diff --git a/Content.Server/GameTicking/GameTicker.CVars.cs b/Content.Server/GameTicking/GameTicker.CVars.cs
index 8bb7f83856..beae71c50b 100644
--- a/Content.Server/GameTicking/GameTicker.CVars.cs
+++ b/Content.Server/GameTicking/GameTicker.CVars.cs
@@ -31,7 +31,7 @@ namespace Content.Server.GameTicking
         public string? ServerName { get; private set; }
 
         [ViewVariables]
-        private long? DiscordRoundEndRole { get; set; }
+        private string? DiscordRoundEndRole { get; set; }
 
         private WebhookIdentifier? _webhookIdentifier;
 
@@ -65,7 +65,7 @@ namespace Content.Server.GameTicking
                 // TODO why tf is the server name on admin logs
                 ServerName = value;
             }, true);
-            _configurationManager.OnValueChanged(CCVars.DiscordRoundRestartWebhook, value =>
+            _configurationManager.OnValueChanged(CCVars.DiscordRoundUpdateWebhook, value =>
             {
                 if (!string.IsNullOrWhiteSpace(value))
                 {
@@ -76,7 +76,7 @@ namespace Content.Server.GameTicking
             {
                 DiscordRoundEndRole = value;
 
-                if (value == 0)
+                if (value == string.Empty)
                 {
                     DiscordRoundEndRole = null;
                 }
diff --git a/Content.Server/GameTicking/GameTicker.RoundFlow.cs b/Content.Server/GameTicking/GameTicker.RoundFlow.cs
index a20cefb233..aa66ee9372 100644
--- a/Content.Server/GameTicking/GameTicker.RoundFlow.cs
+++ b/Content.Server/GameTicking/GameTicker.RoundFlow.cs
@@ -252,6 +252,7 @@ namespace Content.Server.GameTicking
             UpdateLateJoinStatus();
             AnnounceRound();
             UpdateInfoText();
+            SendRoundStartedDiscordMessage();
 
 #if EXCEPTION_TOLERANCE
             }
@@ -395,16 +396,21 @@ namespace Content.Server.GameTicking
                 if (_webhookIdentifier == null)
                     return;
 
-                var content = "The round has ended.";
-                if (DiscordRoundEndRole != null)
-                    content += $"\n\n<@&{DiscordRoundEndRole}>, the server will reboot shortly!";
+                var duration = RoundDuration();
+                var content = Loc.GetString("discord-round-notifications-end",
+                    ("id", RoundId),
+                    ("hours", Math.Truncate(duration.TotalHours)),
+                    ("minutes", duration.Minutes),
+                    ("seconds", duration.Seconds));
+                var payload = new WebhookPayload { Content = content };
 
-                var payload = new WebhookPayload
-                {
-                    Content = content,
-                    Username = ServerName,
-                };
+                await _discord.CreateMessage(_webhookIdentifier.Value, payload);
 
+                if (DiscordRoundEndRole == null)
+                    return;
+
+                content = Loc.GetString("discord-round-notifications-end-ping", ("roleId", DiscordRoundEndRole));
+                payload = new WebhookPayload { Content = content };
                 payload.AllowedMentions.AllowRoleMentions();
 
                 await _discord.CreateMessage(_webhookIdentifier.Value, payload);
@@ -439,6 +445,7 @@ namespace Content.Server.GameTicking
             RandomizeLobbyBackground();
             ResettingCleanup();
             IncrementRoundNumber();
+            SendRoundStartingDiscordMessage();
 
             if (!LobbyEnabled)
             {
@@ -456,8 +463,6 @@ namespace Content.Server.GameTicking
 
                 ReqWindowAttentionAll();
             }
-
-            SendRoundStartingDiscordMessage();
         }
 
         private async void SendRoundStartingDiscordMessage()
@@ -467,13 +472,9 @@ namespace Content.Server.GameTicking
                 if (_webhookIdentifier == null)
                     return;
 
-                var content = "New round starting!";
+                var content = Loc.GetString("discord-round-notifications-new");
 
-                var payload = new WebhookPayload
-                {
-                    Content = content,
-                    Username = ServerName,
-                };
+                var payload = new WebhookPayload { Content = content };
 
                 await _discord.CreateMessage(_webhookIdentifier.Value, payload);
             }
@@ -609,6 +610,26 @@ namespace Content.Server.GameTicking
             if (proto.Sound != null)
                 SoundSystem.Play(proto.Sound.GetSound(), Filter.Broadcast());
         }
+
+        private async void SendRoundStartedDiscordMessage()
+        {
+            try
+            {
+                if (_webhookIdentifier == null)
+                    return;
+
+                var mapName = _gameMapManager.GetSelectedMap()?.MapName ?? Loc.GetString("discord-round-notifications-unknown-map");
+                var content = Loc.GetString("discord-round-notifications-started", ("id", RoundId), ("map", mapName));
+
+                var payload = new WebhookPayload { Content = content };
+
+                await _discord.CreateMessage(_webhookIdentifier.Value, payload);
+            }
+            catch (Exception e)
+            {
+                Log.Error($"Error while sending discord round start message:\n{e}");
+            }
+        }
     }
 
     public enum GameRunLevel
diff --git a/Content.Shared/CCVar/CCVars.cs b/Content.Shared/CCVar/CCVars.cs
index 14357e7f26..8cad414a56 100644
--- a/Content.Shared/CCVar/CCVars.cs
+++ b/Content.Shared/CCVar/CCVars.cs
@@ -344,14 +344,14 @@ namespace Content.Shared.CCVar
         /// <summary>
         /// URL of the Discord webhook which will relay round restart messages.
         /// </summary>
-        public static readonly CVarDef<string> DiscordRoundRestartWebhook =
-            CVarDef.Create("discord.round_restart_webhook", string.Empty, CVar.SERVERONLY);
+        public static readonly CVarDef<string> DiscordRoundUpdateWebhook =
+            CVarDef.Create("discord.round_update_webhook", string.Empty, CVar.SERVERONLY);
 
         /// <summary>
         /// Role id for the Discord webhook to ping when the round ends.
         /// </summary>
-        public static readonly CVarDef<long> DiscordRoundEndRoleWebhook =
-            CVarDef.Create("discord.round_end_role", 0L, CVar.SERVERONLY);
+        public static readonly CVarDef<string> DiscordRoundEndRoleWebhook =
+            CVarDef.Create("discord.round_end_role", string.Empty, CVar.SERVERONLY);
 
         /*
          * Suspicion
diff --git a/Resources/Locale/en-US/discord/round-notifications.ftl b/Resources/Locale/en-US/discord/round-notifications.ftl
new file mode 100644
index 0000000000..a9a3d5fb50
--- /dev/null
+++ b/Resources/Locale/en-US/discord/round-notifications.ftl
@@ -0,0 +1,5 @@
+discord-round-notifications-new = A new round is starting!
+discord-round-notifications-started = Round #{$id} on map "{$map}" started.
+discord-round-notifications-end = Round #{$id} has ended. It lasted for {$hours} hours, {$minutes} minutes, and {$seconds} seconds.
+discord-round-notifications-end-ping = <@&{$roleId}>, the server will reboot shortly!
+discord-round-notifications-unknown-map = Unknown