diff --git a/Content.Server/Chat/Commands/SayCommand.cs b/Content.Server/Chat/Commands/SayCommand.cs
index f53302fb75..5a31e561d7 100644
--- a/Content.Server/Chat/Commands/SayCommand.cs
+++ b/Content.Server/Chat/Commands/SayCommand.cs
@@ -36,6 +36,7 @@ namespace Content.Server.Chat.Commands
                 return;
 
             var chat = IoCManager.Resolve<IChatManager>();
+            var chatSanitizer = IoCManager.Resolve<IChatSanitizationManager>();
             var playerEntity = player.AttachedEntity;
 
             if (playerEntity == null)
@@ -62,7 +63,11 @@ namespace Content.Server.Chat.Commands
                     return;
                 }
 
-                chat.EntitySay(mindComponent.OwnedEntity, message);
+                var emote = chatSanitizer.TrySanitizeOutSmilies(message, mindComponent.OwnedEntity, out var sanitized, out var emoteStr);
+                if (sanitized.Length != 0)
+                    chat.EntitySay(mindComponent.OwnedEntity, sanitized);
+                if (emote)
+                    chat.EntityMe(mindComponent.OwnedEntity, emoteStr!);
             }
 
         }
diff --git a/Content.Server/Chat/Managers/ChatSanitizationManager.cs b/Content.Server/Chat/Managers/ChatSanitizationManager.cs
new file mode 100644
index 0000000000..65a4cc04ba
--- /dev/null
+++ b/Content.Server/Chat/Managers/ChatSanitizationManager.cs
@@ -0,0 +1,97 @@
+using System;
+using System.Collections.Generic;
+using System.Diagnostics.CodeAnalysis;
+using System.Globalization;
+using Content.Shared.CCVar;
+using Robust.Shared.Configuration;
+using Robust.Shared.GameObjects;
+using Robust.Shared.IoC;
+using Robust.Shared.Localization;
+
+namespace Content.Server.Chat.Managers;
+
+public class ChatSanitizationManager : IChatSanitizationManager
+{
+    [Dependency] private IConfigurationManager _configurationManager = default!;
+
+    private static readonly Dictionary<string, string> SmileyToEmote = new()
+    {
+        // I could've done this with regex, but felt it wasn't the right idea.
+        { ":)", "chatsan-smiles" },
+        { ":]", "chatsan-smiles" },
+        { "=)", "chatsan-smiles" },
+        { "=]", "chatsan-smiles" },
+        { "(:", "chatsan-smiles" },
+        { "[:", "chatsan-smiles" },
+        { "(=", "chatsan-smiles" },
+        { "[=", "chatsan-smiles" },
+        { ":(", "chatsan-frowns" },
+        { ":[", "chatsan-frowns" },
+        { "=(", "chatsan-frowns" },
+        { "=[", "chatsan-frowns" },
+        { "):", "chatsan-frowns" },
+        { ")=", "chatsan-frowns" },
+        { "]:", "chatsan-frowns" },
+        { "]=", "chatsan-frowns" },
+        { ":D", "chatsan-smiles-widely" },
+        { "D:", "chatsan-frowns-deeply" },
+        { ":O", "chatsan-surprised" },
+        { ":3", "chatsan-smiles" }, //nope
+        { ":S", "chatsan-uncertain" },
+        { ":>", "chatsan-grins" },
+        { ":<", "chatsan-pouts" },
+        { "xD", "chatsan-laughs" },
+        { ";-;", "chatsan-cries" },
+        { ";_;", "chatsan-cries" },
+        { ":u", "chatsan-smiles-smugly" },
+        { ":v", "chatsan-smiles-smugly" },
+        { ">:i", "chatsan-annoyed" },
+        { ":i", "chatsan-sighs" },
+        { ":|", "chatsan-sighs" },
+        { ":p", "chatsan-stick-out-tongue" },
+        { ":b", "chatsan-stick-out-tongue" },
+        { "0-0", "chatsan-wide-eyed" },
+        { "o-o", "chatsan-wide-eyed" },
+        { "o.o", "chatsan-wide-eyed" },
+        { "._.", "chatsan-surprised" },
+        { ".-.", "chatsan-confused" },
+        { "-_-", "chatsan-unimpressed" },
+        { "o/", "chatsan-waves" },
+        { "^^/", "chatsan-waves" },
+        { ":/", "chatsan-uncertain" },
+        { ":\\", "chatsan-uncertain" },
+    };
+
+    private bool doSanitize = false;
+
+    public void Initialize()
+    {
+        _configurationManager.OnValueChanged(CCVars.ChatSanitizerEnabled, x => doSanitize = x, true);
+    }
+
+    public bool TrySanitizeOutSmilies(string input, IEntity speaker, out string sanitized, [NotNullWhen(true)] out string? emote)
+    {
+        if (!doSanitize)
+        {
+            sanitized = input;
+            emote = null;
+            return false;
+        }
+
+        input = input.TrimEnd();
+
+        foreach (var (smiley, replacement) in SmileyToEmote)
+        {
+            if (input.EndsWith(smiley, true, CultureInfo.InvariantCulture))
+            {
+                sanitized = input.Remove(input.Length - smiley.Length).TrimEnd();
+                emote = Loc.GetString(replacement, ("ent", speaker));
+                return true;
+            }
+        }
+
+        sanitized = input;
+        emote = null;
+        return false;
+    }
+}
diff --git a/Content.Server/Chat/Managers/IChatSanitizationManager.cs b/Content.Server/Chat/Managers/IChatSanitizationManager.cs
new file mode 100644
index 0000000000..ebd2a79b03
--- /dev/null
+++ b/Content.Server/Chat/Managers/IChatSanitizationManager.cs
@@ -0,0 +1,11 @@
+using System.Diagnostics.CodeAnalysis;
+using Robust.Shared.GameObjects;
+
+namespace Content.Server.Chat.Managers;
+
+public interface IChatSanitizationManager
+{
+    public void Initialize();
+
+    public bool TrySanitizeOutSmilies(string input, IEntity speaker, out string sanitized, [NotNullWhen(true)] out string? emote);
+}
diff --git a/Content.Server/Entry/EntryPoint.cs b/Content.Server/Entry/EntryPoint.cs
index 0628a1e04a..db052cd6e3 100644
--- a/Content.Server/Entry/EntryPoint.cs
+++ b/Content.Server/Entry/EntryPoint.cs
@@ -62,6 +62,7 @@ namespace Content.Server.Entry
             _euiManager = IoCManager.Resolve<EuiManager>();
             _voteManager = IoCManager.Resolve<IVoteManager>();
 
+            IoCManager.Resolve<IChatSanitizationManager>().Initialize();
             IoCManager.Resolve<IChatManager>().Initialize();
 
             var playerManager = IoCManager.Resolve<IPlayerManager>();
diff --git a/Content.Server/IoC/ServerContentIoC.cs b/Content.Server/IoC/ServerContentIoC.cs
index 6152a9d3ae..b44ea2fd57 100644
--- a/Content.Server/IoC/ServerContentIoC.cs
+++ b/Content.Server/IoC/ServerContentIoC.cs
@@ -34,6 +34,7 @@ namespace Content.Server.IoC
         public static void Register()
         {
             IoCManager.Register<IChatManager, ChatManager>();
+            IoCManager.Register<IChatSanitizationManager, ChatSanitizationManager>();
             IoCManager.Register<IMoMMILink, MoMMILink>();
             IoCManager.Register<ISandboxManager, SandboxManager>();
             IoCManager.Register<IModuleManager, ServerModuleManager>();
diff --git a/Content.Shared/CCVar/CCVars.cs b/Content.Shared/CCVar/CCVars.cs
index 74d69a3451..3986dfbfd4 100644
--- a/Content.Shared/CCVar/CCVars.cs
+++ b/Content.Shared/CCVar/CCVars.cs
@@ -553,6 +553,9 @@ namespace Content.Shared.CCVar
         public static readonly CVarDef<int> ChatMaxMessageLength =
             CVarDef.Create("chat.max_message_length", 1000, CVar.SERVER | CVar.REPLICATED);
 
+        public static readonly CVarDef<bool> ChatSanitizerEnabled =
+            CVarDef.Create("chat.chat_sanitizer_enabled", true, CVar.SERVERONLY);
+
         /*
          * AFK
          */
diff --git a/Resources/Locale/en-US/chat/sanitizer-replacements.ftl b/Resources/Locale/en-US/chat/sanitizer-replacements.ftl
new file mode 100644
index 0000000000..0f98a18fd3
--- /dev/null
+++ b/Resources/Locale/en-US/chat/sanitizer-replacements.ftl
@@ -0,0 +1,19 @@
+chatsan-smiles = smiles
+chatsan-frowns = frowns
+chatsan-smiles-widely = smiles widely
+chatsan-frowns-deeply = frowns deeply
+chatsan-surprised = looks surprised
+chatsan-uncertain = looks uncertain
+chatsan-grins = grins
+chatsan-pouts = pouts
+chatsan-laughs = laughs
+chatsan-cries = cries
+chatsan-smiles-smugly = smiles smugly
+chatsan-annoyed = looks annoyed
+chatsan-sighs = sighs
+chatsan-stick-out-tongue = sticks { POSS-ADJ($ent) } tongue out
+chatsan-wide-eyed = looks shocked
+chatsan-surprised = looks surpised
+chatsan-confused = looks confused
+chatsan-unimpressed = seems unimpressed
+chatsan-waves = waves