diff --git a/Content.Server/Chat/Managers/ChatSanitizationManager.cs b/Content.Server/Chat/Managers/ChatSanitizationManager.cs
index c9566244357..c5ac2d2935b 100644
--- a/Content.Server/Chat/Managers/ChatSanitizationManager.cs
+++ b/Content.Server/Chat/Managers/ChatSanitizationManager.cs
@@ -33,7 +33,7 @@ public sealed class ChatSanitizationManager : IChatSanitizationManager
         { ":D", "chatsan-smiles-widely" },
         { "D:", "chatsan-frowns-deeply" },
         { ":O", "chatsan-surprised" },
-        { ":3", "chatsan-smiles" }, //nope
+        { ":3", "chatsan-smiles" },
         { ":S", "chatsan-uncertain" },
         { ":>", "chatsan-grins" },
         { ":<", "chatsan-pouts" },
diff --git a/Content.Server/Chat/Systems/ChatSystem.cs b/Content.Server/Chat/Systems/ChatSystem.cs
index 94af12ea201..6b000532bec 100644
--- a/Content.Server/Chat/Systems/ChatSystem.cs
+++ b/Content.Server/Chat/Systems/ChatSystem.cs
@@ -263,6 +263,8 @@ public void TrySendInGameICMessage(
             }
         }
 
+        message = FormattedMessage.EscapeText(message);
+
         // Otherwise, send whatever type.
         switch (desiredType)
         {
@@ -408,7 +410,7 @@ private void SendEntitySpeak(
             return;
 
         // The original message
-        var message = TransformSpeech(source, FormattedMessage.RemoveMarkup(originalMessage), language);
+        var message = TransformSpeech(source, FormattedMessage.RemoveMarkupPermissive(originalMessage), language);
 
         if (message.Length == 0)
             return;
@@ -481,7 +483,7 @@ private void SendEntityWhisper(
         if (!_actionBlocker.CanSpeak(source) && !ignoreActionBlocker)
             return;
 
-        var message = TransformSpeech(source, FormattedMessage.RemoveMarkup(originalMessage), language);
+        var message = TransformSpeech(source, FormattedMessage.RemoveMarkupPermissive(originalMessage), language);
         if (message.Length == 0)
             return;
 
@@ -517,7 +519,7 @@ private void SendEntityWhisper(
 
             var canUnderstandLanguage = _language.CanUnderstand(listener, language.ID);
             // How the entity perceives the message depends on whether it can understand its language
-            var perceivedMessage = FormattedMessage.EscapeText(canUnderstandLanguage ? message : languageObfuscatedMessage);
+            var perceivedMessage = canUnderstandLanguage ? message : languageObfuscatedMessage;
 
             // Result is the intermediate message derived from the perceived one via obfuscation
             // Wrapped message is the result wrapped in an "x says y" string
@@ -544,7 +546,7 @@ private void SendEntityWhisper(
             _chatManager.ChatMessageToOne(ChatChannel.Whisper, result, wrappedMessage, source, false, session.Channel);
         }
 
-        var replayWrap = WrapWhisperMessage(source, "chat-manager-entity-whisper-wrap-message", name, FormattedMessage.EscapeText(message), language);
+        var replayWrap = WrapWhisperMessage(source, "chat-manager-entity-whisper-wrap-message", name, message, language);
         _replay.RecordServerMessage(new ChatMessage(ChatChannel.Whisper, message, replayWrap, GetNetEntity(source), null, MessageRangeHideChatForReplay(range)));
 
         var ev = new EntitySpokeEvent(source, message, channel, true, language);
@@ -591,7 +593,7 @@ private void SendEntityEmote(
         var wrappedMessage = Loc.GetString("chat-manager-entity-me-wrap-message",
             ("entityName", name),
             ("entity", ent),
-            ("message", FormattedMessage.RemoveMarkup(action)));
+            ("message", FormattedMessage.RemoveMarkupPermissive(action)));
 
         if (checkEmote)
             TryEmoteChatInput(source, action);
@@ -771,8 +773,10 @@ private bool CanSendInGame(string message, IConsoleShell? shell = null, ICommonS
     // ReSharper disable once InconsistentNaming
     private string SanitizeInGameICMessage(EntityUid source, string message, out string? emoteStr, bool capitalize = true, bool punctuate = false, bool capitalizeTheWordI = true)
     {
-        var newMessage = message.Trim();
-        newMessage = SanitizeMessageReplaceWords(newMessage);
+        var newMessage = SanitizeMessageReplaceWords(message.Trim());
+
+        GetRadioKeycodePrefix(source, newMessage, out newMessage, out var prefix);
+        _sanitizer.TrySanitizeOutSmilies(newMessage, source, out newMessage, out emoteStr);
 
         if (capitalize)
             newMessage = SanitizeMessageCapital(newMessage);
@@ -781,9 +785,7 @@ private string SanitizeInGameICMessage(EntityUid source, string message, out str
         if (punctuate)
             newMessage = SanitizeMessagePeriod(newMessage);
 
-        _sanitizer.TrySanitizeOutSmilies(newMessage, source, out newMessage, out emoteStr);
-
-        return newMessage;
+        return prefix + newMessage;
     }
 
     private string SanitizeInGameOOCMessage(string message)
diff --git a/Content.Shared/Chat/SharedChatSystem.cs b/Content.Shared/Chat/SharedChatSystem.cs
index ff2a30ccbdb..fe5da426d9d 100644
--- a/Content.Shared/Chat/SharedChatSystem.cs
+++ b/Content.Shared/Chat/SharedChatSystem.cs
@@ -86,6 +86,35 @@ public SpeechVerbPrototype GetSpeechVerb(EntityUid source, string message, Speec
         return current ?? _prototypeManager.Index(speech.SpeechVerb);
     }
 
+    /// <summary>
+    /// Splits the input message into a radio prefix part and the rest to preserve it during sanitization.
+    /// </summary>
+    /// <remarks>
+    /// This is primarily for the chat emote sanitizer, which can match against ":b" as an emote, which is a valid radio keycode.
+    /// </remarks>
+    public void GetRadioKeycodePrefix(EntityUid source,
+        string input,
+        out string output,
+        out string prefix)
+    {
+        prefix = string.Empty;
+        output = input;
+
+        // If the string is less than 2, then it's probably supposed to be an emote.
+        // No one is sending empty radio messages!
+        if (input.Length <= 2)
+            return;
+
+        if (!(input.StartsWith(RadioChannelPrefix) || input.StartsWith(RadioChannelAltPrefix)))
+            return;
+
+        if (!_keyCodes.TryGetValue(input[1], out _))
+            return;
+
+        prefix = input[..2];
+        output = input[2..];
+    }
+
     /// <summary>
     ///     Attempts to resolve radio prefixes in chat messages (e.g., remove a leading ":e" and resolve the requested
     ///     channel. Returns true if a radio message was attempted, even if the channel is invalid.
diff --git a/Content.Shared/Preferences/HumanoidCharacterProfile.cs b/Content.Shared/Preferences/HumanoidCharacterProfile.cs
index 56684deb19e..ac3c5c8dd11 100644
--- a/Content.Shared/Preferences/HumanoidCharacterProfile.cs
+++ b/Content.Shared/Preferences/HumanoidCharacterProfile.cs
@@ -23,7 +23,7 @@ namespace Content.Shared.Preferences;
 [Serializable, NetSerializable]
 public sealed partial class HumanoidCharacterProfile : ICharacterProfile
 {
-    private static readonly Regex RestrictedNameRegex = new("[^A-Z,a-z,0-9, -]");
+    private static readonly Regex RestrictedNameRegex = new(@"[^A-Za-z0-9 '\-]");
     private static readonly Regex ICNameCaseRegex = new(@"^(?<word>\w)|\b(?<word>\w)(?=\w*$)");
 
     public const int MaxNameLength = 64;