diff --git a/client/lib/generated/api/settings.pb.dart b/client/lib/generated/api/settings.pb.dart
index bce9280..3b0247b 100644
--- a/client/lib/generated/api/settings.pb.dart
+++ b/client/lib/generated/api/settings.pb.dart
@@ -793,6 +793,8 @@ class UpdateDiscordReminderSettingsRequest extends $pb.GeneratedMessage {
     $fixnum.Int64? discordEndReminderMins,
     $core.String? discordStartReminderMessage,
     $core.String? discordEndReminderMessage,
+    $core.bool? discordAutoDeleteStartReminder,
+    $core.bool? discordAutoDeleteEndReminder,
   }) {
     final result = create();
     if (discordStartReminderMins != null)
@@ -803,6 +805,10 @@ class UpdateDiscordReminderSettingsRequest extends $pb.GeneratedMessage {
       result.discordStartReminderMessage = discordStartReminderMessage;
     if (discordEndReminderMessage != null)
       result.discordEndReminderMessage = discordEndReminderMessage;
+    if (discordAutoDeleteStartReminder != null)
+      result.discordAutoDeleteStartReminder = discordAutoDeleteStartReminder;
+    if (discordAutoDeleteEndReminder != null)
+      result.discordAutoDeleteEndReminder = discordAutoDeleteEndReminder;
     return result;
   }
 
@@ -824,6 +830,8 @@ class UpdateDiscordReminderSettingsRequest extends $pb.GeneratedMessage {
     ..aInt64(2, _omitFieldNames ? '' : 'discordEndReminderMins')
     ..aOS(3, _omitFieldNames ? '' : 'discordStartReminderMessage')
     ..aOS(4, _omitFieldNames ? '' : 'discordEndReminderMessage')
+    ..aOB(5, _omitFieldNames ? '' : 'discordAutoDeleteStartReminder')
+    ..aOB(6, _omitFieldNames ? '' : 'discordAutoDeleteEndReminder')
     ..hasRequiredFields = false;
 
   @$core.Deprecated('See https://github.com/google/protobuf.dart/issues/998.')
@@ -884,6 +892,24 @@ class UpdateDiscordReminderSettingsRequest extends $pb.GeneratedMessage {
   $core.bool hasDiscordEndReminderMessage() => $_has(3);
   @$pb.TagNumber(4)
   void clearDiscordEndReminderMessage() => $_clearField(4);
+
+  @$pb.TagNumber(5)
+  $core.bool get discordAutoDeleteStartReminder => $_getBF(4);
+  @$pb.TagNumber(5)
+  set discordAutoDeleteStartReminder($core.bool value) => $_setBool(4, value);
+  @$pb.TagNumber(5)
+  $core.bool hasDiscordAutoDeleteStartReminder() => $_has(4);
+  @$pb.TagNumber(5)
+  void clearDiscordAutoDeleteStartReminder() => $_clearField(5);
+
+  @$pb.TagNumber(6)
+  $core.bool get discordAutoDeleteEndReminder => $_getBF(5);
+  @$pb.TagNumber(6)
+  set discordAutoDeleteEndReminder($core.bool value) => $_setBool(5, value);
+  @$pb.TagNumber(6)
+  $core.bool hasDiscordAutoDeleteEndReminder() => $_has(5);
+  @$pb.TagNumber(6)
+  void clearDiscordAutoDeleteEndReminder() => $_clearField(6);
 }
 
 class UpdateDiscordReminderSettingsResponse extends $pb.GeneratedMessage {
diff --git a/client/lib/generated/api/settings.pbjson.dart b/client/lib/generated/api/settings.pbjson.dart
index 5899cc2..92f6389 100644
--- a/client/lib/generated/api/settings.pbjson.dart
+++ b/client/lib/generated/api/settings.pbjson.dart
@@ -340,12 +340,32 @@ const UpdateDiscordReminderSettingsRequest$json = {
       '10': 'discordEndReminderMessage',
       '17': true
     },
+    {
+      '1': 'discord_auto_delete_start_reminder',
+      '3': 5,
+      '4': 1,
+      '5': 8,
+      '9': 4,
+      '10': 'discordAutoDeleteStartReminder',
+      '17': true
+    },
+    {
+      '1': 'discord_auto_delete_end_reminder',
+      '3': 6,
+      '4': 1,
+      '5': 8,
+      '9': 5,
+      '10': 'discordAutoDeleteEndReminder',
+      '17': true
+    },
   ],
   '8': [
     {'1': '_discord_start_reminder_mins'},
     {'1': '_discord_end_reminder_mins'},
     {'1': '_discord_start_reminder_message'},
     {'1': '_discord_end_reminder_message'},
+    {'1': '_discord_auto_delete_start_reminder'},
+    {'1': '_discord_auto_delete_end_reminder'},
   ],
 };
 
@@ -356,9 +376,14 @@ final $typed_data.Uint8List updateDiscordReminderSettingsRequestDescriptor = $co
     'aXNjb3JkX2VuZF9yZW1pbmRlcl9taW5zGAIgASgDSAFSFmRpc2NvcmRFbmRSZW1pbmRlck1pbn'
     'OIAQESSAoeZGlzY29yZF9zdGFydF9yZW1pbmRlcl9tZXNzYWdlGAMgASgJSAJSG2Rpc2NvcmRT'
     'dGFydFJlbWluZGVyTWVzc2FnZYgBARJEChxkaXNjb3JkX2VuZF9yZW1pbmRlcl9tZXNzYWdlGA'
-    'QgASgJSANSGWRpc2NvcmRFbmRSZW1pbmRlck1lc3NhZ2WIAQFCHgocX2Rpc2NvcmRfc3RhcnRf'
-    'cmVtaW5kZXJfbWluc0IcChpfZGlzY29yZF9lbmRfcmVtaW5kZXJfbWluc0IhCh9fZGlzY29yZF'
-    '9zdGFydF9yZW1pbmRlcl9tZXNzYWdlQh8KHV9kaXNjb3JkX2VuZF9yZW1pbmRlcl9tZXNzYWdl');
+    'QgASgJSANSGWRpc2NvcmRFbmRSZW1pbmRlck1lc3NhZ2WIAQESTwoiZGlzY29yZF9hdXRvX2Rl'
+    'bGV0ZV9zdGFydF9yZW1pbmRlchgFIAEoCEgEUh5kaXNjb3JkQXV0b0RlbGV0ZVN0YXJ0UmVtaW'
+    '5kZXKIAQESSwogZGlzY29yZF9hdXRvX2RlbGV0ZV9lbmRfcmVtaW5kZXIYBiABKAhIBVIcZGlz'
+    'Y29yZEF1dG9EZWxldGVFbmRSZW1pbmRlcogBAUIeChxfZGlzY29yZF9zdGFydF9yZW1pbmRlcl'
+    '9taW5zQhwKGl9kaXNjb3JkX2VuZF9yZW1pbmRlcl9taW5zQiEKH19kaXNjb3JkX3N0YXJ0X3Jl'
+    'bWluZGVyX21lc3NhZ2VCHwodX2Rpc2NvcmRfZW5kX3JlbWluZGVyX21lc3NhZ2VCJQojX2Rpc2'
+    'NvcmRfYXV0b19kZWxldGVfc3RhcnRfcmVtaW5kZXJCIwohX2Rpc2NvcmRfYXV0b19kZWxldGVf'
+    'ZW5kX3JlbWluZGVy');
 
 @$core.Deprecated('Use updateDiscordReminderSettingsResponseDescriptor instead')
 const UpdateDiscordReminderSettingsResponse$json = {
diff --git a/client/lib/generated/db/db.pb.dart b/client/lib/generated/db/db.pb.dart
index e3902f8..ddd7119 100644
--- a/client/lib/generated/db/db.pb.dart
+++ b/client/lib/generated/db/db.pb.dart
@@ -579,12 +579,14 @@ class Notification extends $pb.GeneratedMessage {
     $core.String? sessionId,
     $core.String? teamMemberId,
     $core.bool? sent,
+    $core.String? discordMessageId,
   }) {
     final result = create();
     if (notificationType != null) result.notificationType = notificationType;
     if (sessionId != null) result.sessionId = sessionId;
     if (teamMemberId != null) result.teamMemberId = teamMemberId;
     if (sent != null) result.sent = sent;
+    if (discordMessageId != null) result.discordMessageId = discordMessageId;
     return result;
   }
 
@@ -606,6 +608,7 @@ class Notification extends $pb.GeneratedMessage {
     ..aOS(2, _omitFieldNames ? '' : 'sessionId')
     ..aOS(3, _omitFieldNames ? '' : 'teamMemberId')
     ..aOB(4, _omitFieldNames ? '' : 'sent')
+    ..aOS(5, _omitFieldNames ? '' : 'discordMessageId')
     ..hasRequiredFields = false;
 
   @$core.Deprecated('See https://github.com/google/protobuf.dart/issues/998.')
@@ -662,6 +665,15 @@ class Notification extends $pb.GeneratedMessage {
   $core.bool hasSent() => $_has(3);
   @$pb.TagNumber(4)
   void clearSent() => $_clearField(4);
+
+  @$pb.TagNumber(5)
+  $core.String get discordMessageId => $_getSZ(4);
+  @$pb.TagNumber(5)
+  set discordMessageId($core.String value) => $_setString(4, value);
+  @$pb.TagNumber(5)
+  $core.bool hasDiscordMessageId() => $_has(4);
+  @$pb.TagNumber(5)
+  void clearDiscordMessageId() => $_clearField(5);
 }
 
 class Logo extends $pb.GeneratedMessage {
@@ -889,6 +901,8 @@ class Settings extends $pb.GeneratedMessage {
     $core.Iterable<TeamMemberType>? leaderboardMemberTypes,
     $core.bool? discordRsvpReactionsEnabled,
     $core.String? discordNotificationChannelId,
+    $core.bool? discordAutoDeleteStartReminder,
+    $core.bool? discordAutoDeleteEndReminder,
   }) {
     final result = create();
     if (nextSessionThresholdSecs != null)
@@ -933,6 +947,10 @@ class Settings extends $pb.GeneratedMessage {
       result.discordRsvpReactionsEnabled = discordRsvpReactionsEnabled;
     if (discordNotificationChannelId != null)
       result.discordNotificationChannelId = discordNotificationChannelId;
+    if (discordAutoDeleteStartReminder != null)
+      result.discordAutoDeleteStartReminder = discordAutoDeleteStartReminder;
+    if (discordAutoDeleteEndReminder != null)
+      result.discordAutoDeleteEndReminder = discordAutoDeleteEndReminder;
     return result;
   }
 
@@ -977,6 +995,8 @@ class Settings extends $pb.GeneratedMessage {
         defaultEnumValue: TeamMemberType.STUDENT)
     ..aOB(23, _omitFieldNames ? '' : 'discordRsvpReactionsEnabled')
     ..aOS(24, _omitFieldNames ? '' : 'discordNotificationChannelId')
+    ..aOB(25, _omitFieldNames ? '' : 'discordAutoDeleteStartReminder')
+    ..aOB(26, _omitFieldNames ? '' : 'discordAutoDeleteEndReminder')
     ..hasRequiredFields = false;
 
   @$core.Deprecated('See https://github.com/google/protobuf.dart/issues/998.')
@@ -1208,6 +1228,24 @@ class Settings extends $pb.GeneratedMessage {
   $core.bool hasDiscordNotificationChannelId() => $_has(23);
   @$pb.TagNumber(24)
   void clearDiscordNotificationChannelId() => $_clearField(24);
+
+  @$pb.TagNumber(25)
+  $core.bool get discordAutoDeleteStartReminder => $_getBF(24);
+  @$pb.TagNumber(25)
+  set discordAutoDeleteStartReminder($core.bool value) => $_setBool(24, value);
+  @$pb.TagNumber(25)
+  $core.bool hasDiscordAutoDeleteStartReminder() => $_has(24);
+  @$pb.TagNumber(25)
+  void clearDiscordAutoDeleteStartReminder() => $_clearField(25);
+
+  @$pb.TagNumber(26)
+  $core.bool get discordAutoDeleteEndReminder => $_getBF(25);
+  @$pb.TagNumber(26)
+  set discordAutoDeleteEndReminder($core.bool value) => $_setBool(25, value);
+  @$pb.TagNumber(26)
+  $core.bool hasDiscordAutoDeleteEndReminder() => $_has(25);
+  @$pb.TagNumber(26)
+  void clearDiscordAutoDeleteEndReminder() => $_clearField(26);
 }
 
 const $core.bool _omitFieldNames =
diff --git a/client/lib/generated/db/db.pbjson.dart b/client/lib/generated/db/db.pbjson.dart
index 4af19cd..3b0dc18 100644
--- a/client/lib/generated/db/db.pbjson.dart
+++ b/client/lib/generated/db/db.pbjson.dart
@@ -268,9 +268,19 @@ const Notification$json = {
       '17': true
     },
     {'1': 'sent', '3': 4, '4': 1, '5': 8, '10': 'sent'},
+    {
+      '1': 'discord_message_id',
+      '3': 5,
+      '4': 1,
+      '5': 9,
+      '9': 1,
+      '10': 'discordMessageId',
+      '17': true
+    },
   ],
   '8': [
     {'1': '_team_member_id'},
+    {'1': '_discord_message_id'},
   ],
 };
 
@@ -279,7 +289,8 @@ final $typed_data.Uint8List notificationDescriptor = $convert.base64Decode(
     'CgxOb3RpZmljYXRpb24SRAoRbm90aWZpY2F0aW9uX3R5cGUYASABKA4yFy50ay5kYi5Ob3RpZm'
     'ljYXRpb25UeXBlUhBub3RpZmljYXRpb25UeXBlEh0KCnNlc3Npb25faWQYAiABKAlSCXNlc3Np'
     'b25JZBIpCg50ZWFtX21lbWJlcl9pZBgDIAEoCUgAUgx0ZWFtTWVtYmVySWSIAQESEgoEc2VudB'
-    'gEIAEoCFIEc2VudEIRCg9fdGVhbV9tZW1iZXJfaWQ=');
+    'gEIAEoCFIEc2VudBIxChJkaXNjb3JkX21lc3NhZ2VfaWQYBSABKAlIAVIQZGlzY29yZE1lc3Nh'
+    'Z2VJZIgBAUIRCg9fdGVhbV9tZW1iZXJfaWRCFQoTX2Rpc2NvcmRfbWVzc2FnZV9pZA==');
 
 @$core.Deprecated('Use logoDescriptor instead')
 const Logo$json = {
@@ -473,6 +484,20 @@ const Settings$json = {
       '5': 8,
       '10': 'discordRsvpReactionsEnabled'
     },
+    {
+      '1': 'discord_auto_delete_start_reminder',
+      '3': 25,
+      '4': 1,
+      '5': 8,
+      '10': 'discordAutoDeleteStartReminder'
+    },
+    {
+      '1': 'discord_auto_delete_end_reminder',
+      '3': 26,
+      '4': 1,
+      '5': 8,
+      '10': 'discordAutoDeleteEndReminder'
+    },
   ],
 };
 
@@ -503,4 +528,7 @@ final $typed_data.Uint8List settingsDescriptor = $convert.base64Decode(
     'ZF9zaG93X292ZXJ0aW1lGBUgASgIUhdsZWFkZXJib2FyZFNob3dPdmVydGltZRJPChhsZWFkZX'
     'Jib2FyZF9tZW1iZXJfdHlwZXMYFiADKA4yFS50ay5kYi5UZWFtTWVtYmVyVHlwZVIWbGVhZGVy'
     'Ym9hcmRNZW1iZXJUeXBlcxJDCh5kaXNjb3JkX3JzdnBfcmVhY3Rpb25zX2VuYWJsZWQYFyABKA'
-    'hSG2Rpc2NvcmRSc3ZwUmVhY3Rpb25zRW5hYmxlZA==');
+    'hSG2Rpc2NvcmRSc3ZwUmVhY3Rpb25zRW5hYmxlZBJKCiJkaXNjb3JkX2F1dG9fZGVsZXRlX3N0'
+    'YXJ0X3JlbWluZGVyGBkgASgIUh5kaXNjb3JkQXV0b0RlbGV0ZVN0YXJ0UmVtaW5kZXISRgogZG'
+    'lzY29yZF9hdXRvX2RlbGV0ZV9lbmRfcmVtaW5kZXIYGiABKAhSHGRpc2NvcmRBdXRvRGVsZXRl'
+    'RW5kUmVtaW5kZXI=');
diff --git a/client/lib/views/setup/integrations_setup.dart b/client/lib/views/setup/integrations_setup.dart
index f34a0f6..b22b3d8 100644
--- a/client/lib/views/setup/integrations_setup.dart
+++ b/client/lib/views/setup/integrations_setup.dart
@@ -27,6 +27,8 @@ class IntegrationsSetupTab extends HookConsumerWidget {
     final endReminderMinsController = useTextEditingController();
     final startReminderMessageController = useTextEditingController();
     final endReminderMessageController = useTextEditingController();
+    final autoDeleteStartReminder = useState(false);
+    final autoDeleteEndReminder = useState(false);
     final rsvpReactionsEnabled = useState(true);
     final selfLinkEnabled = useState(false);
     final nameSyncEnabled = useState(true);
@@ -67,6 +69,8 @@ class IntegrationsSetupTab extends HookConsumerWidget {
               : '15';
           startReminderMessageController.text = s.discordStartReminderMessage;
           endReminderMessageController.text = s.discordEndReminderMessage;
+          autoDeleteStartReminder.value = s.discordAutoDeleteStartReminder;
+          autoDeleteEndReminder.value = s.discordAutoDeleteEndReminder;
           rsvpReactionsEnabled.value = s.discordRsvpReactionsEnabled;
           selfLinkEnabled.value = s.discordSelfLinkEnabled;
           nameSyncEnabled.value = s.discordNameSyncEnabled;
@@ -123,6 +127,9 @@ class IntegrationsSetupTab extends HookConsumerWidget {
                 discordStartReminderMessage:
                     startReminderMessageController.text,
                 discordEndReminderMessage: endReminderMessageController.text,
+                discordAutoDeleteStartReminder:
+                    autoDeleteStartReminder.value,
+                discordAutoDeleteEndReminder: autoDeleteEndReminder.value,
               ),
             ),
       );
@@ -312,6 +319,25 @@ class IntegrationsSetupTab extends HookConsumerWidget {
           onUpdate: updateDiscordReminder,
         ),
         const SizedBox(height: 24),
+        SettingRow(
+          label: 'Auto Delete Start Reminders',
+          description:
+              'Automatically delete the start reminder message from Discord once the session start time has passed.',
+          child: Row(
+            children: [
+              Switch(
+                value: autoDeleteStartReminder.value,
+                onChanged: (value) {
+                  autoDeleteStartReminder.value = value;
+                  updateDiscordReminder();
+                },
+              ),
+              const SizedBox(width: 8),
+              Text(autoDeleteStartReminder.value ? 'Enabled' : 'Disabled'),
+            ],
+          ),
+        ),
+        const SizedBox(height: 24),
         SettingRow(
           label: 'Start Reminder RSVP Reactions',
           description:
@@ -354,6 +380,25 @@ class IntegrationsSetupTab extends HookConsumerWidget {
           onUpdate: updateDiscordReminder,
         ),
         const SizedBox(height: 24),
+        SettingRow(
+          label: 'Auto Delete End Reminders',
+          description:
+              'Automatically delete the end reminder message from Discord once the session end time has passed.',
+          child: Row(
+            children: [
+              Switch(
+                value: autoDeleteEndReminder.value,
+                onChanged: (value) {
+                  autoDeleteEndReminder.value = value;
+                  updateDiscordReminder();
+                },
+              ),
+              const SizedBox(width: 8),
+              Text(autoDeleteEndReminder.value ? 'Enabled' : 'Disabled'),
+            ],
+          ),
+        ),
+        const SizedBox(height: 24),
         SettingRow(
           label: 'Self-Linking',
           description:
diff --git a/protos/api/settings.proto b/protos/api/settings.proto
index a7cb0c3..5ef919b 100644
--- a/protos/api/settings.proto
+++ b/protos/api/settings.proto
@@ -98,6 +98,8 @@ message UpdateDiscordReminderSettingsRequest {
   optional int64 discord_end_reminder_mins = 2;
   optional string discord_start_reminder_message = 3;
   optional string discord_end_reminder_message = 4;
+  optional bool discord_auto_delete_start_reminder = 5;
+  optional bool discord_auto_delete_end_reminder = 6;
 }
 
 message UpdateDiscordReminderSettingsResponse {}
diff --git a/protos/db/db.proto b/protos/db/db.proto
index b09a6c0..4a6d46f 100644
--- a/protos/db/db.proto
+++ b/protos/db/db.proto
@@ -63,6 +63,7 @@ message Notification {
   string session_id = 2;
   optional string team_member_id = 3;
   bool sent = 4;
+  optional string discord_message_id = 5;
 }
 
 message Logo {
@@ -110,4 +111,6 @@ message Settings {
   bool leaderboard_show_overtime = 21;
   repeated TeamMemberType leaderboard_member_types = 22;
   bool discord_rsvp_reactions_enabled = 23;
+  bool discord_auto_delete_start_reminder = 25;
+  bool discord_auto_delete_end_reminder = 26;
 }
diff --git a/server/src/generated/tk.api.rs b/server/src/generated/tk.api.rs
index c234d24..dec379c 100644
--- a/server/src/generated/tk.api.rs
+++ b/server/src/generated/tk.api.rs
@@ -3258,6 +3258,10 @@ pub struct UpdateDiscordReminderSettingsRequest {
     pub discord_end_reminder_message: ::core::option::Option<
         ::prost::alloc::string::String,
     >,
+    #[prost(bool, optional, tag = "5")]
+    pub discord_auto_delete_start_reminder: ::core::option::Option<bool>,
+    #[prost(bool, optional, tag = "6")]
+    pub discord_auto_delete_end_reminder: ::core::option::Option<bool>,
 }
 #[derive(Clone, Copy, PartialEq, Eq, Hash, ::prost::Message)]
 pub struct UpdateDiscordReminderSettingsResponse {}
diff --git a/server/src/generated/tk.db.rs b/server/src/generated/tk.db.rs
index 0674472..5441358 100644
--- a/server/src/generated/tk.db.rs
+++ b/server/src/generated/tk.db.rs
@@ -72,6 +72,8 @@ pub struct Notification {
     pub team_member_id: ::core::option::Option<::prost::alloc::string::String>,
     #[prost(bool, tag = "4")]
     pub sent: bool,
+    #[prost(string, optional, tag = "5")]
+    pub discord_message_id: ::core::option::Option<::prost::alloc::string::String>,
 }
 #[derive(Clone, PartialEq, Eq, Hash, ::prost::Message)]
 pub struct Logo {
@@ -144,6 +146,10 @@ pub struct Settings {
     pub leaderboard_member_types: ::prost::alloc::vec::Vec<i32>,
     #[prost(bool, tag = "23")]
     pub discord_rsvp_reactions_enabled: bool,
+    #[prost(bool, tag = "25")]
+    pub discord_auto_delete_start_reminder: bool,
+    #[prost(bool, tag = "26")]
+    pub discord_auto_delete_end_reminder: bool,
 }
 #[derive(Clone, Copy, Debug, PartialEq, Eq, Hash, PartialOrd, Ord, ::prost::Enumeration)]
 #[repr(i32)]
diff --git a/server/src/modules/discord/service.rs b/server/src/modules/discord/service.rs
index ce414f2..9284e1a 100644
--- a/server/src/modules/discord/service.rs
+++ b/server/src/modules/discord/service.rs
@@ -126,83 +126,142 @@ impl ScheduledService for DiscordNotificationService {
 
     // --- Session Start/End Reminders ---
     for (id, session) in &sessions {
-      if session.finished {
-        continue;
-      }
-
       let start_secs = session.start_time.as_ref().map_or(0, |t| t.seconds);
       let end_secs = session.end_time.as_ref().map_or(0, |t| t.seconds);
-      let location = locations.get(&session.location_id).map_or("Unknown", |l| l.location.as_str());
-
-      // Session starting soon reminder
-      if start_reminder_secs > 0 {
-        let time_until_start = start_secs - now_secs;
-        if time_until_start > 0
-          && time_until_start <= start_reminder_secs
-          && !Notification::exists(NotificationType::SessionStartReminder, id, None)?
-        {
-          let mins = time_until_start / 60;
-          let msg = DiscordNotificationService::replace_placeholders(
-            start_msg_template,
-            location,
-            start_secs,
-            end_secs,
-            tz,
-            Some(mins),
-          );
-
-          match block_on(async { announcement_channel.say(&http, &msg).await }) {
-            Ok(sent_msg) => {
-              if settings.discord_rsvp_reactions_enabled {
-                let _ = block_on(async { sent_msg.react(&http, ReactionType::Unicode("👍".to_string())).await });
-                let _ = block_on(async { sent_msg.react(&http, ReactionType::Unicode("👎".to_string())).await });
-
-                if let Err(e) = SessionRsvpMessage::set(&sent_msg.id.to_string(), id) {
-                  log::error!("[DiscordNotificationService] Failed to store RSVP message mapping: {e}");
+
+      // Send reminders only for sessions that haven't finished
+      if !session.finished {
+        let location = locations.get(&session.location_id).map_or("Unknown", |l| l.location.as_str());
+
+        // Session starting soon reminder
+        if start_reminder_secs > 0 {
+          let time_until_start = start_secs - now_secs;
+          if time_until_start > 0
+            && time_until_start <= start_reminder_secs
+            && !Notification::exists(NotificationType::SessionStartReminder, id, None)?
+          {
+            let mins = time_until_start / 60;
+            let msg = DiscordNotificationService::replace_placeholders(
+              start_msg_template,
+              location,
+              start_secs,
+              end_secs,
+              tz,
+              Some(mins),
+            );
+
+            match block_on(async { announcement_channel.say(&http, &msg).await }) {
+              Ok(sent_msg) => {
+                let discord_message_id = sent_msg.id.to_string();
+
+                if settings.discord_rsvp_reactions_enabled {
+                  let _ = block_on(async { sent_msg.react(&http, ReactionType::Unicode("👍".to_string())).await });
+                  let _ = block_on(async { sent_msg.react(&http, ReactionType::Unicode("👎".to_string())).await });
+
+                  if let Err(e) = SessionRsvpMessage::set(&discord_message_id, id) {
+                    log::error!("[DiscordNotificationService] Failed to store RSVP message mapping: {e}");
+                  }
                 }
-              }
 
-              Notification::add(&Notification {
-                notification_type: NotificationType::SessionStartReminder as i32,
-                session_id: id.clone(),
-                team_member_id: None,
-                sent: true,
-              })?;
+                Notification::add(&Notification {
+                  notification_type: NotificationType::SessionStartReminder as i32,
+                  session_id: id.clone(),
+                  team_member_id: None,
+                  sent: true,
+                  discord_message_id: Some(discord_message_id),
+                })?;
+              }
+              Err(e) => {
+                log::error!("[DiscordNotificationService] Failed to send start reminder: {e}");
+              }
             }
-            Err(e) => {
-              log::error!("[DiscordNotificationService] Failed to send start reminder: {e}");
+          }
+        }
+
+        // Session ending soon reminder
+        if end_reminder_secs > 0 {
+          let time_until_end = end_secs - now_secs;
+          if time_until_end > 0
+            && time_until_end <= end_reminder_secs
+            && now_secs >= start_secs
+            && !Notification::exists(NotificationType::SessionEndReminder, id, None)?
+          {
+            let mins = time_until_end / 60;
+            let msg = DiscordNotificationService::replace_placeholders(
+              end_msg_template,
+              location,
+              start_secs,
+              end_secs,
+              tz,
+              Some(mins),
+            );
+
+            match block_on(async { announcement_channel.say(&http, &msg).await }) {
+              Ok(sent_msg) => {
+                Notification::add(&Notification {
+                  notification_type: NotificationType::SessionEndReminder as i32,
+                  session_id: id.clone(),
+                  team_member_id: None,
+                  sent: true,
+                  discord_message_id: Some(sent_msg.id.to_string()),
+                })?;
+              }
+              Err(e) => {
+                log::error!("[DiscordNotificationService] Failed to send end reminder: {e}");
+              }
             }
           }
         }
       }
 
-      // Session ending soon reminder
-      if end_reminder_secs > 0 {
-        let time_until_end = end_secs - now_secs;
-        if time_until_end > 0
-          && time_until_end <= end_reminder_secs
-          && now_secs >= start_secs
-          && !Notification::exists(NotificationType::SessionEndReminder, id, None)?
-        {
-          let mins = time_until_end / 60;
-          let msg = DiscordNotificationService::replace_placeholders(
-            end_msg_template,
-            location,
-            start_secs,
-            end_secs,
-            tz,
-            Some(mins),
-          );
-
-          if let Err(e) = block_on(async { announcement_channel.say(&http, &msg).await }) {
-            log::error!("[DiscordNotificationService] Failed to send end reminder: {e}");
-          } else {
-            Notification::add(&Notification {
-              notification_type: NotificationType::SessionEndReminder as i32,
-              session_id: id.clone(),
-              team_member_id: None,
-              sent: true,
-            })?;
+      // Auto-delete start reminder when session has started (time-based, independent of finished state)
+      if settings.discord_auto_delete_start_reminder && start_secs > 0 && now_secs >= start_secs {
+        let session_notifs = Notification::get_by_session_id(id)?;
+        if let Some((notif_id, notif)) = session_notifs.into_iter().find(|(_, n)| {
+          n.notification_type == NotificationType::SessionStartReminder as i32 && n.discord_message_id.is_some()
+        }) {
+          let discord_msg_id = notif.discord_message_id.as_ref().unwrap();
+          let msg_id: u64 = discord_msg_id.parse().unwrap_or(0);
+          if msg_id > 0
+            && let Err(e) = block_on(async {
+              announcement_channel
+                .delete_message(&http, serenity::model::id::MessageId::new(msg_id))
+                .await
+            })
+          {
+            log::warn!("[DiscordNotificationService] Failed to delete start reminder message {discord_msg_id}: {e}");
+          }
+          // Clear the message ID so we don't attempt deletion again
+          let mut updated = notif.clone();
+          updated.discord_message_id = None;
+          if let Err(e) = Notification::update(&notif_id, &updated) {
+            log::error!("[DiscordNotificationService] Failed to clear start reminder message ID: {e}");
+          }
+        }
+      }
+
+      // Auto-delete end reminder when session has ended (time-based, independent of finished state)
+      if settings.discord_auto_delete_end_reminder && end_secs > 0 && now_secs >= end_secs {
+        let session_notifs = Notification::get_by_session_id(id)?;
+        if let Some((notif_id, notif)) = session_notifs.into_iter().find(|(_, n)| {
+          n.notification_type == NotificationType::SessionEndReminder as i32 && n.discord_message_id.is_some()
+        }) {
+          let discord_msg_id = notif.discord_message_id.as_ref().unwrap();
+          let msg_id: u64 = discord_msg_id.parse().unwrap_or(0);
+          if msg_id > 0
+            && let Err(e) = block_on(async {
+              announcement_channel
+                .delete_message(&http, serenity::model::id::MessageId::new(msg_id))
+                .await
+            })
+          {
+            log::warn!("[DiscordNotificationService] Failed to delete end reminder message {discord_msg_id}: {e}");
+          }
+          // Clear the message ID so we don't attempt deletion again
+          let mut updated = notif.clone();
+          updated.discord_message_id = None;
+          if let Err(e) = Notification::update(&notif_id, &updated) {
+            log::error!("[DiscordNotificationService] Failed to clear end reminder message ID: {e}");
           }
         }
       }
@@ -271,6 +330,7 @@ impl ScheduledService for DiscordNotificationService {
                 session_id: pes.session_id.clone(),
                 team_member_id: Some(ms.team_member_id.clone()),
                 sent: true,
+                discord_message_id: None,
               })
             {
               log::error!(
diff --git a/server/src/modules/notification/api.rs b/server/src/modules/notification/api.rs
index 6348c23..ab532be 100644
--- a/server/src/modules/notification/api.rs
+++ b/server/src/modules/notification/api.rs
@@ -108,6 +108,7 @@ impl NotificationService for NotificationApi {
       session_id: req.session_id,
       team_member_id: req.team_member_id,
       sent: req.sent,
+      discord_message_id: None,
     };
     Notification::add(&notification).map_err(|e| Status::internal(format!("Failed to create notification: {e}")))?;
 
@@ -137,6 +138,7 @@ impl NotificationService for NotificationApi {
       session_id: req.session_id,
       team_member_id: req.team_member_id,
       sent: req.sent,
+      discord_message_id: None,
     };
     Notification::update(&req.id, &notification)
       .map_err(|e| Status::internal(format!("Failed to update notification: {e}")))?;
diff --git a/server/src/modules/session/service.rs b/server/src/modules/session/service.rs
index c318f4e..6090092 100644
--- a/server/src/modules/session/service.rs
+++ b/server/src/modules/session/service.rs
@@ -58,6 +58,7 @@ impl ScheduledService for SessionService {
             session_id: pes.session_id.clone(),
             team_member_id: Some(ms.team_member_id.clone()),
             sent: false,
+            discord_message_id: None,
           };
           if let Err(e) = Notification::add(&notification) {
             log::error!(
diff --git a/server/src/modules/settings/api.rs b/server/src/modules/settings/api.rs
index d5e2d55..369a2f9 100644
--- a/server/src/modules/settings/api.rs
+++ b/server/src/modules/settings/api.rs
@@ -190,6 +190,14 @@ impl SettingsService for SettingsApi {
       settings.discord_end_reminder_message = v;
     }
 
+    if let Some(v) = req.discord_auto_delete_start_reminder {
+      settings.discord_auto_delete_start_reminder = v;
+    }
+
+    if let Some(v) = req.discord_auto_delete_end_reminder {
+      settings.discord_auto_delete_end_reminder = v;
+    }
+
     Self::save_settings(&settings)?;
     Ok(Response::new(UpdateDiscordReminderSettingsResponse {}))
   }
diff --git a/server/src/modules/settings/repository.rs b/server/src/modules/settings/repository.rs
index 5d16c87..c7310ff 100644
--- a/server/src/modules/settings/repository.rs
+++ b/server/src/modules/settings/repository.rs
@@ -83,6 +83,8 @@ impl SettingsRepository for Settings {
       leaderboard_show_overtime: true,
       leaderboard_member_types: vec![TeamMemberType::Student as i32, TeamMemberType::Mentor as i32],
       discord_rsvp_reactions_enabled: true,
+      discord_auto_delete_start_reminder: false,
+      discord_auto_delete_end_reminder: false,
     };
 
     if let Some(s) = table.get::<Settings>(SETTINGS_KEY)? {