diff --git a/Content.Server/Administration/Systems/BwoinkSystem.cs b/Content.Server/Administration/Systems/BwoinkSystem.cs
index 107f299dbf..72e78435e6 100644
--- a/Content.Server/Administration/Systems/BwoinkSystem.cs
+++ b/Content.Server/Administration/Systems/BwoinkSystem.cs
@@ -3,10 +3,10 @@ using System.Net.Http;
 using System.Text;
 using System.Text.Json;
 using System.Text.Json.Nodes;
-using System.Text.Json.Serialization;
 using System.Text.RegularExpressions;
 using System.Threading.Tasks;
 using Content.Server.Administration.Managers;
+using Content.Server.Discord;
 using Content.Server.GameTicking;
 using Content.Server.Players;
 using Content.Shared.Administration;
@@ -337,13 +337,13 @@ namespace Content.Server.Administration.Systems
             {
                 Username = username,
                 AvatarUrl = string.IsNullOrWhiteSpace(_avatarUrl) ? null : _avatarUrl,
-                Embeds = new List<Embed>
+                Embeds = new List<WebhookEmbed>
                 {
                     new()
                     {
                         Description = messages,
                         Color = color,
-                        Footer = new EmbedFooter
+                        Footer = new WebhookEmbedFooter
                         {
                             Text = $"{serverName} ({round})",
                             IconUrl = string.IsNullOrWhiteSpace(_footerIconUrl) ? null : _footerIconUrl
@@ -469,75 +469,6 @@ namespace Content.Server.Administration.Systems
             stringbuilder.Append(message);
             return stringbuilder.ToString();
         }
-
-        // https://discord.com/developers/docs/resources/channel#message-object-message-structure
-        private struct WebhookPayload
-        {
-            [JsonPropertyName("username")]
-            public string Username { get; set; } = "";
-
-            [JsonPropertyName("avatar_url")]
-            public string? AvatarUrl { get; set; } = "";
-
-            [JsonPropertyName("embeds")]
-            public List<Embed>? Embeds { get; set; } = null;
-
-            [JsonPropertyName("allowed_mentions")]
-            public Dictionary<string, string[]> AllowedMentions { get; set; } =
-                new()
-                {
-                    { "parse", Array.Empty<string>() },
-                };
-
-            public WebhookPayload()
-            {
-            }
-        }
-
-        // https://discord.com/developers/docs/resources/channel#embed-object-embed-structure
-        private struct Embed
-        {
-            [JsonPropertyName("description")]
-            public string Description { get; set; } = "";
-
-            [JsonPropertyName("color")]
-            public int Color { get; set; } = 0;
-
-            [JsonPropertyName("footer")]
-            public EmbedFooter? Footer { get; set; } = null;
-
-            public Embed()
-            {
-            }
-        }
-
-        // https://discord.com/developers/docs/resources/channel#embed-object-embed-footer-structure
-        private struct EmbedFooter
-        {
-            [JsonPropertyName("text")]
-            public string Text { get; set; } = "";
-
-            [JsonPropertyName("icon_url")]
-            public string? IconUrl { get; set; }
-
-            public EmbedFooter()
-            {
-            }
-        }
-
-        // https://discord.com/developers/docs/resources/webhook#webhook-object-webhook-structure
-        private struct WebhookData
-        {
-            [JsonPropertyName("guild_id")]
-            public string? GuildId { get; set; } = null;
-
-            [JsonPropertyName("channel_id")]
-            public string? ChannelId { get; set; } = null;
-
-            public WebhookData()
-            {
-            }
-        }
     }
 }
 
diff --git a/Content.Server/Discord/DiscordWebhook.cs b/Content.Server/Discord/DiscordWebhook.cs
new file mode 100644
index 0000000000..d8a9318444
--- /dev/null
+++ b/Content.Server/Discord/DiscordWebhook.cs
@@ -0,0 +1,101 @@
+using System.Net.Http;
+using System.Net.Http.Json;
+using System.Threading.Tasks;
+
+namespace Content.Server.Discord;
+
+public sealed class DiscordWebhook : IPostInjectInit
+{
+    [Dependency] private readonly ILogManager _log = default!;
+
+    private const string BaseUrl = "https://discord.com/api/v10/webhooks";
+    private readonly HttpClient _http = new();
+    private ISawmill _sawmill = default!;
+
+    private string GetUrl(WebhookIdentifier identifier)
+    {
+        return $"{BaseUrl}/{identifier.Id}/{identifier.Token}";
+    }
+
+    /// <summary>
+    ///     Gets the webhook data from the given webhook url.
+    /// </summary>
+    /// <param name="url">The url to get the data from.</param>
+    /// <returns>The webhook data returned from the url.</returns>
+    public async Task<WebhookData?> GetWebhook(string url)
+    {
+        try
+        {
+            return await _http.GetFromJsonAsync<WebhookData>(url);
+        }
+        catch
+        {
+            _sawmill.Error($"Error getting discord webhook data. Stack trace:\n{Environment.StackTrace}");
+            return null;
+        }
+    }
+
+    /// <summary>
+    ///     Gets the webhook data from the given webhook url.
+    /// </summary>
+    /// <param name="url">The url to get the data from.</param>
+    /// <param name="onComplete">The delegate to invoke with the obtained data, if any.</param>
+    public async void GetWebhook(string url, Action<WebhookData> onComplete)
+    {
+        if (await GetWebhook(url) is { } data)
+            onComplete(data);
+    }
+
+    /// <summary>
+    ///     Tries to get the webhook data from the given webhook url if it is not null or whitespace.
+    /// </summary>
+    /// <param name="url">The url to get the data from.</param>
+    /// <param name="onComplete">The delegate to invoke with the obtained data, if any.</param>
+    public async void TryGetWebhook(string url, Action<WebhookData> onComplete)
+    {
+        if (await GetWebhook(url) is { } data)
+            onComplete(data);
+    }
+
+    /// <summary>
+    ///     Creates a new webhook message with the given identifier and payload.
+    /// </summary>
+    /// <param name="identifier">The identifier for the webhook url.</param>
+    /// <param name="payload">The payload to create the message from.</param>
+    /// <returns>The response from Discord's API.</returns>
+    public async Task<HttpResponseMessage> CreateMessage(WebhookIdentifier identifier, WebhookPayload payload)
+    {
+        var url = $"{GetUrl(identifier)}?wait=true";
+        return await _http.PostAsJsonAsync(url, payload);
+    }
+
+    /// <summary>
+    ///     Deletes a webhook message with the given identifier and message id.
+    /// </summary>
+    /// <param name="identifier">The identifier for the webhook url.</param>
+    /// <param name="messageId">The message id to delete.</param>
+    /// <returns>The response from Discord's API.</returns>
+    public async Task<HttpResponseMessage> DeleteMessage(WebhookIdentifier identifier, ulong messageId)
+    {
+        var url = $"{GetUrl(identifier)}/messages/{messageId}";
+        return await _http.DeleteAsync(url);
+    }
+
+    /// <summary>
+    ///     Creates a new webhook message with the given identifier, message id and payload.
+    /// </summary>
+    /// <param name="identifier">The identifier for the webhook url.</param>
+    /// <param name="messageId">The message id to edit.</param>
+    /// <param name="payload">The payload used to edit the message.</param>
+    /// <returns>The response from Discord's API.</returns>
+    public async Task<HttpResponseMessage> EditMessage(WebhookIdentifier identifier, ulong messageId, WebhookPayload payload)
+    {
+        var url = $"{GetUrl(identifier)}/messages/{messageId}";
+        return await _http.PatchAsJsonAsync(url, payload);
+    }
+
+    void IPostInjectInit.PostInject()
+    {
+        _sawmill = _log.GetSawmill("DISCORD");
+    }
+}
diff --git a/Content.Server/Discord/WebhookData.cs b/Content.Server/Discord/WebhookData.cs
new file mode 100644
index 0000000000..5e23fa132c
--- /dev/null
+++ b/Content.Server/Discord/WebhookData.cs
@@ -0,0 +1,42 @@
+using System.Text.Json.Serialization;
+
+namespace Content.Server.Discord;
+
+// https://discord.com/developers/docs/resources/webhook#webhook-object-webhook-structure
+public struct WebhookData
+{
+    [JsonPropertyName("id")]
+    public ulong Id { get; set; }
+
+    [JsonPropertyName("type")]
+    public int Type { get; set; }
+
+    [JsonPropertyName("guild_id")]
+    public ulong? GuildId { get; set; }
+
+    [JsonPropertyName("channel_id")]
+    public ulong? ChannelId { get; set; }
+
+    [JsonPropertyName("user")]
+    public WebhookUser? User { get; set; }
+
+    [JsonPropertyName("name")]
+    public string? Name { get; set; }
+
+    [JsonPropertyName("avatar")]
+    public string? Avatar { get; set; }
+
+    [JsonPropertyName("token")]
+    public string Token { get; set; }
+
+    [JsonPropertyName("application_id")]
+    public ulong? ApplicationId { get; set; }
+
+    [JsonPropertyName("url")]
+    public string? Url { get; set; }
+
+    public WebhookIdentifier ToIdentifier()
+    {
+        return new WebhookIdentifier(Id, Token);
+    }
+}
diff --git a/Content.Server/Discord/WebhookEmbed.cs b/Content.Server/Discord/WebhookEmbed.cs
new file mode 100644
index 0000000000..8e0db0722c
--- /dev/null
+++ b/Content.Server/Discord/WebhookEmbed.cs
@@ -0,0 +1,20 @@
+using System.Text.Json.Serialization;
+
+namespace Content.Server.Discord;
+
+// https://discord.com/developers/docs/resources/channel#embed-object-embed-structure
+public struct WebhookEmbed
+{
+    [JsonPropertyName("description")]
+    public string Description { get; set; } = "";
+
+    [JsonPropertyName("color")]
+    public int Color { get; set; } = 0;
+
+    [JsonPropertyName("footer")]
+    public WebhookEmbedFooter? Footer { get; set; } = null;
+
+    public WebhookEmbed()
+    {
+    }
+}
diff --git a/Content.Server/Discord/WebhookEmbedFooter.cs b/Content.Server/Discord/WebhookEmbedFooter.cs
new file mode 100644
index 0000000000..9eda006ed2
--- /dev/null
+++ b/Content.Server/Discord/WebhookEmbedFooter.cs
@@ -0,0 +1,17 @@
+using System.Text.Json.Serialization;
+
+namespace Content.Server.Discord;
+
+// https://discord.com/developers/docs/resources/channel#embed-object-embed-footer-structure
+public struct WebhookEmbedFooter
+{
+    [JsonPropertyName("text")]
+    public string Text { get; set; } = "";
+
+    [JsonPropertyName("icon_url")]
+    public string? IconUrl { get; set; }
+
+    public WebhookEmbedFooter()
+    {
+    }
+}
diff --git a/Content.Server/Discord/WebhookIdentifier.cs b/Content.Server/Discord/WebhookIdentifier.cs
new file mode 100644
index 0000000000..9d0fba3d10
--- /dev/null
+++ b/Content.Server/Discord/WebhookIdentifier.cs
@@ -0,0 +1,3 @@
+namespace Content.Server.Discord;
+
+public record struct WebhookIdentifier(ulong Id, string Token);
diff --git a/Content.Server/Discord/WebhookMentions.cs b/Content.Server/Discord/WebhookMentions.cs
new file mode 100644
index 0000000000..da945b363e
--- /dev/null
+++ b/Content.Server/Discord/WebhookMentions.cs
@@ -0,0 +1,18 @@
+using System.Text.Json.Serialization;
+
+namespace Content.Server.Discord;
+
+public struct WebhookMentions
+{
+    [JsonPropertyName("parse")]
+    public HashSet<string> Parse { get; set; } = new();
+
+    public WebhookMentions()
+    {
+    }
+
+    public void AllowRoleMentions()
+    {
+        Parse.Add("roles");
+    }
+}
diff --git a/Content.Server/Discord/WebhookPayload.cs b/Content.Server/Discord/WebhookPayload.cs
new file mode 100644
index 0000000000..6300f86ad5
--- /dev/null
+++ b/Content.Server/Discord/WebhookPayload.cs
@@ -0,0 +1,29 @@
+using System.Text.Json.Serialization;
+
+namespace Content.Server.Discord;
+
+// https://discord.com/developers/docs/resources/channel#message-object-message-structure
+public struct WebhookPayload
+{
+    /// <summary>
+    ///     The message to send in the webhook. Maximum of 2000 characters.
+    /// </summary>
+    [JsonPropertyName("content")]
+    public string Content { get; set; } = "";
+
+    [JsonPropertyName("username")]
+    public string? Username { get; set; }
+
+    [JsonPropertyName("avatar_url")]
+    public string? AvatarUrl { get; set; } = "";
+
+    [JsonPropertyName("embeds")]
+    public List<WebhookEmbed>? Embeds { get; set; } = null;
+
+    [JsonPropertyName("allowed_mentions")]
+    public WebhookMentions AllowedMentions { get; set; } = new();
+
+    public WebhookPayload()
+    {
+    }
+}
diff --git a/Content.Server/Discord/WebhookUser.cs b/Content.Server/Discord/WebhookUser.cs
new file mode 100644
index 0000000000..3149c4f421
--- /dev/null
+++ b/Content.Server/Discord/WebhookUser.cs
@@ -0,0 +1,58 @@
+using System.Text.Json.Serialization;
+
+namespace Content.Server.Discord;
+
+// https://discord.com/developers/docs/resources/user#user-object
+public struct WebhookUser
+{
+    [JsonPropertyName("id")]
+    public ulong Id { get; set; }
+
+    [JsonPropertyName("username")]
+    public string Username { get; set; }
+
+    [JsonPropertyName("discriminator")]
+    public string Discriminator { get; set; }
+
+    [JsonPropertyName("global_name")]
+    public string? GlobalName { get; set; }
+
+    [JsonPropertyName("avatar")]
+    public string? Avatar { get; set; }
+
+    [JsonPropertyName("bot")]
+    public bool? Bot { get; set; }
+
+    [JsonPropertyName("system")]
+    public bool? System { get; set; }
+
+    [JsonPropertyName("mfa_enabled")]
+    public bool? MfaEnabled { get; set; }
+
+    [JsonPropertyName("banner")]
+    public string? Banner { get; set; }
+
+    [JsonPropertyName("accent_color")]
+    public int? AccentColor { get; set; }
+
+    [JsonPropertyName("locale")]
+    public string? Locale { get; set; }
+
+    [JsonPropertyName("verified")]
+    public bool? Verified { get; set; }
+
+    [JsonPropertyName("email")]
+    public string? Email { get; set; }
+
+    [JsonPropertyName("flags")]
+    public int? Flags { get; set; }
+
+    [JsonPropertyName("premium_type")]
+    public int? PremiumType { get; set; }
+
+    [JsonPropertyName("public_flags")]
+    public int? PublicFlags { get; set; }
+
+    [JsonPropertyName("avatar_decoration")]
+    public string? AvatarDecoration { get; set; }
+}
diff --git a/Content.Server/GameTicking/GameTicker.CVars.cs b/Content.Server/GameTicking/GameTicker.CVars.cs
index bc8dfb6783..8bb7f83856 100644
--- a/Content.Server/GameTicking/GameTicker.CVars.cs
+++ b/Content.Server/GameTicking/GameTicker.CVars.cs
@@ -1,3 +1,4 @@
+using Content.Server.Discord;
 using Content.Shared.CCVar;
 using Content.Shared.GameTicking;
 
@@ -26,6 +27,14 @@ namespace Content.Server.GameTicking
         [ViewVariables]
         public float MaxStationOffset { get; private set; } = 0f;
 
+        [ViewVariables]
+        public string? ServerName { get; private set; }
+
+        [ViewVariables]
+        private long? DiscordRoundEndRole { get; set; }
+
+        private WebhookIdentifier? _webhookIdentifier;
+
 #if EXCEPTION_TOLERANCE
         [ViewVariables]
         public int RoundStartFailShutdownCount { get; private set; } = 0;
@@ -51,6 +60,27 @@ namespace Content.Server.GameTicking
             _configurationManager.OnValueChanged(CCVars.StationOffset, value => StationOffset = value, true);
             _configurationManager.OnValueChanged(CCVars.StationRotation, value => StationRotation = value, true);
             _configurationManager.OnValueChanged(CCVars.MaxStationOffset, value => MaxStationOffset = value, true);
+            _configurationManager.OnValueChanged(CCVars.AdminLogsServerName, value =>
+            {
+                // TODO why tf is the server name on admin logs
+                ServerName = value;
+            }, true);
+            _configurationManager.OnValueChanged(CCVars.DiscordRoundRestartWebhook, value =>
+            {
+                if (!string.IsNullOrWhiteSpace(value))
+                {
+                    _discord.GetWebhook(value, data => _webhookIdentifier = data.ToIdentifier());
+                }
+            }, true);
+            _configurationManager.OnValueChanged(CCVars.DiscordRoundEndRoleWebhook, value =>
+            {
+                DiscordRoundEndRole = value;
+
+                if (value == 0)
+                {
+                    DiscordRoundEndRole = null;
+                }
+            }, true);
 #if EXCEPTION_TOLERANCE
             _configurationManager.OnValueChanged(CCVars.RoundStartFailShutdownCount, value => RoundStartFailShutdownCount = value, true);
 #endif
diff --git a/Content.Server/GameTicking/GameTicker.RoundFlow.cs b/Content.Server/GameTicking/GameTicker.RoundFlow.cs
index dbd029be84..a20cefb233 100644
--- a/Content.Server/GameTicking/GameTicker.RoundFlow.cs
+++ b/Content.Server/GameTicking/GameTicker.RoundFlow.cs
@@ -16,6 +16,7 @@ using Robust.Shared.Player;
 using Robust.Shared.Random;
 using Robust.Shared.Utility;
 using System.Linq;
+using Content.Server.Discord;
 using Content.Shared.Database;
 using Robust.Shared.Asynchronous;
 using PlayerData = Content.Server.Players.PlayerData;
@@ -24,6 +25,7 @@ namespace Content.Server.GameTicking
 {
     public sealed partial class GameTicker
     {
+        [Dependency] private readonly DiscordWebhook _discord = default!;
         [Dependency] private readonly ITaskManager _taskManager = default!;
 
         private static readonly Counter RoundNumberMetric = Metrics.CreateCounter(
@@ -303,6 +305,7 @@ namespace Content.Server.GameTicking
             LobbySong = _robustRandom.Pick(_lobbyMusicCollection.PickFiles).ToString();
 
             ShowRoundEndScoreboard(text);
+            SendRoundEndDiscordMessage();
         }
 
         public void ShowRoundEndScoreboard(string text = "")
@@ -385,6 +388,33 @@ namespace Content.Server.GameTicking
                 new SoundCollectionSpecifier("RoundEnd").GetSound()));
         }
 
+        private async void SendRoundEndDiscordMessage()
+        {
+            try
+            {
+                if (_webhookIdentifier == null)
+                    return;
+
+                var content = "The round has ended.";
+                if (DiscordRoundEndRole != null)
+                    content += $"\n\n<@&{DiscordRoundEndRole}>, the server will reboot shortly!";
+
+                var payload = new WebhookPayload
+                {
+                    Content = content,
+                    Username = ServerName,
+                };
+
+                payload.AllowedMentions.AllowRoleMentions();
+
+                await _discord.CreateMessage(_webhookIdentifier.Value, payload);
+            }
+            catch (Exception e)
+            {
+                Log.Error($"Error while sending discord round end message:\n{e}");
+            }
+        }
+
         public void RestartRound()
         {
             // If this game ticker is a dummy, do nothing!
@@ -426,6 +456,31 @@ namespace Content.Server.GameTicking
 
                 ReqWindowAttentionAll();
             }
+
+            SendRoundStartingDiscordMessage();
+        }
+
+        private async void SendRoundStartingDiscordMessage()
+        {
+            try
+            {
+                if (_webhookIdentifier == null)
+                    return;
+
+                var content = "New round starting!";
+
+                var payload = new WebhookPayload
+                {
+                    Content = content,
+                    Username = ServerName,
+                };
+
+                await _discord.CreateMessage(_webhookIdentifier.Value, payload);
+            }
+            catch (Exception e)
+            {
+                Log.Error($"Error while sending discord round starting message:\n{e}");
+            }
         }
 
         /// <summary>
diff --git a/Content.Server/IoC/ServerContentIoC.cs b/Content.Server/IoC/ServerContentIoC.cs
index 88d43213ba..ade4ecea52 100644
--- a/Content.Server/IoC/ServerContentIoC.cs
+++ b/Content.Server/IoC/ServerContentIoC.cs
@@ -6,6 +6,7 @@ using Content.Server.Afk;
 using Content.Server.Chat.Managers;
 using Content.Server.Connection;
 using Content.Server.Database;
+using Content.Server.Discord;
 using Content.Server.EUI;
 using Content.Server.GhostKick;
 using Content.Server.Info;
@@ -58,6 +59,7 @@ namespace Content.Server.IoC
             IoCManager.Register<UserDbDataManager>();
             IoCManager.Register<ServerInfoManager>();
             IoCManager.Register<PoissonDiskSampler>();
+            IoCManager.Register<DiscordWebhook>();
         }
     }
 }
diff --git a/Content.Shared/CCVar/CCVars.cs b/Content.Shared/CCVar/CCVars.cs
index ce768b418f..14357e7f26 100644
--- a/Content.Shared/CCVar/CCVars.cs
+++ b/Content.Shared/CCVar/CCVars.cs
@@ -341,6 +341,18 @@ namespace Content.Shared.CCVar
         public static readonly CVarDef<string> DiscordAHelpAvatar =
             CVarDef.Create("discord.ahelp_avatar", string.Empty, CVar.SERVERONLY);
 
+        /// <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);
+
+        /// <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);
+
         /*
          * Suspicion
          */