diff --git a/Classes/AwardedLoot.lua b/Classes/AwardedLoot.lua
index e45d4b84..46a273bb 100644
--- a/Classes/AwardedLoot.lua
+++ b/Classes/AwardedLoot.lua
@@ -828,6 +828,11 @@ end
 function AwardedLoot:initiateTrade(AwardDetails)
     local tradingPartner = AwardDetails.awardedTo;
 
+    -- No need to trade with yourself
+    if (GL:iEquals(tradingPartner, GL.User.fqn)) then
+        return;
+    end
+
     -- Check whether we have the item in our inventory, no point opening a trade window if not
     local itemPositionInBag = GL:findBagIdAndSlotForItem(AwardDetails.itemLink or AwardDetails.itemID);
     if (GL:empty(itemPositionInBag)) then
@@ -843,9 +848,22 @@ function AwardedLoot:initiateTrade(AwardDetails)
 
     if (not TradeFrame:IsShown()) then
         -- Open a trade window with the winner
-        GL.TradeWindow:open(tradingPartner, function ()
+        GL.TradeWindow:open(tradingPartner, function (success)
+            if (not success) then
+                if (Settings:get("AwardingLoot.notifyOfFailedTradeStart")) then
+                    GL:sendChatMessage(
+                        GL:printfn(L.CHAT.TRADE_START_FAILED, {
+                            item = AwardDetails.itemLink or "?",
+                        }),
+                        "WHISPER", nil, tradingPartner
+                    );
+                end
+
+                return;
+            end
+
             self:tradeInitiated();
-        end);
+        end, true);
 
     -- We're already trading with the winner
     elseif (GL:tableGet(GL.TradeWindow, "State.partner") == tradingPartner) then
diff --git a/Classes/TradeWindow.lua b/Classes/TradeWindow.lua
index 01571ea1..e8f4cc68 100644
--- a/Classes/TradeWindow.lua
+++ b/Classes/TradeWindow.lua
@@ -70,7 +70,7 @@ function TradeWindow:open(playerName, callback, allwaysExecuteCallback)
         if (type(callback) == "function"
             and (allwaysExecuteCallback or self.Sate.partner == playerName)
         ) then
-            callback();
+            callback(GL:iEquals(self.Sate.partner, playerName));
         end
 
         return;
@@ -85,7 +85,7 @@ function TradeWindow:open(playerName, callback, allwaysExecuteCallback)
             GL.Events:unregister("TradeWindowTradeShowCallbackListener");
 
             if (allwaysExecuteCallback) then
-                callback();
+                callback(false);
             end
         end, 1);
 
@@ -100,10 +100,10 @@ function TradeWindow:open(playerName, callback, allwaysExecuteCallback)
             if (allwaysExecuteCallback
                 or (
                     TradeFrame:IsShown()
-                    and self.Sate.partner == playerName
+                    and GL:iEquals(self.Sate.partner, playerName)
                 )
             ) then
-                callback();
+                callback(true);
             end
         end);
     end
diff --git a/Data/DefaultSettings.lua b/Data/DefaultSettings.lua
index 9eeb6ff4..fc349d75 100644
--- a/Data/DefaultSettings.lua
+++ b/Data/DefaultSettings.lua
@@ -88,6 +88,7 @@ GL.Data.DefaultSettings = {
         awardMessagesEnabled = true,
         awardOnReceive = false,
         awardOnReceiveMinimumQuality = 4,
+        notifyOfFailedTradeStart = true,
         skipAwardConfirmationDialog = false,
     },
     ExportingLoot = {
diff --git a/Data/Localizations/chat.lua b/Data/Localizations/chat.lua
index 4e024fb1..50b596cb 100644
--- a/Data/Localizations/chat.lua
+++ b/Data/Localizations/chat.lua
@@ -89,6 +89,7 @@ L.CHAT = {
         ROLLING_TMB_INFO = "These players have the highest %s prio: %s", -- First %s can be TMB/DFT/CPR
 
         --[[ TradeWindow / Trade ]]
+        TRADE_START_FAILED = "I tried to trade you, but was unsuccessful - trade me for ${item} asap!",
         TRADE_TO = "%s to %s",
         TRADE_TO_PART = "to %s",
         TRADE_GAVE = "I gave %s",
@@ -204,6 +205,7 @@ L.CHAT = {
         ROLLING_TMB_INFO = "Die folgenden Spieler haben die höchste %s-Prio: %s", -- First %s can be TMB/DFT/CPR
 
         --[[ TradeWindow / Trade ]]
+        TRADE_START_FAILED = "I tried to trade you, but was unsuccessful - trade me for ${item} asap!",
         TRADE_TO = "%s an %s",
         TRADE_TO_PART = "an %s",
         TRADE_GAVE = "Ich habe %s gegeben",
@@ -319,6 +321,7 @@ L.CHAT = {
         ROLLING_TMB_INFO = "以下玩家的 %s 优先级最高：%s", -- First %s can be TMB/DFT/CPR
 
         --[[ TradeWindow / Trade ]]
+        TRADE_START_FAILED = "I tried to trade you, but was unsuccessful - trade me for ${item} asap!",
         TRADE_TO = "%s 给 %s",
         TRADE_TO_PART = "给 %s",
         TRADE_GAVE = "我给了%s",
@@ -434,6 +437,7 @@ L.CHAT = {
         ROLLING_TMB_INFO = "Los siguientes jugadores tienen el %s prio más alto: %s", -- First %s can be TMB/DFT/CPR
 
         --[[ TradeWindow / Trade ]]
+        TRADE_START_FAILED = "I tried to trade you, but was unsuccessful - trade me for ${item} asap!",
         TRADE_TO = "%s a %s",
         TRADE_TO_PART = "a %s",
         TRADE_GAVE = "Le di %s",
@@ -549,6 +553,7 @@ L.CHAT = {
         ROLLING_TMB_INFO = "Les joueurs suivants ont la plus haute prio %s : %s", -- First %s can be TMB/DFT/CPR
 
         --[[ TradeWindow / Trade ]]
+        TRADE_START_FAILED = "I tried to trade you, but was unsuccessful - trade me for ${item} asap!",
         TRADE_TO = "%s à %s",
         TRADE_TO_PART = "à %s",
         TRADE_GAVE = "J'ai donné %s",
@@ -664,6 +669,7 @@ L.CHAT = {
         ROLLING_TMB_INFO = "I seguenti giocatori hanno il vantaggio di %s più alto: %s", -- First %s can be TMB/DFT/CPR
 
         --[[ TradeWindow / Trade ]]
+        TRADE_START_FAILED = "I tried to trade you, but was unsuccessful - trade me for ${item} asap!",
         TRADE_TO = "Da %s a %s",
         TRADE_TO_PART = "a %s",
         TRADE_GAVE = "Ho dato %s",
@@ -779,6 +785,7 @@ L.CHAT = {
         ROLLING_TMB_INFO = "다음 플레이어의 %s 우선 순위가 가장 높습니다: %s", -- First %s can be TMB/DFT/CPR
 
         --[[ TradeWindow / Trade ]]
+        TRADE_START_FAILED = "I tried to trade you, but was unsuccessful - trade me for ${item} asap!",
         TRADE_TO = "%s ~ %s",
         TRADE_TO_PART = "%s에게",
         TRADE_GAVE = "%s을(를) 줬습니다",
@@ -894,6 +901,7 @@ L.CHAT = {
         ROLLING_TMB_INFO = "Os seguintes jogadores têm o maior %s prio: %s", -- First %s can be TMB/DFT/CPR
 
         --[[ TradeWindow / Trade ]]
+        TRADE_START_FAILED = "I tried to trade you, but was unsuccessful - trade me for ${item} asap!",
         TRADE_TO = "%s para %s",
         TRADE_TO_PART = "para% s",
         TRADE_GAVE = "Eu dei %s",
@@ -1009,6 +1017,7 @@ L.CHAT = {
         ROLLING_TMB_INFO = "Следующие игроки имеют самый высокий процент %s: %s", -- First %s can be TMB/DFT/CPR
 
         --[[ TradeWindow / Trade ]]
+        TRADE_START_FAILED = "I tried to trade you, but was unsuccessful - trade me for ${item} asap!",
         TRADE_TO = "от %s до %s",
         TRADE_TO_PART = "до %s",
         TRADE_GAVE = "я дал %s",
@@ -1124,6 +1133,7 @@ L.CHAT = {
         ROLLING_TMB_INFO = "以下玩家的 %s 優先順序最高：%s", -- First %s can be TMB/DFT/CPR
 
         --[[ TradeWindow / Trade ]]
+        TRADE_START_FAILED = "I tried to trade you, but was unsuccessful - trade me for ${item} asap!",
         TRADE_TO = "%s 至 %s",
         TRADE_TO_PART = "至 %s",
         TRADE_GAVE = "我給了%s",
diff --git a/Interface/Settings/AwardingLoot.lua b/Interface/Settings/AwardingLoot.lua
index 1180f1fb..32267026 100644
--- a/Interface/Settings/AwardingLoot.lua
+++ b/Interface/Settings/AwardingLoot.lua
@@ -45,6 +45,11 @@ function AwardingLoot:draw(Parent)
             description = "If you award an item from your inventory then automatically trade the winner if he's within reach",
             setting = "AwardingLoot.autoTradeAfterAwardingAnItem",
         },
+        {
+            label = "Notify in case trade fails",
+            description = "Send a whisper to the winner if you couldn't open a trade window with them",
+            setting = "AwardingLoot.notifyOfFailedTradeStart",
+        },
         {
             label = "Skip award confirmation dialog",
             setting = "AwardingLoot.skipAwardConfirmationDialog",