diff --git a/ArchiSteamFarm.OfficialPlugins.ItemsMatcher/Localization/Strings.Designer.cs b/ArchiSteamFarm.OfficialPlugins.ItemsMatcher/Localization/Strings.Designer.cs
index 63042578e..d22ca609d 100644
--- a/ArchiSteamFarm.OfficialPlugins.ItemsMatcher/Localization/Strings.Designer.cs
+++ b/ArchiSteamFarm.OfficialPlugins.ItemsMatcher/Localization/Strings.Designer.cs
@@ -68,5 +68,11 @@ namespace ArchiSteamFarm.OfficialPlugins.ItemsMatcher.Localization {
                 return ResourceManager.GetString("TradeOfferFailed", resourceCulture);
             }
         }
+        
+        internal static string ActivelyMatchingSomeConfirmationsFailed {
+            get {
+                return ResourceManager.GetString("ActivelyMatchingSomeConfirmationsFailed", resourceCulture);
+            }
+        }
     }
 }
diff --git a/ArchiSteamFarm.OfficialPlugins.ItemsMatcher/Localization/Strings.resx b/ArchiSteamFarm.OfficialPlugins.ItemsMatcher/Localization/Strings.resx
index 0949149bf..50f62b98e 100644
--- a/ArchiSteamFarm.OfficialPlugins.ItemsMatcher/Localization/Strings.resx
+++ b/ArchiSteamFarm.OfficialPlugins.ItemsMatcher/Localization/Strings.resx
@@ -78,4 +78,8 @@
 		<value>Failed to send a trade offer to bot {0} ({1}), moving on...</value>
 		<comment>{0} will be replaced by steam ID (number), {1} will be replaced by user's nickname'</comment>
 	</data>
+	<data name="ActivelyMatchingSomeConfirmationsFailed" xml:space="preserve">
+		<value>Some confirmations have failed, approximately {0} out of {1} trades were sent successfully.</value>
+		<comment>{0} will be replaced by amount of the trade offers that succeeded (number), {1} will be replaced by amount of the trade offers that were supposed to be sent in total (number)</comment>
+	</data>
 </root>
diff --git a/ArchiSteamFarm.OfficialPlugins.ItemsMatcher/RemoteCommunication.cs b/ArchiSteamFarm.OfficialPlugins.ItemsMatcher/RemoteCommunication.cs
index a00d8cc12..4fa4dd4e1 100644
--- a/ArchiSteamFarm.OfficialPlugins.ItemsMatcher/RemoteCommunication.cs
+++ b/ArchiSteamFarm.OfficialPlugins.ItemsMatcher/RemoteCommunication.cs
@@ -659,9 +659,16 @@ internal sealed class RemoteCommunication : IAsyncDisposable, IDisposable {
 
 		byte maxTradeHoldDuration = ASF.GlobalConfig?.MaxTradeHoldDuration ?? GlobalConfig.DefaultMaxTradeHoldDuration;
 
+		byte failuresInRow = 0;
 		uint matchedSets = 0;
 
 		foreach (ListedUser listedUser in listedUsers.Where(listedUser => (listedUser.SteamID != Bot.SteamID) && acceptedMatchableTypes.Any(listedUser.MatchableTypes.Contains) && !Bot.IsBlacklistedFromTrades(listedUser.SteamID)).OrderByDescending(static listedUser => listedUser.MatchEverything).ThenBy(static listedUser => listedUser.TotalInventoryCount)) {
+			if (failuresInRow >= WebBrowser.MaxTries) {
+				Bot.ArchiLogger.LogGenericWarning(string.Format(CultureInfo.CurrentCulture, Strings.WarningFailedWithError, $"{nameof(failuresInRow)} >= {WebBrowser.MaxTries}"));
+
+				break;
+			}
+
 			HashSet<(uint RealAppID, Asset.EType Type, Asset.ERarity Rarity)> wantedSets = ourTradableState.Keys.Where(set => listedUser.MatchableTypes.Contains(set.Type)).ToHashSet();
 
 			if (wantedSets.Count == 0) {
@@ -841,11 +848,15 @@ internal sealed class RemoteCommunication : IAsyncDisposable, IDisposable {
 
 				if (!success) {
 					// The user likely no longer has the items we need, this is fine, we can continue the matching with other ones
+					failuresInRow++;
+
 					Bot.ArchiLogger.LogGenericWarning(string.Format(CultureInfo.CurrentCulture, Localization.Strings.TradeOfferFailed, listedUser.SteamID, listedUser.Nickname));
 
 					break;
 				}
 
+				failuresInRow = 0;
+
 				Bot.ArchiLogger.LogGenericInfo(Strings.Success);
 
 				// Assume the trade offer has went through and was accepted, this will allow us to keep matching the same set with different users as if we've got what we wanted
@@ -921,10 +932,10 @@ internal sealed class RemoteCommunication : IAsyncDisposable, IDisposable {
 		}
 
 		if (pendingMobileTradeOfferIDs.Count > 0) {
-			(bool twoFactorSuccess, _, _) = await Bot.Actions.HandleTwoFactorAuthenticationConfirmations(true, Confirmation.EType.Trade, pendingMobileTradeOfferIDs, true).ConfigureAwait(false);
+			(bool twoFactorSuccess, IReadOnlyCollection<Confirmation>? handledConfirmations, _) = await Bot.Actions.HandleTwoFactorAuthenticationConfirmations(true, Confirmation.EType.Trade, pendingMobileTradeOfferIDs, true).ConfigureAwait(false);
 
 			if (!twoFactorSuccess) {
-				Bot.ArchiLogger.LogGenericWarning(string.Format(CultureInfo.CurrentCulture, Strings.WarningFailedWithError, nameof(twoFactorSuccess)));
+				Bot.ArchiLogger.LogGenericWarning(string.Format(CultureInfo.CurrentCulture, Localization.Strings.ActivelyMatchingSomeConfirmationsFailed, handledConfirmations?.Count ?? 0, pendingMobileTradeOfferIDs.Count));
 
 				return;
 			}