diff --git a/Myriad/Rest/DiscordApiClient.cs b/Myriad/Rest/DiscordApiClient.cs
index 38ff3635..347b7352 100644
--- a/Myriad/Rest/DiscordApiClient.cs
+++ b/Myriad/Rest/DiscordApiClient.cs
@@ -47,6 +47,15 @@ public class DiscordApiClient
         _client.Get<GuildMember>($"/guilds/{guildId}/members/{userId}",
             ("GetGuildMember", guildId));
 
+    public Task<Message[]> GetChannelMessages(ulong channelId, int? limit)
+    {
+        var url = $"/channels/{channelId}/messages";
+        if (limit != null)
+            url += $"?limit={limit}";
+
+        return _client.Get<Message[]>(url, ("GetChannelMessages", channelId))!;
+    }
+
     public Task<Message> CreateMessage(ulong channelId, MessageRequest request, MultipartFile[]? files = null) =>
         _client.PostMultipart<Message>($"/channels/{channelId}/messages", ("CreateMessage", channelId), request,
             files)!;
diff --git a/PluralKit.Bot/Commands/Message.cs b/PluralKit.Bot/Commands/Message.cs
index 49384356..5c1c4b42 100644
--- a/PluralKit.Bot/Commands/Message.cs
+++ b/PluralKit.Bot/Commands/Message.cs
@@ -157,7 +157,13 @@ public class ProxiedMessage
             if (ctx.Guild == null)
                 throw new PKSyntaxError($"You must use a message link to {editType} messages in DMs.");
 
-            var recent = await FindRecentMessage(ctx, timeout);
+            PKMessage? recent;
+
+            if (isReproxy)
+                recent = await ctx.Repository.GetLastMessage(ctx.Guild.Id, ctx.Channel.Id, ctx.Author.Id);
+            else
+                recent = await FindRecentMessage(ctx, timeout);
+
             if (recent == null)
                 throw new PKSyntaxError($"Could not find a recent message to {editType}.");
 
@@ -182,9 +188,15 @@ public class ProxiedMessage
                 throw new PKError(error);
         }
 
+        var latestMessages = await _rest.GetChannelMessages(msg.Message.Channel, 2);
+        var isLatestMessage = latestMessages.LastOrDefault()?.Id == ctx.Message.Id
+            ? latestMessages.FirstOrDefault()?.Id == msg.Message.Mid
+            : latestMessages.LastOrDefault()?.Id == msg.Message.Mid;
+
         var msgTimestamp = DiscordUtils.SnowflakeToInstant(msg.Message.Mid);
-        if (isReproxy && SystemClock.Instance.GetCurrentInstant() - msgTimestamp > timeout)
-            throw new PKError($"The message is too old to be {editTypeAction}.");
+        if (isReproxy && !isLatestMessage)
+            if (SystemClock.Instance.GetCurrentInstant() - msgTimestamp > timeout)
+                throw new PKError($"The message is too old to be {editTypeAction}.");
 
         return msg;
     }