diff --git a/packages/schematics/angular/refactor/jasmine-vitest/test-file-transformer.integration_spec.ts b/packages/schematics/angular/refactor/jasmine-vitest/test-file-transformer.integration_spec.ts
index 5b30e9f24f4b..ce667dce1afc 100644
--- a/packages/schematics/angular/refactor/jasmine-vitest/test-file-transformer.integration_spec.ts
+++ b/packages/schematics/angular/refactor/jasmine-vitest/test-file-transformer.integration_spec.ts
@@ -392,14 +392,14 @@ describe('Jasmine to Vitest Transformer - Integration Tests', () => {
 
         it('should handle fail()', () => {
           if (true) {
-            throw new Error('This should not have happened');
+            expect.fail('This should not have happened');
           }
         });
 
         it('should handle fail() with a specific error', () => {
           try {
             expect(1).toBe(2);
-            throw new Error('Expected test to fail');
+            expect.fail('Expected test to fail');
           } catch (err) {
             expect(err.message).toBe('1 !== 2');
           }
diff --git a/packages/schematics/angular/refactor/jasmine-vitest/test-file-transformer.ts b/packages/schematics/angular/refactor/jasmine-vitest/test-file-transformer.ts
index f652368b03f7..e436434f134a 100644
--- a/packages/schematics/angular/refactor/jasmine-vitest/test-file-transformer.ts
+++ b/packages/schematics/angular/refactor/jasmine-vitest/test-file-transformer.ts
@@ -144,6 +144,7 @@ const callExpressionTransformers = [
 
   // **Stage 3: Global Functions & Cleanup**
   // These handle global Jasmine functions and catch-alls for unsupported APIs.
+  transformFail,
   transformTimerMocks,
   transformUnsupportedGlobalFunctions,
   transformUnsupportedJasmineCalls,
@@ -168,7 +169,6 @@ const expressionStatementTransformers = [
   transformCalledOnceWith,
   transformArrayWithExactContents,
   transformExpectNothing,
-  transformFail,
   transformJasmineMembers,
 ];
 
@@ -227,18 +227,16 @@ export function transformJasmineToVitest(
         }
 
         for (const transformer of callExpressionTransformers) {
-          if (
-            !(
-              (options.browserMode && transformer === transformToHaveClass) ||
-              (options.fakeAsync === false &&
-                [
-                  transformFakeAsyncFlush,
-                  transformFakeAsyncFlushMicrotasks,
-                  transformFakeAsyncTick,
-                  transformFakeAsyncTest,
-                ].includes(transformer))
-            )
-          ) {
+          if (!(
+            (options.browserMode && transformer === transformToHaveClass) ||
+            (options.fakeAsync === false &&
+              [
+                transformFakeAsyncFlush,
+                transformFakeAsyncFlushMicrotasks,
+                transformFakeAsyncTick,
+                transformFakeAsyncTest,
+              ].includes(transformer))
+          )) {
             transformedNode = transformer(transformedNode, refactorCtx);
           }
         }
diff --git a/packages/schematics/angular/refactor/jasmine-vitest/test-file-transformer_add-imports_spec.ts b/packages/schematics/angular/refactor/jasmine-vitest/test-file-transformer_add-imports_spec.ts
index f4b10d485920..cbe05226ef7b 100644
--- a/packages/schematics/angular/refactor/jasmine-vitest/test-file-transformer_add-imports_spec.ts
+++ b/packages/schematics/angular/refactor/jasmine-vitest/test-file-transformer_add-imports_spec.ts
@@ -178,4 +178,24 @@ describe('Jasmine to Vitest Transformer - addImports option', () => {
       `;
     await expectTransformation(input, expected, true);
   });
+
+  it('should add import for `expect` when `fail()` is used and addImports is true', async () => {
+    const input = `
+        describe('My Suite', () => {
+          it('fails', () => {
+            fail('Something went wrong');
+          });
+        });
+      `;
+    const expected = `
+        import { describe, expect, it } from 'vitest';
+
+        describe('My Suite', () => {
+          it('fails', () => {
+            expect.fail('Something went wrong');
+          });
+        });
+      `;
+    await expectTransformation(input, expected, true);
+  });
 });
diff --git a/packages/schematics/angular/refactor/jasmine-vitest/transformers/jasmine-misc.ts b/packages/schematics/angular/refactor/jasmine-vitest/transformers/jasmine-misc.ts
index f71353cc9783..fe7e944e53e1 100644
--- a/packages/schematics/angular/refactor/jasmine-vitest/transformers/jasmine-misc.ts
+++ b/packages/schematics/angular/refactor/jasmine-vitest/transformers/jasmine-misc.ts
@@ -90,29 +90,53 @@ export function transformTimerMocks(node: ts.Node, ctx: RefactorContext): ts.Nod
   return node;
 }
 
-export function transformFail(node: ts.Node, { sourceFile, reporter }: RefactorContext): ts.Node {
+export function transformFail(
+  node: ts.Node,
+  { sourceFile, reporter, pendingVitestValueImports }: RefactorContext,
+): ts.Node {
   if (
-    ts.isExpressionStatement(node) &&
-    ts.isCallExpression(node.expression) &&
-    ts.isIdentifier(node.expression.expression) &&
-    node.expression.expression.text === 'fail'
+    ts.isCallExpression(node) &&
+    ts.isIdentifier(node.expression) &&
+    node.expression.text === 'fail'
   ) {
-    reporter.reportTransformation(sourceFile, node, 'Transformed `fail()` to `throw new Error()`.');
-
-    const arg = node.expression.arguments[0];
-    let throwExpression: ts.Expression;
-
-    if (arg && ts.isNewExpression(arg)) {
-      throwExpression = arg;
-    } else {
-      throwExpression = ts.factory.createNewExpression(
-        ts.factory.createIdentifier('Error'),
-        undefined,
-        arg ? [arg] : [],
-      );
+    addVitestValueImport(pendingVitestValueImports, 'expect');
+    reporter.reportTransformation(sourceFile, node, 'Transformed `fail()` to `expect.fail()`.');
+
+    const arg = node.arguments[0];
+    let replacementArg: ts.Expression | undefined = arg;
+    let hasNonStringArg = false;
+
+    if (arg) {
+      if (ts.isNewExpression(arg)) {
+        replacementArg = arg.arguments && arg.arguments.length > 0 ? arg.arguments[0] : undefined;
+      } else if (
+        !ts.isStringLiteral(arg) &&
+        !ts.isNoSubstitutionTemplateLiteral(arg) &&
+        !ts.isTemplateExpression(arg)
+      ) {
+        replacementArg = ts.factory.createCallExpression(
+          ts.factory.createIdentifier('String'),
+          undefined,
+          [arg],
+        );
+        hasNonStringArg = true;
+      }
     }
 
-    const replacement = ts.factory.createThrowStatement(throwExpression);
+    const replacement = ts.factory.createCallExpression(
+      ts.factory.createPropertyAccessExpression(
+        ts.factory.createIdentifier('expect'),
+        ts.factory.createIdentifier('fail'),
+      ),
+      undefined,
+      replacementArg ? [replacementArg] : [],
+    );
+
+    if (hasNonStringArg) {
+      const category = 'fail-non-string-argument';
+      reporter.recordTodo(category, sourceFile, node);
+      addTodoComment(replacement, category);
+    }
 
     return ts.setOriginalNode(ts.setTextRange(replacement, node), node);
   }
@@ -197,11 +221,7 @@ const UNSUPPORTED_GLOBAL_FUNCTION_CATEGORIES = new Set<TodoCategory>([
 function isUnsupportedGlobalFunction(
   methodName: string,
 ): methodName is
-  | 'setSpecProperty'
-  | 'setSuiteProperty'
-  | 'throwUnless'
-  | 'throwUnlessAsync'
-  | 'getSpecProperty' {
+  'setSpecProperty' | 'setSuiteProperty' | 'throwUnless' | 'throwUnlessAsync' | 'getSpecProperty' {
   return UNSUPPORTED_GLOBAL_FUNCTION_CATEGORIES.has(methodName as TodoCategory);
 }
 
diff --git a/packages/schematics/angular/refactor/jasmine-vitest/transformers/jasmine-misc_spec.ts b/packages/schematics/angular/refactor/jasmine-vitest/transformers/jasmine-misc_spec.ts
index a5b29f2d2b6a..49cb2d54475a 100644
--- a/packages/schematics/angular/refactor/jasmine-vitest/transformers/jasmine-misc_spec.ts
+++ b/packages/schematics/angular/refactor/jasmine-vitest/transformers/jasmine-misc_spec.ts
@@ -59,19 +59,31 @@ jasmine.clock().withMock(noop);`,
 describe('transformFail', () => {
   const testCases = [
     {
-      description: 'should transform fail() to throw new Error()',
+      description: 'should transform fail() to expect.fail()',
       input: `fail('This should not happen');`,
-      expected: `throw new Error('This should not happen');`,
+      expected: `expect.fail('This should not happen');`,
     },
     {
-      description: 'should transform fail() without a message to throw new Error()',
+      description: 'should transform fail() without a message to expect.fail()',
       input: `fail();`,
-      expected: `throw new Error();`,
+      expected: `expect.fail();`,
     },
     {
       description: 'should transform fail() with an Error object',
       input: `fail(new TypeError('Invalid input'));`,
-      expected: `throw new TypeError('Invalid input');`,
+      expected: `expect.fail('Invalid input');`,
+    },
+    {
+      description: 'should transform fail() with an empty Error object',
+      input: `fail(new Error());`,
+      expected: `expect.fail();`,
+    },
+    {
+      description: 'should transform fail() with a non-string argument and add a TODO note',
+      input: `fail(err);`,
+      // eslint-disable-next-line max-len
+      expected: `// TODO: vitest-migration: expect.fail() only accepts a string message. Verify that converting this argument with String() produces the expected failure output. See: https://vitest.dev/api/expect.html#expect-fail
+expect.fail(String(err));`,
     },
   ];
 
diff --git a/packages/schematics/angular/refactor/jasmine-vitest/utils/todo-notes.ts b/packages/schematics/angular/refactor/jasmine-vitest/utils/todo-notes.ts
index 598606d7bde6..0179a0314277 100644
--- a/packages/schematics/angular/refactor/jasmine-vitest/utils/todo-notes.ts
+++ b/packages/schematics/angular/refactor/jasmine-vitest/utils/todo-notes.ts
@@ -64,6 +64,12 @@ export const TODO_NOTES = {
     message:
       'expect().nothing() has been removed because it is redundant in Vitest. Tests without assertions pass by default.',
   },
+  'fail-non-string-argument': {
+    message:
+      'expect.fail() only accepts a string message. ' +
+      'Verify that converting this argument with String() produces the expected failure output.',
+    url: 'https://vitest.dev/api/expect.html#expect-fail',
+  },
   'unsupported-jasmine-member': {
     message: (context: { name: string }): string => `jasmine.${context.name} is not supported.`,
   },