diff --git a/packages/insomnia-app/app/common/__tests__/validate-insomnia-config.test.ts b/packages/insomnia-app/app/common/__tests__/validate-insomnia-config.test.ts
index bdf45139db..a7c66ed20b 100644
--- a/packages/insomnia-app/app/common/__tests__/validate-insomnia-config.test.ts
+++ b/packages/insomnia-app/app/common/__tests__/validate-insomnia-config.test.ts
@@ -11,7 +11,26 @@ const electronShowErrorBox = mocked(electron.dialog.showErrorBox);
 const getConfigSettings = mocked(_getConfigSettings);
 
 describe('validateInsomniaConfig', () => {
-  it('should show error box and exit if there is an error', () => {
+  it('should show error box and exit if there is a parse error', () => {
+    // Arrange
+    const errorReturn = {
+      error: {
+        syntaxError: new SyntaxError('mock syntax error'),
+        fileContents: '{ "mock": ["insomnia", "config"] }',
+        configPath: '/mock/insomnia/config/path',
+      },
+    };
+    getConfigSettings.mockReturnValue(errorReturn);
+
+    // Act
+    validateInsomniaConfig();
+
+    // Assert
+    expect(electronShowErrorBox).toHaveBeenCalled();
+    expect(electronAppExit).toHaveBeenCalled();
+  });
+
+  it('should show error box and exit if there is a config error', () => {
     // Arrange
     const errorReturn = {
       error: {
diff --git a/packages/insomnia-app/app/common/validate-insomnia-config.ts b/packages/insomnia-app/app/common/validate-insomnia-config.ts
index dd6b8adb08..f66cac8417 100644
--- a/packages/insomnia-app/app/common/validate-insomnia-config.ts
+++ b/packages/insomnia-app/app/common/validate-insomnia-config.ts
@@ -1,27 +1,48 @@
 import electron from 'electron';
 
-import { getConfigSettings } from '../models/helpers/settings';
+import { getConfigSettings, isConfigError, isParseError } from '../models/helpers/settings';
 import { exitApp } from './electron-helpers';
 
 export const validateInsomniaConfig = () => {
   const configSettings = getConfigSettings();
-  if ('error' in configSettings) {
-    const errors = configSettings.error.humanReadableErrors?.map(({ message, path, suggestion }, index) => ([
+
+  if (!('error' in configSettings)) {
+    return;
+  }
+
+  if (isParseError(configSettings)) {
+    const { syntaxError, configPath } = configSettings.error;
+    electron.dialog.showErrorBox('Invalid Insomnia Config', [
+      'Failed to parse JSON file for Insomnia Config.',
+      '',
+      '[Path]',
+      configPath,
+      '',
+      '[Syntax Error]',
+      syntaxError.message,
+    ].join('\n'));
+  } else if (isConfigError(configSettings)) {
+    const { humanReadableErrors, configPath } = configSettings.error;
+    const errors = humanReadableErrors.map(({ message, path, suggestion }, index) => ([
       `[Error ${index + 1}]`,
       `Path: ${path}`,
       `${message}.${suggestion ? `  ${suggestion}` : ''}`,
     ]).join('\n')).join('\n\n');
 
-    electron.dialog.showErrorBox('Invalid Insomnia Config',
-      [
-        `Your Insomnia Config was found to be invalid.  Please check the path below for the following error${configSettings.error.humanReadableErrors?.length > 1 ? 's' : ''}:`,
-        '',
-        '[Path]',
-        configSettings.error.configPath,
-        '',
-        errors,
-      ].join('\n'),
+    electron.dialog.showErrorBox('Invalid Insomnia Config', [
+      `Your Insomnia Config was found to be invalid.  Please check the path below for the following error${configSettings.error.humanReadableErrors?.length > 1 ? 's' : ''}:`,
+      '',
+      '[Path]',
+      configPath,
+      '',
+      errors,
+    ].join('\n'));
+  } else {
+    electron.dialog.showErrorBox(
+      'An unexpected error occured while parsing Insomnia Config',
+      JSON.stringify(configSettings),
     );
-    exitApp();
   }
+
+  exitApp();
 };
diff --git a/packages/insomnia-app/app/models/helpers/settings.ts b/packages/insomnia-app/app/models/helpers/settings.ts
index 240ba3e291..9f61fc197b 100644
--- a/packages/insomnia-app/app/models/helpers/settings.ts
+++ b/packages/insomnia-app/app/models/helpers/settings.ts
@@ -9,27 +9,49 @@ import { ValueOf } from 'type-fest';
 import { isDevelopment } from '../../common/constants';
 import { getDataDirectory, getPortableExecutableDir } from '../../common/electron-helpers';
 
+interface FailedParseResult {
+  syntaxError: SyntaxError;
+  fileContents: string;
+  configPath: string;
+}
+
+const isFailedParseResult = (input: any): input is FailedParseResult => (
+  input ? input.syntaxError instanceof SyntaxError : false
+);
+
 /** takes an unresolved (or resolved will work fine too) filePath of the insomnia config and reads the insomniaConfig from disk */
-export const readConfigFile = (filePath?: string) => {
-  if (!filePath) {
+export const readConfigFile = (configPath?: string): unknown | FailedParseResult | undefined => {
+  if (!configPath) {
     return undefined;
   }
 
   let fileContents = '';
   try {
-    fileContents = readFileSync(filePath, 'utf-8');
+    fileContents = readFileSync(configPath, 'utf-8');
   } catch (error: unknown) {
+    // file not found
     return undefined;
   }
 
-  if (!fileContents) {
+  const fileIsFoundButEmpty = fileContents === '';
+  if (fileIsFoundButEmpty) {
     return undefined;
   }
 
   try {
     return JSON.parse(fileContents) as unknown;
-  } catch (error: unknown) {
-    console.error('failed to parse insomnia config', { filePath, fileContents }, error);
+  } catch (syntaxError: unknown) {
+    // note: all JSON.parse errors are SyntaxErrors
+    // see: https://developer.mozilla.org/en-US/docs/Web/JavaScript/Reference/Errors/JSON_bad_parse
+    if (syntaxError instanceof SyntaxError) {
+      console.error('failed to parse insomnia config', { configPath, fileContents, syntaxError });
+      const failedParseResult: FailedParseResult = {
+        syntaxError,
+        fileContents,
+        configPath: configPath,
+      };
+      return failedParseResult;
+    }
     return undefined;
   }
 };
@@ -55,10 +77,14 @@ export const getConfigFile = () => {
   // note: this is written as to avoid unnecessary (synchronous) reads from disk.
   // The paths above are in priority order such that if we already found what we're looking for, there's no reason to keep reading other files.
   for (const configPath of configPaths) {
-    const insomniaConfig = readConfigFile(configPath);
-    if (insomniaConfig !== undefined && configPath !== undefined) {
+    const fileReadResult = readConfigFile(configPath);
+    if (isFailedParseResult(fileReadResult)) {
+      return fileReadResult;
+    }
+
+    if (fileReadResult !== undefined && configPath !== undefined) {
       return {
-        insomniaConfig,
+        insomniaConfig: fileReadResult,
         configPath,
       };
     }
@@ -79,14 +105,33 @@ interface ConfigError {
   };
 }
 
+export const isConfigError = (input: any): input is ConfigError => (
+  input ? input.humanErrors?.length > 0 : false
+);
+
+interface ParseError {
+  error: FailedParseResult;
+}
+
+export const isParseError = (input: any): input is ParseError => (
+  input ? isFailedParseResult(input.error) : false
+);
+
 /**
  * gets settings from the `insomnia.config.json`
  *
  * note that it is a business rule that the config is never read again after startup, hence the `once` usage.
  */
-export const getConfigSettings: () => (NonNullable<InsomniaConfig['settings']> | ConfigError) = once(() => {
-  const { configPath, insomniaConfig } = getConfigFile();
+export const getConfigSettings: () => (NonNullable<InsomniaConfig['settings']> | ConfigError | ParseError) = once(() => {
+  const configFileResult = getConfigFile();
 
+  if (isFailedParseResult(configFileResult)) {
+    return {
+      error: configFileResult,
+    };
+  }
+
+  const { insomniaConfig, configPath } = configFileResult;
   const validationResult = validate(insomniaConfig as InsomniaConfig);
 
   if (isErrorResult(validationResult)) {