diff --git a/src/application/Parser/ApplicationParser.ts b/src/application/Parser/ApplicationParser.ts
index 612c5b9d..27c4c08e 100644
--- a/src/application/Parser/ApplicationParser.ts
+++ b/src/application/Parser/ApplicationParser.ts
@@ -31,7 +31,7 @@ function validateCollectionsData(
 ) {
   validator.assertNonEmptyCollection({
     value: collections,
-    valueName: 'collections',
+    valueName: 'Collections',
   });
 }
 
diff --git a/src/application/Parser/CategoryCollectionParser.ts b/src/application/Parser/CategoryCollectionParser.ts
index 7c92c7d3..be10a9d0 100644
--- a/src/application/Parser/CategoryCollectionParser.ts
+++ b/src/application/Parser/CategoryCollectionParser.ts
@@ -45,14 +45,14 @@ function validateCollection(
 ): void {
   validator.assertObject({
     value: content,
-    valueName: 'collection',
+    valueName: 'Collection',
     allowedProperties: [
       'os', 'scripting', 'actions', 'functions',
     ],
   });
   validator.assertNonEmptyCollection({
     value: content.actions,
-    valueName: '"actions" in collection',
+    valueName: '\'actions\' in collection',
   });
 }
 
diff --git a/src/application/Parser/Common/ContextualError.ts b/src/application/Parser/Common/ContextualError.ts
index fd00b655..5d4cb9c6 100644
--- a/src/application/Parser/Common/ContextualError.ts
+++ b/src/application/Parser/Common/ContextualError.ts
@@ -1,42 +1,116 @@
 import { CustomError } from '@/application/Common/CustomError';
+import { indentText } from '@/application/Common/Text/IndentText';
 
 export interface ErrorWithContextWrapper {
   (
-    error: Error,
+    innerError: Error,
     additionalContext: string,
   ): Error;
 }
 
 export const wrapErrorWithAdditionalContext: ErrorWithContextWrapper = (
-  error: Error,
-  additionalContext: string,
+  innerError,
+  additionalContext,
 ) => {
-  return (error instanceof ContextualError ? error : new ContextualError(error))
-    .withAdditionalContext(additionalContext);
+  if (!additionalContext) {
+    throw new Error('Missing additional context');
+  }
+  return new ContextualError({
+    innerError,
+    additionalContext,
+  });
 };
 
-/* AggregateError is similar but isn't well-serialized or displayed by browsers */
+/**
+ * Class for building a detailed error trace.
+ *
+ * Alternatives considered:
+ * - `AggregateError`:
+ *   Similar but not well-serialized or displayed by browsers such as Chromium (last tested v126).
+ * - `cause` property:
+ *   Not displayed by all browsers (last tested v126).
+ *   Reference: https://developer.mozilla.org/en-US/docs/Web/JavaScript/Reference/Global_Objects/Error/cause
+ *
+ * This is immutable where the constructor sets the values because using getter functions such as
+ * `get cause()`, `get message()` does not work on Chromium (last tested v126), but works fine on
+ * Firefox (last tested v127).
+ */
 class ContextualError extends CustomError {
-  private readonly additionalContext = new Array<string>();
+  constructor(public readonly context: ErrorContext) {
+    super(
+      generateDetailedErrorMessageWithContext(context),
+      {
+        cause: context.innerError,
+      },
+    );
+  }
+}
 
-  constructor(
-    public readonly innerError: Error,
-  ) {
-    super();
+interface ErrorContext {
+  readonly innerError: Error;
+  readonly additionalContext: string;
+}
+
+function generateDetailedErrorMessageWithContext(
+  context: ErrorContext,
+): string {
+  return [
+    '\n',
+    // Display the current error message first, then the root cause.
+    // This prevents repetitive main messages for errors with a `cause:` chain,
+    // aligning with browser error display conventions.
+    context.additionalContext,
+    '\n',
+    'Error Trace (starting from root cause):',
+    indentText(
+      formatErrorTrace(
+        // Displaying contexts from the top frame (deepest, most recent) aligns with
+        // common debugger/compiler standard.
+        extractErrorTraceAscendingFromDeepest(context),
+      ),
+    ),
+    '\n',
+  ].join('\n');
+}
+
+function extractErrorTraceAscendingFromDeepest(
+  context: ErrorContext,
+): string[] {
+  const originalError = findRootError(context.innerError);
+  const contextsDescendingFromMostRecent: string[] = [
+    context.additionalContext,
+    ...gatherContextsFromErrorChain(context.innerError),
+    originalError.toString(),
+  ];
+  const contextsAscendingFromDeepest = contextsDescendingFromMostRecent.reverse();
+  return contextsAscendingFromDeepest;
+}
+
+function findRootError(error: Error): Error {
+  if (error instanceof ContextualError) {
+    return findRootError(error.context.innerError);
   }
+  return error;
+}
 
-  public withAdditionalContext(additionalContext: string): this {
-    this.additionalContext.push(additionalContext);
-    return this;
+function gatherContextsFromErrorChain(
+  error: Error,
+  accumulatedContexts: string[] = [],
+): string[] {
+  if (error instanceof ContextualError) {
+    accumulatedContexts.push(error.context.additionalContext);
+    return gatherContextsFromErrorChain(error.context.innerError, accumulatedContexts);
   }
+  return accumulatedContexts;
+}
 
-  public get message(): string { // toString() is not used when Chromium logs it on console
-    return [
-      '\n',
-      this.innerError.message,
-      '\n',
-      'Additional context:',
-      ...this.additionalContext.map((context, index) => `${index + 1}: ${context}`),
-    ].join('\n');
+function formatErrorTrace(
+  errorMessages: readonly string[],
+): string {
+  if (errorMessages.length === 1) {
+    return errorMessages[0];
   }
+  return errorMessages
+    .map((context, index) => `${index + 1}.${indentText(context)}`)
+    .join('\n');
 }
diff --git a/src/application/Parser/Common/TypeValidator.ts b/src/application/Parser/Common/TypeValidator.ts
index 78f79cf5..eaefab54 100644
--- a/src/application/Parser/Common/TypeValidator.ts
+++ b/src/application/Parser/Common/TypeValidator.ts
@@ -108,7 +108,7 @@ function assertArray(
   valueName: string,
 ): asserts value is Array<unknown> {
   if (!isArray(value)) {
-    throw new Error(`'${valueName}' should be of type 'array', but is of type '${typeof value}'.`);
+    throw new Error(`${valueName} should be of type 'array', but is of type '${typeof value}'.`);
   }
 }
 
@@ -117,7 +117,7 @@ function assertString(
   valueName: string,
 ): asserts value is string {
   if (!isString(value)) {
-    throw new Error(`'${valueName}' should be of type 'string', but is of type '${typeof value}'.`);
+    throw new Error(`${valueName} should be of type 'string', but is of type '${typeof value}'.`);
   }
 }
 
diff --git a/src/application/Parser/Executable/CategoryParser.ts b/src/application/Parser/Executable/CategoryParser.ts
index 39d77e51..88d77a1b 100644
--- a/src/application/Parser/Executable/CategoryParser.ts
+++ b/src/application/Parser/Executable/CategoryParser.ts
@@ -84,7 +84,7 @@ function ensureValidCategory(
   });
   validator.assertType((v) => v.assertObject({
     value: category,
-    valueName: category.category ?? 'category',
+    valueName: `Category '${category.category}'` ?? 'Category',
     allowedProperties: [
       'docs', 'children', 'category',
     ],
diff --git a/src/application/Parser/Executable/Script/Compiler/Function/Call/Argument/FunctionCallArgument.ts b/src/application/Parser/Executable/Script/Compiler/Function/Call/Argument/FunctionCallArgument.ts
index 4483f51c..b53f5494 100644
--- a/src/application/Parser/Executable/Script/Compiler/Function/Call/Argument/FunctionCallArgument.ts
+++ b/src/application/Parser/Executable/Script/Compiler/Function/Call/Argument/FunctionCallArgument.ts
@@ -22,7 +22,7 @@ export const createFunctionCallArgument: FunctionCallArgumentFactory = (
   utilities.validateParameterName(parameterName);
   utilities.typeValidator.assertNonEmptyString({
     value: argumentValue,
-    valueName: `Missing argument value for the parameter "${parameterName}".`,
+    valueName: `Function parameter '${parameterName}'`,
   });
   return {
     parameterName,
diff --git a/src/application/Parser/Executable/Script/Compiler/Function/Call/FunctionCallsParser.ts b/src/application/Parser/Executable/Script/Compiler/Function/Call/FunctionCallsParser.ts
index d7dba7e3..94e56ee5 100644
--- a/src/application/Parser/Executable/Script/Compiler/Function/Call/FunctionCallsParser.ts
+++ b/src/application/Parser/Executable/Script/Compiler/Function/Call/FunctionCallsParser.ts
@@ -42,7 +42,7 @@ function getCallSequence(calls: FunctionCallsData, validator: TypeValidator): Fu
   if (isArray(calls)) {
     validator.assertNonEmptyCollection({
       value: calls,
-      valueName: 'function call sequence',
+      valueName: 'Function call sequence',
     });
     return calls as FunctionCallData[];
   }
@@ -56,7 +56,7 @@ function parseFunctionCall(
 ): FunctionCall {
   utilities.typeValidator.assertObject({
     value: call,
-    valueName: 'function call',
+    valueName: 'Function call',
     allowedProperties: ['function', 'parameters'],
   });
   const callArgs = parseArgs(call.parameters, utilities.createCallArgument);
diff --git a/src/application/Parser/Executable/Script/Compiler/Function/Shared/ParameterNameValidator.ts b/src/application/Parser/Executable/Script/Compiler/Function/Shared/ParameterNameValidator.ts
index 48a3a2f3..9577c7c6 100644
--- a/src/application/Parser/Executable/Script/Compiler/Function/Shared/ParameterNameValidator.ts
+++ b/src/application/Parser/Executable/Script/Compiler/Function/Shared/ParameterNameValidator.ts
@@ -13,7 +13,7 @@ export const validateParameterName = (
 ) => {
   typeValidator.assertNonEmptyString({
     value: parameterName,
-    valueName: 'parameter name',
+    valueName: 'Parameter name',
     rule: {
       expectedMatch: /^[0-9a-zA-Z]+$/,
       errorMessage: `parameter name must be alphanumeric but it was "${parameterName}".`,
diff --git a/src/application/Parser/Executable/Script/ScriptParser.ts b/src/application/Parser/Executable/Script/ScriptParser.ts
index 446227c5..d7be9d0c 100644
--- a/src/application/Parser/Executable/Script/ScriptParser.ts
+++ b/src/application/Parser/Executable/Script/ScriptParser.ts
@@ -102,7 +102,7 @@ function validateScript(
 ): asserts script is NonNullable<ScriptData> {
   validator.assertType((v) => v.assertObject<CallScriptData & CodeScriptData>({
     value: script,
-    valueName: script.name ?? 'script',
+    valueName: `Script '${script.name}'` ?? 'Script',
     allowedProperties: [
       'name', 'recommend', 'code', 'revertCode', 'call', 'docs',
     ],
diff --git a/src/application/Parser/ScriptingDefinition/ScriptingDefinitionParser.ts b/src/application/Parser/ScriptingDefinition/ScriptingDefinitionParser.ts
index baf065c1..83876990 100644
--- a/src/application/Parser/ScriptingDefinition/ScriptingDefinitionParser.ts
+++ b/src/application/Parser/ScriptingDefinition/ScriptingDefinitionParser.ts
@@ -37,7 +37,7 @@ function validateData(
 ): void {
   validator.assertObject({
     value: data,
-    valueName: 'scripting definition',
+    valueName: 'Scripting definition',
     allowedProperties: ['language', 'fileExtension', 'startCode', 'endCode'],
   });
 }
diff --git a/tests/unit/application/Parser/ApplicationParser.spec.ts b/tests/unit/application/Parser/ApplicationParser.spec.ts
index b5ad234e..b3cb15d3 100644
--- a/tests/unit/application/Parser/ApplicationParser.spec.ts
+++ b/tests/unit/application/Parser/ApplicationParser.spec.ts
@@ -134,7 +134,7 @@ describe('ApplicationParser', () => {
         const data = [new CollectionDataStub()];
         const expectedAssertion: NonEmptyCollectionAssertion = {
           value: data,
-          valueName: 'collections',
+          valueName: 'Collections',
         };
         const validator = new TypeValidatorStub();
         const sut = new ApplicationParserBuilder()
diff --git a/tests/unit/application/Parser/CategoryCollectionParser.spec.ts b/tests/unit/application/Parser/CategoryCollectionParser.spec.ts
index c58419e2..0b311704 100644
--- a/tests/unit/application/Parser/CategoryCollectionParser.spec.ts
+++ b/tests/unit/application/Parser/CategoryCollectionParser.spec.ts
@@ -28,7 +28,7 @@ describe('CategoryCollectionParser', () => {
       const data = new CollectionDataStub();
       const expectedAssertion: ObjectAssertion<CollectionData> = {
         value: data,
-        valueName: 'collection',
+        valueName: 'Collection',
         allowedProperties: [
           'os', 'scripting', 'actions', 'functions',
         ],
@@ -48,7 +48,7 @@ describe('CategoryCollectionParser', () => {
         const actions = [getCategoryStub('test1'), getCategoryStub('test2')];
         const expectedAssertion: NonEmptyCollectionAssertion = {
           value: actions,
-          valueName: '"actions" in collection',
+          valueName: '\'actions\' in collection',
         };
         const validator = new TypeValidatorStub();
         const context = new TestContext()
diff --git a/tests/unit/application/Parser/Common/ContextualError.spec.ts b/tests/unit/application/Parser/Common/ContextualError.spec.ts
index 3027b098..a4124f2a 100644
--- a/tests/unit/application/Parser/Common/ContextualError.spec.ts
+++ b/tests/unit/application/Parser/Common/ContextualError.spec.ts
@@ -1,101 +1,168 @@
 import { describe, it, expect } from 'vitest';
 import { CustomError } from '@/application/Common/CustomError';
 import { wrapErrorWithAdditionalContext } from '@/application/Parser/Common/ContextualError';
-import { splitTextIntoLines } from '@/application/Common/Text/SplitTextIntoLines';
+import { formatAssertionMessage } from '@tests/shared/FormatAssertionMessage';
+import { indentText } from '@/application/Common/Text/IndentText';
+import { itEachAbsentStringValue } from '@tests/unit/shared/TestCases/AbsentTests';
 
 describe('wrapErrorWithAdditionalContext', () => {
-  it('preserves the original error when wrapped', () => {
-    // arrange
-    const expectedError = new Error();
-    const context = new TestContext()
-      .withError(expectedError);
-    // act
-    const error = context.wrap();
-    // assert
-    const actualError = extractInnerErrorFromContextualError(error);
-    expect(actualError).to.equal(expectedError);
-  });
-  it('maintains the original error when re-wrapped', () => {
-    // arrange
-    const expectedError = new Error();
-
-    // act
-    const firstError = new TestContext()
-      .withError(expectedError)
-      .withAdditionalContext('first error')
-      .wrap();
-    const secondError = new TestContext()
-      .withError(firstError)
-      .withAdditionalContext('second error')
-      .wrap();
-
-    // assert
-    const actualError = extractInnerErrorFromContextualError(secondError);
-    expect(actualError).to.equal(expectedError);
-  });
-  it(`the object extends ${CustomError.name}`, () => {
+  it(`extend ${CustomError.name}`, () => {
     // arrange
     const expected = CustomError;
     // act
     const error = new TestContext()
-      .wrap();
+      .build();
     // assert
     expect(error).to.be.an.instanceof(expected);
   });
+  describe('inner error preservation', () => {
+    it('preserves the original error', () => {
+      // arrange
+      const expectedError = new Error();
+      const context = new TestContext()
+        .withInnerError(expectedError);
+      // act
+      const error = context.build();
+      // assert
+      const actualError = getInnerErrorFromContextualError(error);
+      expect(actualError).to.equal(expectedError);
+    });
+    it('sets the original error as the cause', () => {
+      // arrange
+      const expectedError = new Error('error causing the issue');
+      const context = new TestContext()
+        .withInnerError(expectedError);
+      // act
+      const error = context.build();
+      // assert
+      const actualError = error.cause;
+      expect(actualError).to.equal(expectedError);
+    });
+  });
   describe('error message construction', () => {
-    it('includes the message from the original error', () => {
+    it('includes the original error message', () => {
       // arrange
       const expectedOriginalErrorMessage = 'Message from the inner error';
 
       // act
       const error = new TestContext()
-        .withError(new Error(expectedOriginalErrorMessage))
-        .wrap();
+        .withInnerError(new Error(expectedOriginalErrorMessage))
+        .build();
 
       // assert
       expect(error.message).contains(expectedOriginalErrorMessage);
     });
-    it('appends provided additional context to the error message', () => {
+    it('includes original error toString() if message is absent', () => {
       // arrange
-      const expectedAdditionalContext = 'Expected additional context message';
+      const originalError = new Error();
+      const expectedPartInMessage = originalError.toString();
 
       // act
       const error = new TestContext()
-        .withAdditionalContext(expectedAdditionalContext)
-        .wrap();
+        .withInnerError(originalError)
+        .build();
 
       // assert
-      expect(error.message).contains(expectedAdditionalContext);
+      expect(error.message).contains(expectedPartInMessage);
     });
-    it('appends multiple contexts to the error message in sequential order', () => {
+    it('appends additional context to the error message', () => {
       // arrange
-      const expectedFirstContext = 'First context';
-      const expectedSecondContext = 'Second context';
+      const expectedAdditionalContext = 'Expected additional context message';
 
       // act
-      const firstError = new TestContext()
-        .withAdditionalContext(expectedFirstContext)
-        .wrap();
-      const secondError = new TestContext()
-        .withError(firstError)
-        .withAdditionalContext(expectedSecondContext)
-        .wrap();
+      const error = new TestContext()
+        .withAdditionalContext(expectedAdditionalContext)
+        .build();
 
       // assert
-      const messageLines = splitTextIntoLines(secondError.message);
-      expect(messageLines).to.contain(`1: ${expectedFirstContext}`);
-      expect(messageLines).to.contain(`2: ${expectedSecondContext}`);
+      expect(error.message).contains(expectedAdditionalContext);
+    });
+    describe('message order', () => {
+      it('displays the latest context before the original error message', () => {
+        // arrange
+        const originalErrorMessage = 'Original message from the inner error to be shown first';
+        const additionalContext = 'Context to be displayed after';
+
+        // act
+        const error = new TestContext()
+          .withInnerError(new Error(originalErrorMessage))
+          .withAdditionalContext(additionalContext)
+          .build();
+
+        // assert
+        expectMessageDisplayOrder(error.message, {
+          firstMessage: additionalContext,
+          secondMessage: originalErrorMessage,
+        });
+      });
+      it('appends multiple contexts from most specific to most general', () => {
+        // arrange
+        const deepErrorContext = 'first-context';
+        const parentErrorContext = 'second-context';
+
+        // act
+        const deepError = new TestContext()
+          .withAdditionalContext(deepErrorContext)
+          .build();
+        const parentError = new TestContext()
+          .withInnerError(deepError)
+          .withAdditionalContext(parentErrorContext)
+          .build();
+        const grandParentError = new TestContext()
+          .withInnerError(parentError)
+          .withAdditionalContext('latest-error')
+          .build();
+
+        // assert
+        expectMessageDisplayOrder(grandParentError.message, {
+          firstMessage: deepErrorContext,
+          secondMessage: parentErrorContext,
+        });
+      });
     });
   });
+  describe('throws error when context is missing', () => {
+    itEachAbsentStringValue((absentValue) => {
+      // arrange
+      const expectedError = 'Missing additional context';
+      const context = new TestContext()
+        .withAdditionalContext(absentValue);
+      // act
+      const act = () => context.build();
+      // assert
+      expect(act).to.throw(expectedError);
+    }, { excludeNull: true, excludeUndefined: true });
+  });
 });
 
+function expectMessageDisplayOrder(
+  actualMessage: string,
+  expectation: {
+    readonly firstMessage: string;
+    readonly secondMessage: string;
+  },
+): void {
+  const firstMessageIndex = actualMessage.indexOf(expectation.firstMessage);
+  const secondMessageIndex = actualMessage.indexOf(expectation.secondMessage);
+  expect(firstMessageIndex).to.be.lessThan(secondMessageIndex, formatAssertionMessage([
+    'Error output order does not match the expected order.',
+    'Expected the first message to be displayed before the second message.',
+    'Expected first message:',
+    indentText(expectation.firstMessage),
+    'Expected second message:',
+    indentText(expectation.secondMessage),
+    'Received message:',
+    indentText(actualMessage),
+  ]));
+}
+
 class TestContext {
-  private error: Error = new Error();
+  private innerError: Error = new Error(`[${TestContext.name}] original error`);
 
   private additionalContext = `[${TestContext.name}] additional context`;
 
-  public withError(error: Error) {
-    this.error = error;
+  public withInnerError(innerError: Error) {
+    this.innerError = innerError;
     return this;
   }
 
@@ -104,19 +171,21 @@ class TestContext {
     return this;
   }
 
-  public wrap(): ReturnType<typeof wrapErrorWithAdditionalContext> {
+  public build(): ReturnType<typeof wrapErrorWithAdditionalContext> {
     return wrapErrorWithAdditionalContext(
-      this.error,
+      this.innerError,
       this.additionalContext,
     );
   }
 }
 
-function extractInnerErrorFromContextualError(error: Error): Error {
-  const innerErrorProperty = 'innerError';
-  if (!(innerErrorProperty in error)) {
-    throw new Error(`${innerErrorProperty} property is missing`);
+function getInnerErrorFromContextualError(error: Error & {
+  readonly context?: {
+    readonly innerError?: Error;
+  },
+}): Error {
+  if (error?.context?.innerError instanceof Error) {
+    return error.context.innerError;
   }
-  const actualError = error[innerErrorProperty];
-  return actualError as Error;
+  throw new Error('Error must have a context with a valid innerError property.');
 }
diff --git a/tests/unit/application/Parser/Common/TypeValidator.spec.ts b/tests/unit/application/Parser/Common/TypeValidator.spec.ts
index 5bac11a2..410d55c9 100644
--- a/tests/unit/application/Parser/Common/TypeValidator.spec.ts
+++ b/tests/unit/application/Parser/Common/TypeValidator.spec.ts
@@ -217,7 +217,7 @@ describe('createTypeValidator', () => {
         }) => {
           it(description, () => {
             const valueName = 'invalidValue';
-            const expectedMessage = `'${valueName}' should be of type 'string', but is of type '${typeof invalidValue}'.`;
+            const expectedMessage = `${valueName} should be of type 'string', but is of type '${typeof invalidValue}'.`;
             const { assertNonEmptyString } = createTypeValidator();
             // act
             const act = () => assertNonEmptyString({ value: invalidValue, valueName });
diff --git a/tests/unit/application/Parser/Executable/Script/Compiler/Function/Call/FunctionCallsParser.spec.ts b/tests/unit/application/Parser/Executable/Script/Compiler/Function/Call/FunctionCallsParser.spec.ts
index 1a318ef4..720dc90e 100644
--- a/tests/unit/application/Parser/Executable/Script/Compiler/Function/Call/FunctionCallsParser.spec.ts
+++ b/tests/unit/application/Parser/Executable/Script/Compiler/Function/Call/FunctionCallsParser.spec.ts
@@ -57,7 +57,7 @@ describe('FunctionCallsParser', () => {
         const data = new FunctionCallDataStub();
         const expectedAssertion: ObjectAssertion<FunctionCallData> = {
           value: data,
-          valueName: 'function call',
+          valueName: 'Function call',
           allowedProperties: [
             'function', 'parameters',
           ],
@@ -117,7 +117,7 @@ describe('FunctionCallsParser', () => {
         const data: FunctionCallsData = [new FunctionCallDataStub()];
         const expectedAssertion: NonEmptyCollectionAssertion = {
           value: data,
-          valueName: 'function call sequence',
+          valueName: 'Function call sequence',
         };
         const validator = new TypeValidatorStub();
         const context = new TestContext()
@@ -134,7 +134,7 @@ describe('FunctionCallsParser', () => {
         const data: FunctionCallsData = [expectedValidatedCallData];
         const expectedAssertion: ObjectAssertion<FunctionCallData> = {
           value: expectedValidatedCallData,
-          valueName: 'function call',
+          valueName: 'Function call',
           allowedProperties: [
             'function', 'parameters',
           ],