diff --git a/PluralKit.Bot/Bot.cs b/PluralKit.Bot/Bot.cs
index 2ce6232d..ec32a125 100644
--- a/PluralKit.Bot/Bot.cs
+++ b/PluralKit.Bot/Bot.cs
@@ -316,7 +316,15 @@ namespace PluralKit.Bot
                                           msg.Content.Substring(argPos).TrimStart().Length;
                 argPos += trimStartLengthDiff;
 
-                await _tree.ExecuteCommand(new Context(_services, msg, argPos, cachedAccount?.System));
+                try
+                {
+                    await _tree.ExecuteCommand(new Context(_services, msg, argPos, cachedAccount?.System));
+                }
+                catch (PKError)
+                {
+                    // Only permission errors will ever bubble this far and be caught here instead of Context.Execute
+                    // so we just catch and ignore these. TODO: this may need to change.
+                }
             }
             else if (cachedAccount != null)
             {
@@ -329,7 +337,8 @@ namespace PluralKit.Bot
                 }
                 catch (PKError e)
                 {
-                    await arg.Channel.SendMessageAsync($"{Emojis.Error} {e.Message}");
+                    if (arg.Channel.HasPermission(ChannelPermission.SendMessages))
+                        await arg.Channel.SendMessageAsync($"{Emojis.Error} {e.Message}");
                 }
             }
         }
@@ -343,7 +352,7 @@ namespace PluralKit.Bot
             // We'll fetch the event ID and send a user-facing error message.
             // ONLY IF this error's actually our problem. As for what defines an error as "our problem",
             // check the extension method :)
-            if (exc.IsOurProblem())
+            if (exc.IsOurProblem() && _msg.Channel.HasPermission(ChannelPermission.SendMessages))
             {
                 var eid = evt.EventId;
                 await _msg.Channel.SendMessageAsync(
diff --git a/PluralKit.Bot/CommandSystem/Context.cs b/PluralKit.Bot/CommandSystem/Context.cs
index cae120f6..77600daa 100644
--- a/PluralKit.Bot/CommandSystem/Context.cs
+++ b/PluralKit.Bot/CommandSystem/Context.cs
@@ -53,8 +53,17 @@ namespace PluralKit.Bot
         public bool HasNext(bool skipFlags = true) => RemainderOrNull(skipFlags) != null;
         public string FullCommand => _parameters.FullCommand;
 
-        public Task<IUserMessage> Reply(string text = null, Embed embed = null) =>
-            Channel.SendMessageAsync(text, embed: embed);
+        public Task<IUserMessage> Reply(string text = null, Embed embed = null)
+        {
+            if (!this.BotHasPermission(ChannelPermission.SendMessages))
+                // Will be "swallowed" during the error handler anyway, this message is never shown.
+                throw new PKError("PluralKit does not have permission to send messages in this channel.");
+
+            if (embed != null && !this.BotHasPermission(ChannelPermission.EmbedLinks))
+                throw new PKError("PluralKit does not have permission to send embeds in this channel. Please ensure I have the **Embed Links** permission enabled.");
+            
+            return Channel.SendMessageAsync(text, embed: embed);
+        }
 
         /// <summary>
         /// Checks if the next parameter is equal to one of the given keywords. Case-insensitive.
diff --git a/PluralKit.Bot/Utils/ContextUtils.cs b/PluralKit.Bot/Utils/ContextUtils.cs
index f104a645..ba411603 100644
--- a/PluralKit.Bot/Utils/ContextUtils.cs
+++ b/PluralKit.Bot/Utils/ContextUtils.cs
@@ -82,7 +82,7 @@ namespace PluralKit.Bot {
 
             try
             {
-                var msg = await ctx.Channel.SendMessageAsync(embed: await MakeEmbedForPage(0));
+                var msg = await ctx.Reply(embed: await MakeEmbedForPage(0));
                 if (pageCount == 1) return; // If we only have one page, don't bother with the reaction/pagination logic, lol
                 IEmote[] botEmojis = { new Emoji("\u23EA"), new Emoji("\u2B05"), new Emoji("\u27A1"), new Emoji("\u23E9"), new Emoji(Emojis.Error) };
                 await msg.AddReactionsAsync(botEmojis);
@@ -147,7 +147,7 @@ namespace PluralKit.Bot {
                 var pageCount = (items.Count-1) / pageSize + 1;
                 
                 // Send the original message
-                var msg = await ctx.Channel.SendMessageAsync($"**[Page {currPage + 1}/{pageCount}]**\n{description}\n{MakeOptionList(currPage)}");
+                var msg = await ctx.Reply($"**[Page {currPage + 1}/{pageCount}]**\n{description}\n{MakeOptionList(currPage)}");
                 
                 // Add back/forward reactions and the actual indicator emojis
                 async Task AddEmojis()
@@ -186,7 +186,7 @@ namespace PluralKit.Bot {
             }
             else
             {
-                var msg = await ctx.Channel.SendMessageAsync($"{description}\n{MakeOptionList(0)}");
+                var msg = await ctx.Reply($"{description}\n{MakeOptionList(0)}");
 
                 // Add the relevant reactions (we don't care too much about awaiting)
                 async Task AddEmojis()