diff --git a/src/handlers/shared/start.ts b/src/handlers/shared/start.ts
index d1e5a1c..8433e5b 100644
--- a/src/handlers/shared/start.ts
+++ b/src/handlers/shared/start.ts
@@ -18,7 +18,7 @@ export async function start(
   const { taskStaleTimeoutDuration } = config;
 
   if (!sender) {
-    throw new Error(logger.error(`Skipping '/start' since there is no sender in the context.`).logMessage.raw);
+    throw logger.error(`Skipping '/start' since there is no sender in the context.`);
   }
 
   // is it a child issue?
@@ -27,7 +27,7 @@ export async function start(
       context,
       "```diff\n# Please select a child issue from the specification checklist to work on. The '/start' command is disabled on parent issues.\n```"
     );
-    throw new Error(logger.error(`Skipping '/start' since the issue is a parent issue`).logMessage.raw);
+    throw logger.error(`Skipping '/start' since the issue is a parent issue`);
   }
 
   let commitHash: string | null = null;
@@ -46,7 +46,7 @@ export async function start(
   // is it assignable?
 
   if (issue.state === ISSUE_TYPE.CLOSED) {
-    throw new Error(logger.error("This issue is closed, please choose another.", { issueNumber: issue.number }).logMessage.raw);
+    throw logger.error("This issue is closed, please choose another.", { issueNumber: issue.number });
   }
 
   const assignees = issue?.assignees ?? [];
@@ -54,11 +54,9 @@ export async function start(
   // find out if the issue is already assigned
   if (assignees.length !== 0) {
     const isCurrentUserAssigned = !!assignees.find((assignee) => assignee?.login === sender.login);
-    throw new Error(
-      logger.error(
-        isCurrentUserAssigned ? "You are already assigned to this task." : "This issue is already assigned. Please choose another unassigned task.",
-        { issueNumber: issue.number }
-      ).logMessage.raw
+    throw logger.error(
+      isCurrentUserAssigned ? "You are already assigned to this task." : "This issue is already assigned. Please choose another unassigned task.",
+      { issueNumber: issue.number }
     );
   }
 
@@ -81,7 +79,7 @@ export async function start(
   }
 
   if (error) {
-    throw new Error(logger.error(error, { issueNumber: issue.number }).logMessage.raw);
+    throw logger.error(error, { issueNumber: issue.number });
   }
 
   // get labels
@@ -89,7 +87,7 @@ export async function start(
   const priceLabel = labels.find((label: Label) => label.name.startsWith("Price: "));
 
   if (!priceLabel) {
-    throw new Error(logger.error("No price label is set to calculate the duration", { issueNumber: issue.number }).logMessage.raw);
+    throw logger.error("No price label is set to calculate the duration", { issueNumber: issue.number });
   }
 
   const deadline = getDeadline(labels);
@@ -161,7 +159,7 @@ async function handleTaskLimitChecks(username: string, context: Context, logger:
   }
 
   if (await hasUserBeenUnassigned(context, username)) {
-    throw new Error(logger.error(`${username} you were previously unassigned from this task. You cannot be reassigned.`, { username }).logMessage.raw);
+    throw logger.error(`${username} you were previously unassigned from this task. You cannot be reassigned.`, { username });
   }
 
   return true;
diff --git a/src/handlers/shared/stop.ts b/src/handlers/shared/stop.ts
index af41cf6..9bd57ff 100644
--- a/src/handlers/shared/stop.ts
+++ b/src/handlers/shared/stop.ts
@@ -17,7 +17,7 @@ export async function stop(
   const userToUnassign = assignees.find((assignee: Partial<Assignee>) => assignee?.login?.toLowerCase() === sender.login.toLowerCase());
 
   if (!userToUnassign) {
-    throw new Error(logger.error("You are not assigned to this task", { issueNumber, user: sender.login })?.logMessage.raw as string);
+    throw logger.error("You are not assigned to this task", { issueNumber, user: sender.login });
   }
 
   // close PR
diff --git a/src/plugin.ts b/src/plugin.ts
index e027d4f..8369351 100644
--- a/src/plugin.ts
+++ b/src/plugin.ts
@@ -43,12 +43,10 @@ export async function startStopTask(inputs: PluginInputs, env: Env) {
     let errorMessage;
     if (err instanceof LogReturn) {
       errorMessage = err;
-    } else if (err instanceof Error) {
-      errorMessage = context.logger.error(err.message, { error: err });
+      await addCommentToIssue(context, `${errorMessage?.logMessage.diff}\n<!--\n${sanitizeMetadata(errorMessage?.metadata)}\n-->`);
     } else {
-      errorMessage = context.logger.error("An error occurred", { err });
+      context.logger.error("An error occurred", { err });
     }
-    await addCommentToIssue(context, `${errorMessage?.logMessage.diff}\n<!--\n${sanitizeMetadata(errorMessage?.metadata)}\n-->`);
   }
 }
 
diff --git a/src/utils/issue.ts b/src/utils/issue.ts
index adfc310..65a094e 100644
--- a/src/utils/issue.ts
+++ b/src/utils/issue.ts
@@ -1,4 +1,4 @@
-import type { RestEndpointMethodTypes } from "@octokit/plugin-rest-endpoint-methods/dist-types/generated/parameters-and-response-types";
+import { RestEndpointMethodTypes } from "@octokit/rest";
 import ms from "ms";
 import { Context } from "../types/context";
 import { GitHubIssueSearch, Review } from "../types/payload";
@@ -142,9 +142,7 @@ async function confirmMultiAssignment(context: Context, issueNumber: number, use
   });
 
   if (!assignees?.length) {
-    throw new Error(
-      logger.error("We detected that this task was not assigned to anyone. Please report this to the maintainers.", { issueNumber, usernames }).logMessage.raw
-    );
+    throw logger.error("We detected that this task was not assigned to anyone. Please report this to the maintainers.", { issueNumber, usernames });
   }
 
   if (isPrivate && assignees?.length <= 1) {
diff --git a/tests/main.test.ts b/tests/main.test.ts
index dec87fe..41e7e94 100644
--- a/tests/main.test.ts
+++ b/tests/main.test.ts
@@ -141,7 +141,7 @@ describe("User start/stop", () => {
 
     context.adapters = createAdapters(getSupabase(), context);
 
-    await expect(userStartStop(context)).rejects.toThrow("You are not assigned to this task");
+    await expect(userStartStop(context)).rejects.toMatchObject({ logMessage: { raw: "You are not assigned to this task" } });
   });
 
   test("User can't stop an issue without assignees", async () => {
@@ -151,7 +151,7 @@ describe("User start/stop", () => {
     const context = createContext(issue, sender, "/stop") as Context<"issue_comment.created">;
     context.adapters = createAdapters(getSupabase(), context as unknown as Context);
 
-    await expect(userStartStop(context)).rejects.toThrow("You are not assigned to this task");
+    await expect(userStartStop(context)).rejects.toMatchObject({ logMessage: { raw: "You are not assigned to this task" } });
   });
 
   test("User can't start an issue that's already assigned", async () => {
@@ -162,7 +162,9 @@ describe("User start/stop", () => {
 
     context.adapters = createAdapters(getSupabase(), context);
 
-    await expect(userStartStop(context)).rejects.toThrow("This issue is already assigned. Please choose another unassigned task.");
+    await expect(userStartStop(context)).rejects.toMatchObject({
+      logMessage: { raw: "This issue is already assigned. Please choose another unassigned task." },
+    });
   });
 
   test("User can't start an issue without a price label", async () => {
@@ -173,7 +175,7 @@ describe("User start/stop", () => {
 
     context.adapters = createAdapters(getSupabase(), context);
 
-    await expect(userStartStop(context)).rejects.toThrow("No price label is set to calculate the duration");
+    await expect(userStartStop(context)).rejects.toMatchObject({ logMessage: { raw: "No price label is set to calculate the duration" } });
   });
 
   test("User can't start an issue without a wallet address", async () => {
@@ -194,7 +196,7 @@ describe("User start/stop", () => {
 
     context.adapters = createAdapters(getSupabase(), context as unknown as Context);
 
-    await expect(userStartStop(context)).rejects.toThrow("This issue is closed, please choose another.");
+    await expect(userStartStop(context)).rejects.toMatchObject({ logMessage: { raw: "This issue is closed, please choose another." } });
   });
 
   test("User can't start an issue that's a parent issue", async () => {
@@ -205,7 +207,7 @@ describe("User start/stop", () => {
 
     context.adapters = createAdapters(getSupabase(), context);
 
-    await expect(userStartStop(context)).rejects.toThrow("Skipping '/start' since the issue is a parent issue");
+    await expect(userStartStop(context)).rejects.toMatchObject({ logMessage: { raw: "Skipping '/start' since the issue is a parent issue" } });
   });
 
   test("should set maxLimits to 6 if the user is a member", async () => {
@@ -218,7 +220,9 @@ describe("User start/stop", () => {
     const context = createContext(issue, sender) as unknown as Context;
 
     context.adapters = createAdapters(getSupabase(), context as unknown as Context);
-    await expect(userStartStop(context)).rejects.toThrow("You have reached your max task limit. Please close out some tasks before assigning new ones.");
+    await expect(userStartStop(context)).rejects.toMatchObject({
+      logMessage: { raw: "You have reached your max task limit. Please close out some tasks before assigning new ones." },
+    });
 
     expect(memberLimit).toEqual(6);
   });
@@ -230,7 +234,9 @@ describe("User start/stop", () => {
     const context = createContext(issue, sender, "/start") as Context<"issue_comment.created">;
     context.adapters = createAdapters(getSupabase(), context);
 
-    await expect(userStartStop(context)).rejects.toThrow("user2 you were previously unassigned from this task. You cannot be reassigned.");
+    await expect(userStartStop(context)).rejects.toMatchObject({
+      logMessage: { raw: "user2 you were previously unassigned from this task. You cannot be reassigned." },
+    });
   });
 
   test("Should throw if no BOT_USER_ID is set", async () => {