commands.Cog):
             return
 
         # Add the scheduled task and save
-        state.State.set_channel_match_task(
-            channel_id, members_min, weekday, hour, cadence)
+        (_, _, _, _, cadence_start) = state.State.set_channel_match_task(
+                channel_id, members_min, weekday, hour, cadence)
 
         # Let the user know what happened
         logger.info("Scheduled new match task in %s with min %s weekday %s hour %s and cadence %s",
                     channel_id, members_min, weekday, hour, cadence)
-        next_run = util.get_next_datetime(weekday, hour)
+        next_run = util.get_next_datetime_with_cadence(weekday, hour, datetime.now(), cadence, cadence_start)
 
         view = discord.ui.View(timeout=None)
         view.add_item(ScheduleButton())
 
         await interaction.response.send_message(
-            strings.scheduled_success(next_run),
+            strings.scheduled_success(next_run, cadence),
             ephemeral=True, silent=True, view=view)
 
     @app_commands.command(description="Cancel all scheduled matches in this channel")
@@ -307,8 +307,8 @@ class ScheduleButton(discord.ui.Button):
         msg += strings.scheduled_matches()
 
         if tasks:
-            for (day, hour, min) in tasks:
-                next_run = util.get_next_datetime(day, hour)
+            for (day, hour, min, cadence, cadence_start) in tasks:
+                next_run = util.get_next_datetime(day, hour, datetime.now(), cadence, cadence_start)
                 msg += strings.scheduled(next_run, min)
 
             await interaction.channel.send(msg)
diff --git a/matchy/cogs/strings.py b/matchy/cogs/strings.py
index 297e51b..a617194 100644
--- a/matchy/cogs/strings.py
+++ b/matchy/cogs/strings.py
@@ -85,11 +85,11 @@ def need_matcher_scope(): return [
 
 
 @randomised
-def scheduled_success(d): return [
-    f"Done :) Next run will be at {datetime_as_discord_time(d)}",
-    f"Woohoo! Scheduled for {datetime_as_discord_time(d)}",
-    f"Yessir, will do a matcho at {datetime_as_discord_time(d)}",
-    f"Arf Arf! Bork bork bark {datetime_as_discord_time(d)}",
+def scheduled_success(d, cadence): return [
+    f"Done :) Next run will be at {datetime_as_discord_time(d)} and every {cadence} week(s) after",
+    f"Woohoo! Scheduled for {datetime_as_discord_time(d)} plus each {cadence} week(s) after",
+    f"Yessir, will do a matcho every {cadence} week(s), first one is {datetime_as_discord_time(d)}",
+    f"Arf Arf! Bork bork bark {datetime_as_discord_time(d)} berk {cadence} week(s) arf",
 ]
 
 
diff --git a/matchy/state.py b/matchy/state.py
index fe24411..5af6096 100644
--- a/matchy/state.py
+++ b/matchy/state.py
@@ -358,7 +358,7 @@ class _State():
         )
         for tasks in all_tasks:
             for task in tasks:
-                yield (task[_Key.WEEKDAY], task[_Key.HOUR], task[_Key.MEMBERS_MIN])
+                yield _task_to_tuple(task)
 
     @safe_write
     def set_channel_match_task(self, channel_id: str, members_min: int, weekday: int, hour: int, cadence: int):
@@ -366,28 +366,27 @@ class _State():
         channel = self._tasks.setdefault(str(channel_id), {})
         matches = channel.setdefault(_Key.MATCH_TASKS, [])
 
-        found = False
-        for match in matches:
+        for match_task in matches:
             # Specifically check for the combination of weekday and hour
-            if match[_Key.WEEKDAY] == weekday and match[_Key.HOUR] == hour:
-                found = True
-                match[_Key.MEMBERS_MIN] = members_min
+            if match_task[_Key.WEEKDAY] == weekday and match_task[_Key.HOUR] == hour:
+                match_task[_Key.MEMBERS_MIN] = members_min
                 # If the cadence has changed, update it and reset the start
-                if cadence != match[_Key.CADENCE]:
-                    match[_Key.CADENCE] = cadence
-                    match[_Key.CADENCE_START] = datetime_to_ts(datetime.now())
-                # Return true as we've successfully changed the data in place
-                return True
+                if cadence != match_task[_Key.CADENCE]:
+                    match_task[_Key.CADENCE] = cadence
+                    match_task[_Key.CADENCE_START] = datetime_to_ts(datetime.now())
+                # Return as we've successfully changed the data in place
+                return _task_to_tuple(match_task)
 
         # If we didn't find it, add it to the schedule
-        if not found:
-            matches.append({
-                _Key.MEMBERS_MIN: members_min,
-                _Key.WEEKDAY: weekday,
-                _Key.HOUR: hour,
-                _Key.CADENCE: cadence,
-                _Key.CADENCE_START: datetime_to_ts(datetime.now())
-            })
+        match_task = {
+            _Key.MEMBERS_MIN: members_min,
+            _Key.WEEKDAY: weekday,
+            _Key.HOUR: hour,
+            _Key.CADENCE: cadence,
+            _Key.CADENCE_START: datetime_to_ts(datetime.now())
+        }
+        matches.append(match_task)
+        return _task_to_tuple(match_task)
 
     @safe_write
     def remove_channel_match_tasks(self, channel_id: str):
@@ -405,6 +404,14 @@ class _State():
         return self._dict[_Key.TASKS]
 
 
+def _task_to_tuple(task):
+    return (task[_Key.WEEKDAY],
+            task[_Key.HOUR],
+            task[_Key.MEMBERS_MIN],
+            task[_Key.CADENCE],
+            ts_to_datetime(task[_Key.CADENCE_START]))
+
+
 def load_from_file(file: str) -> _State:
     """
     Load the state from a files
diff --git a/matchy/util.py b/matchy/util.py
index 95274e3..b8fb71e 100644
--- a/matchy/util.py
+++ b/matchy/util.py
@@ -18,20 +18,32 @@ def format_list(list: list) -> str:
     return list[0] if list else ''
 
 
-def get_next_datetime(weekday, hour) -> datetime:
+def get_next_datetime(weekday: int, hour: int, start: datetime) -> datetime:
     """Get the next datetime for the given weekday and hour"""
-    now = datetime.now()
-    days_until_next_week = (weekday - now.weekday() + 7) % 7
+
+    days_until_next_week_run = (weekday - start.weekday() + 7) % 7
 
     # Account for when we're already beyond the time now
-    if days_until_next_week == 0 and now.hour >= hour:
-        days_until_next_week = 7
+    if days_until_next_week_run == 0 and start.hour >= hour:
+        days_until_next_week_run = 7
 
     # Calculate the next datetime
-    next_date = now + timedelta(days=days_until_next_week)
-    next_date = next_date.replace(hour=hour, minute=0, second=0, microsecond=0)
+    next_date = start + timedelta(days=days_until_next_week_run)
 
-    return next_date
+    return next_date.replace(hour=hour, minute=0, second=0, microsecond=0)
+
+
+def get_next_datetime_with_cadence(weekday: int, hour: int, start: datetime, cadence: int, cadence_start: datetime):
+    """Get the next datetime for given weekday, hour and cadence values"""
+
+    # Get the first run based on the cadence
+    next_time = get_next_datetime(weekday, hour, cadence_start)
+
+    # Walk forwards until we get the actual time
+    while next_time < start:
+        next_time += timedelta(weeks=cadence)
+
+    return next_time
 
 
 def datetime_as_discord_time(time: datetime) -> str:
diff --git a/tests/util_test.py b/tests/util_test.py
index 9bda465..b2971ed 100644
--- a/tests/util_test.py
+++ b/tests/util_test.py
@@ -1,4 +1,6 @@
 import matchy.util as util
+from datetime import datetime, timedelta
+import pytest
 
 
 def test_iterate_all_shifts():
@@ -50,3 +52,51 @@ def test_randomized():
 
     assert util.randomised(string)() == "foo"
     assert util.randomised(list)() in list()
+
+
+@pytest.mark.parametrize(
+    "weekday, hour, start, expected",
+    [
+        pytest.param(
+            0, 0, datetime(2024, 9, 22),
+            datetime(2024, 9, 23), id="tomorrow"
+        ),
+        pytest.param(
+            4, 16, datetime(2024, 9, 22),
+            datetime(2024, 9, 27, 16), id="complicated"
+        ),
+    ],
+)
+def test_get_next_datetime(weekday, hour, start, expected):
+    value = util.get_next_datetime(weekday, hour, start)
+    assert value == expected
+
+
+@pytest.mark.parametrize(
+    "weekday, hour, start, cadence, cadence_start, expected",
+    [
+        pytest.param(
+            0, 0, datetime(2024, 9, 22),
+            1, datetime(2024, 9, 22),
+            datetime(2024, 9, 23), id="tomorrow"
+        ),
+        pytest.param(
+            0, 0, datetime(2024, 9, 22),
+            2, datetime(2024, 9, 22),
+            datetime(2024, 9, 23), id="every-other"
+        ),
+        pytest.param(
+            0, 0, datetime(2024, 9, 22),
+            2, datetime(2024, 9, 14),
+            datetime(2024, 9, 30), id="every-other-before"
+        ),
+        pytest.param(
+            0, 0, datetime(2024, 9, 22),
+            3, datetime(2024, 9, 14),
+            datetime(2024, 10, 7), id="every-third"
+        ),
+    ],
+)
+def test_get_next_datetime_with_cadence(weekday, hour, start, expected, cadence, cadence_start):
+    value = util.get_next_datetime_with_cadence(weekday, hour, start, cadence, cadence_start)
+    assert value == expected