diff --git a/src/client/pages/items/show.tsx b/src/client/pages/items/show.tsx
index 89843fd..3fd9d43 100644
--- a/src/client/pages/items/show.tsx
+++ b/src/client/pages/items/show.tsx
@@ -124,7 +124,7 @@ export const ItemsShow = () => {
                 <MaterialSymbol fill={true} css={exclamationIconStyle}>
                   error
                 </MaterialSymbol>
-                <div css={errorMessageBodyStyle}>{errorMessage}</div>
+                <div>{errorMessage}</div>
               </p>
             ))}
           </div>
@@ -184,7 +184,3 @@ const errorStyle = css({
   display: "flex",
   marginTop: getSpace(3 / 2),
 });
-
-const errorMessageBodyStyle = css({
-  whiteSpace: "pre",
-});
diff --git a/src/commands/index.ts b/src/commands/index.ts
index 572baa3..b6d4074 100644
--- a/src/commands/index.ts
+++ b/src/commands/index.ts
@@ -1,3 +1,4 @@
+import { handleError } from "../lib/error-handler";
 import { packageUpdateNotice } from "../lib/package-update-notice";
 import { help, helpText } from "./help";
 import { init } from "./init";
@@ -38,5 +39,11 @@ export const exec = async (commandName: string, commandArgs: string[]) => {
     console.log(updateMessage);
   }
 
-  commands[commandName](commandArgs);
+  try {
+    await commands[commandName](commandArgs);
+  } catch (err) {
+    console.error(err);
+    await handleError(err as Error);
+    process.exit(1);
+  }
 };
diff --git a/src/commands/publish.ts b/src/commands/publish.ts
index 91b29fa..2b0e9fa 100644
--- a/src/commands/publish.ts
+++ b/src/commands/publish.ts
@@ -65,10 +65,15 @@ export const publish = async (argv: string[]) => {
     return acc;
   }, [] as { name: string; errors: string[] }[]);
   if (invalidItemMessages.length > 0) {
-    console.error("Validation error:");
+    const chalk = (await import("chalk")).default;
     invalidItemMessages.forEach((msg) => {
-      console.error(msg.name, msg.errors);
+      msg.errors.forEach((err) => {
+        const errorName = chalk.red.bold(msg.name + ":");
+        const errorDescription = chalk.red(err);
+        console.error(`${errorName} ${errorDescription}`);
+      });
     });
+
     process.exit(1);
   }
 
diff --git a/src/lib/check-frontmatter-type.ts b/src/lib/check-frontmatter-type.ts
index 2f98e39..00d077f 100644
--- a/src/lib/check-frontmatter-type.ts
+++ b/src/lib/check-frontmatter-type.ts
@@ -65,7 +65,7 @@ const checkOrganizationUrlName: CheckType = {
 
 const checkSlide: CheckType = {
   getMessage: () =>
-    "slideの設定はtrue/falseで入力してください\n\n【破壊的な変更がありました】\n詳しくは以下のリリースをご確認ください\nhttps://github.com/increments/qiita-cli/releases/tag/v0.5.0",
+    "slideの設定はtrue/falseで入力してください（破壊的な変更がありました。詳しくはリリースをご確認ください https://github.com/increments/qiita-cli/releases/tag/v0.5.0）",
   isValid: ({ slide }) => {
     return typeof slide === "boolean";
   },
diff --git a/src/lib/error-handler.ts b/src/lib/error-handler.ts
new file mode 100644
index 0000000..a3939ac
--- /dev/null
+++ b/src/lib/error-handler.ts
@@ -0,0 +1,86 @@
+import {
+  QiitaBadRequestError,
+  QiitaFetchError,
+  QiitaForbiddenError,
+  QiitaInternalServerError,
+  QiitaNotFoundError,
+  QiitaRateLimitError,
+  QiitaUnauthorizedError,
+  QiitaUnknownError,
+} from "../qiita-api";
+
+export const handleError = async (error: Error) => {
+  const chalk = (await import("chalk")).default;
+
+  switch (error.name) {
+    // Qiita API
+    case QiitaFetchError.name:
+      console.error(
+        chalk.red.bold(
+          "Qiita APIへのリクエストでネットワークエラーが発生しました"
+        )
+      );
+      console.error(
+        chalk.red("  インターネットに接続されているかご確認ください")
+      );
+      break;
+    case QiitaBadRequestError.name:
+      console.error(chalk.red.bold("Qiita APIへのリクエストに失敗しました"));
+      console.error(chalk.red("  記事ファイルに不備がないかご確認ください"));
+      break;
+    case QiitaUnauthorizedError.name:
+      console.error(chalk.red.bold("Qiitaの認証に失敗しました"));
+      console.error(
+        chalk.red("  loginコマンドでQiitaにログインしているかご確認ください")
+      );
+      console.error(
+        chalk.red("  Qiitaのアクセストークンが正しいかご確認ください")
+      );
+      break;
+    case QiitaForbiddenError.name:
+      console.error(chalk.red.bold("Qiita APIへのリクエストに失敗しました"));
+      console.error(
+        chalk.red("  Qiitaのアクセストークンが正しいかご確認ください")
+      );
+      console.error(chalk.red(""));
+      break;
+    case QiitaNotFoundError.name:
+      console.error(chalk.red.bold("記事が見つかりませんでした"));
+      console.error(
+        chalk.red("  Qiita上で記事が削除されていないかご確認ください")
+      );
+      break;
+    case QiitaRateLimitError.name:
+      console.error(chalk.red.bold("Qiita APIのレートリミットに達しました"));
+      console.error(chalk.red("  しばらく時間を置いてから再度お試しください"));
+      break;
+    case QiitaInternalServerError.name:
+      console.error(chalk.red.bold("Qiitaのサーバーでエラーが発生しました"));
+      console.error(chalk.red("  しばらく時間を置いてから再度お試しください"));
+      break;
+    case QiitaUnknownError.name:
+      console.error(
+        chalk.red.bold("Qiita APIへのリクエストで不明なエラーが発生しました")
+      );
+      console.error(
+        chalk.red(
+          "  バグの可能性がある場合は、Qiita Discussionsよりご報告いただけると幸いです"
+        )
+      );
+      console.error(
+        chalk.red("  https://github.com/increments/qiita-discussions")
+      );
+      break;
+
+    default:
+      console.error(chalk.red.bold(`エラーが発生しました (${error.message})`));
+      console.error(
+        chalk.red(
+          "  バグの可能性がある場合は、Qiita Discussionsよりご報告いただけると幸いです"
+        )
+      );
+      console.error(
+        chalk.red("  https://github.com/increments/qiita-discussions")
+      );
+  }
+};
diff --git a/src/qiita-api/errors.ts b/src/qiita-api/errors.ts
new file mode 100644
index 0000000..f925eaa
--- /dev/null
+++ b/src/qiita-api/errors.ts
@@ -0,0 +1,55 @@
+export class QiitaFetchError extends Error {
+  constructor(message: string) {
+    super(message);
+    this.name = "QiitaFetchError";
+  }
+}
+
+export class QiitaBadRequestError extends Error {
+  constructor(message: string) {
+    super(message);
+    this.name = "QiitaBadRequestError";
+  }
+}
+
+export class QiitaUnauthorizedError extends Error {
+  constructor(message: string) {
+    super(message);
+    this.name = "QiitaUnauthorizedError";
+  }
+}
+
+export class QiitaForbiddenError extends Error {
+  constructor(message: string) {
+    super(message);
+    this.name = "QiitaForbiddenError";
+  }
+}
+
+export class QiitaNotFoundError extends Error {
+  constructor(message: string) {
+    super(message);
+    this.name = "QiitaNotFoundError";
+  }
+}
+
+export class QiitaRateLimitError extends Error {
+  constructor(message: string) {
+    super(message);
+    this.name = "QiitaRateLimitError";
+  }
+}
+
+export class QiitaInternalServerError extends Error {
+  constructor(message: string) {
+    super(message);
+    this.name = "QiitaInternalServerError";
+  }
+}
+
+export class QiitaUnknownError extends Error {
+  constructor(message: string) {
+    super(message);
+    this.name = "QiitaUnknownError";
+  }
+}
diff --git a/src/qiita-api/index.ts b/src/qiita-api/index.ts
index 7571661..655e9ee 100644
--- a/src/qiita-api/index.ts
+++ b/src/qiita-api/index.ts
@@ -1,6 +1,18 @@
 import { URL, URLSearchParams } from "node:url";
+import {
+  QiitaBadRequestError,
+  QiitaFetchError,
+  QiitaForbiddenError,
+  QiitaInternalServerError,
+  QiitaNotFoundError,
+  QiitaRateLimitError,
+  QiitaUnauthorizedError,
+  QiitaUnknownError,
+} from "./errors";
 import { qiitaApiDebugger } from "./lib/debugger";
 
+export * from "./errors";
+
 export interface Item {
   body: string;
   id: string;
@@ -65,7 +77,7 @@ export class QiitaApi {
       });
     } catch (err) {
       console.error(err);
-      throw new Error("NetworkError");
+      throw new QiitaFetchError((err as Error).message);
     }
 
     if (response.ok) {
@@ -78,8 +90,8 @@ export class QiitaApi {
       }
     }
 
+    const responseBody = await response.text();
     if (qiitaApiDebugger.enabled) {
-      const responseBody = await response.text();
       qiitaApiDebugger(
         "request failed",
         JSON.stringify({
@@ -89,21 +101,22 @@ export class QiitaApi {
       );
     }
 
+    const errorMessage = responseBody.slice(0, 100);
     switch (response.status) {
       case 400:
-        throw new Error("QiitaBadRequestError");
+        throw new QiitaBadRequestError(errorMessage);
       case 401:
-        throw new Error("QiitaUnauthorizedError");
+        throw new QiitaUnauthorizedError(errorMessage);
       case 403:
-        throw new Error("QiitaForbiddenError");
+        throw new QiitaForbiddenError(errorMessage);
       case 404:
-        throw new Error("QiitaNotFoundError");
+        throw new QiitaNotFoundError(errorMessage);
       case 429:
-        throw new Error("QiitaRateLimitError");
+        throw new QiitaRateLimitError(errorMessage);
       case 500:
-        throw new Error("QiitaInternalServerError");
+        throw new QiitaInternalServerError(errorMessage);
       default:
-        throw new Error("QiitaUnknownError");
+        throw new QiitaUnknownError(errorMessage);
     }
   }
 
diff --git a/src/server/app.ts b/src/server/app.ts
index 4d97fd1..9f2de35 100644
--- a/src/server/app.ts
+++ b/src/server/app.ts
@@ -35,7 +35,7 @@ export async function startServer() {
   const port = userConfig.port;
   const host = "localhost";
 
-  return new Promise<Server>((resolve) => {
+  return new Promise<Server>((resolve, reject) => {
     server
       .listen(port, host)
       .once("listening", () => {
@@ -43,8 +43,8 @@ export async function startServer() {
 
         resolve(server);
       })
-      .once("error", () => {
-        throw new Error("Failed to start server");
+      .once("error", (err) => {
+        reject(err);
       });
   });
 }