diff --git a/CHANGELOG.md b/CHANGELOG.md
index 31bb1005..86dc96b9 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -17,6 +17,7 @@ This is the rolling changelog for TShock for Terraria. Use past tense when addin
 * Added handling to the PlayerChat hook event. (@QuiCM - Thanks for the suggestion @Arthri)
 * Changed the spawnboss command to support silent command specifiers. (@QuiCM, suggested by @nojomyth-dev)
 * Updated /godmode to use Journey Mode's Godmode power instead of healing on damage. (requested by @tlworks, backported by @bartico6, implemented preemptive bugfix for creative powers mentioned by @Stealownz)
+* Fixed /r attempting to send messages to players that have since disconnected. (@bartico6, reported by @Arthri)
 
 ## TShock 4.5.0.1
 * Fixed conversion from old to new ban system for MySQL hosted ban databases. (@DeathCradle, @ATFGK)
diff --git a/TShockAPI/Commands.cs b/TShockAPI/Commands.cs
index 3bff1f2b..7d2a42d2 100644
--- a/TShockAPI/Commands.cs
+++ b/TShockAPI/Commands.cs
@@ -5366,12 +5366,16 @@ namespace TShockAPI
 			{
 				args.Player.SendErrorMessage("You are muted.");
 			}
-			else if (args.Player.LastWhisper != null)
+			else if (args.Player.LastWhisper != null && args.Player.LastWhisper.Active)
 			{
 				var msg = string.Join(" ", args.Parameters);
 				args.Player.LastWhisper.SendMessage(String.Format("<From {0}> {1}", args.Player.Name, msg), Color.MediumPurple);
 				args.Player.SendMessage(String.Format("<To {0}> {1}", args.Player.LastWhisper.Name, msg), Color.MediumPurple);
 			}
+			else if (args.Player.LastWhisper != null)
+			{
+				args.Player.SendErrorMessage("The player you're attempting to reply to is no longer online.");
+			}
 			else
 			{
 				args.Player.SendErrorMessage("You haven't previously received any whispers. Please use {0}whisper to whisper to other people.", Specifier);