diff --git a/src/commands/CommandHandler.ts b/src/commands/CommandHandler.ts
index df39c90c..f2212db3 100644
--- a/src/commands/CommandHandler.ts
+++ b/src/commands/CommandHandler.ts
@@ -48,7 +48,7 @@ import { BaseFunction, CommandTable, defineCommandTable, findCommandTable, findT
 import { findMatrixInterfaceAdaptor, MatrixContext } from "./interface-manager/MatrixInterfaceAdaptor";
 import { ArgumentStream } from "./interface-manager/ParameterParsing";
 import { CommandResult } from "./interface-manager/Validation";
-import { CommandException } from "./interface-manager/CommandException";
+import { CommandException, CommandExceptionKind } from "./interface-manager/CommandException";
 import { tickCrossRenderer } from "./interface-manager/MatrixHelpRenderer";
 import "./interface-manager/MatrixPresentations";
 
@@ -133,7 +133,7 @@ export async function handleCommand(roomId: string, event: { content: { body: st
             try {
                 return await adaptor.invoke(mjolnirContext, mjolnirContext, ...stream.rest());
             } catch (e) {
-                const commandError = new CommandException(e, 'Unknown Unexpected Error');
+                const commandError = new CommandException(CommandExceptionKind.Unknown, e, 'Unknown Unexpected Error');
                 await tickCrossRenderer.call(mjolnirContext, mjolnir.client, roomId, event, CommandResult.Err(commandError));
             }
         }
diff --git a/src/commands/Rooms.tsx b/src/commands/Rooms.tsx
index d5cd70a2..eaf80613 100644
--- a/src/commands/Rooms.tsx
+++ b/src/commands/Rooms.tsx
@@ -30,7 +30,7 @@ import { findPresentationType, parameters } from "./interface-manager/ParameterP
 import { MjolnirContext } from "./CommandHandler";
 import { MatrixRoomID, MatrixRoomReference } from "./interface-manager/MatrixRoomReference";
 import { CommandResult } from "./interface-manager/Validation";
-import { CommandException } from "./interface-manager/CommandException";
+import { CommandException, CommandExceptionKind } from "./interface-manager/CommandException";
 import { defineMatrixInterfaceAdaptor } from "./interface-manager/MatrixInterfaceAdaptor";
 import { tickCrossRenderer } from "./interface-manager/MatrixHelpRenderer";
 import { DocumentNode } from "./interface-manager/DeadDocument";
@@ -92,7 +92,7 @@ defineInterfaceCommand({
                 return CommandException.Result<MatrixRoomID>(
                     `The homeserver that Draupnir is hosted on cannot join this room using the room reference provided.\
                     Try an alias or the "share room" button in your client to obtain a valid reference to the room.`,
-                    { exception: e }
+                    { exception: e, exceptionKind: CommandExceptionKind.Unknown }
                 );
             }
         })();
@@ -121,7 +121,10 @@ defineInterfaceCommand({
         try {
             await this.mjolnir.client.leaveRoom(roomID.toRoomIdOrAlias());
         } catch (exception) {
-            return CommandException.Result(`Failed to leave ${roomRef.toPermalink()} - the room is no longer being protected, but the bot could not leave.`, { exception });
+            return CommandException.Result(
+                `Failed to leave ${roomRef.toPermalink()} - the room is no longer being protected, but the bot could not leave.`,
+                { exceptionKind: CommandExceptionKind.Unknown, exception }
+            );
         }
         return CommandResult.Ok(undefined);
     },
diff --git a/src/commands/interface-manager/CommandException.ts b/src/commands/interface-manager/CommandException.ts
index ba8ee132..2dfa8ec2 100644
--- a/src/commands/interface-manager/CommandException.ts
+++ b/src/commands/interface-manager/CommandException.ts
@@ -5,6 +5,22 @@
 
 import { randomUUID } from "crypto";
 import { CommandError, CommandResult } from "./Validation";
+import { LogService } from "matrix-bot-sdk";
+
+export enum CommandExceptionKind {
+    /**
+     * This class is for exceptions that need to be reported to the user,
+     * but are mostly irrelevant to the developers because the behaviour is well
+     * understood and expected. These exceptions will never be logged to the error
+     * level.
+     */
+    Known = 'Known',
+    /**
+     * This class is to be used for reporting unexpected or unknown exceptions
+     * that the developers need to know about.
+     */
+    Unknown = 'Unknown',
+}
 
 // FIXME: I wonder if we could allow message to be JSX?
 //        Then room references could be put into the DM and actually mean something.
@@ -12,12 +28,22 @@ export class CommandException extends CommandError {
     public readonly uuid = randomUUID();
 
     constructor(
+        public readonly exceptionKind: CommandExceptionKind,
         public readonly exception: Error|unknown,
         message: string) {
         super(message)
     }
 
-    public static Result<Ok>(message: string, options: { exception: Error }): CommandResult<Ok, CommandException> {
-        return CommandResult.Err(new CommandException(options.exception, message));
+    public static Result<Ok>(message: string, options: { exception: Error, exceptionKind: CommandExceptionKind }): CommandResult<Ok, CommandException> {
+        return CommandResult.Err(new CommandException(options.exceptionKind, options.exception, message));
+    }
+
+    protected log(): void {
+        const logArguments: Parameters<typeof LogService['info']> = ["CommandException", this.exceptionKind, this.uuid, this.message, this.exception];
+        if (this.exceptionKind === CommandExceptionKind.Known) {
+            LogService.info(...logArguments);
+        } else {
+            LogService.error(...logArguments);
+        }
     }
 }
diff --git a/src/commands/interface-manager/Validation.ts b/src/commands/interface-manager/Validation.ts
index 7ee60a31..65582ab6 100644
--- a/src/commands/interface-manager/Validation.ts
+++ b/src/commands/interface-manager/Validation.ts
@@ -24,6 +24,7 @@ limitations under the License.
  * However, this file is modified and the modifications in this file
  * are NOT distributed, contributed, committed, or licensed under the Apache License.
  */
+import { LogService } from "matrix-bot-sdk";
 
 type ValidationMatchExpression<Ok, Err> = { ok?: (ok: Ok) => any, err?: (err: Err) => any};
 
@@ -89,7 +90,7 @@ export class CommandError {
     public constructor(
         public readonly message: string,
     ) {
-
+        this.log();
     }
 
     /**
@@ -101,4 +102,8 @@ export class CommandError {
     public static Result<Ok>(message: string, _options = {}): CommandResult<Ok> {
         return CommandResult.Err(new CommandError(message));
     }
+
+    protected log(): void {
+        LogService.info("CommandError", this.message);
+    }
 }