diff --git a/packages/aws-cdk/lib/commands/flag-operations.ts b/packages/aws-cdk/lib/commands/flag-operations.ts
index 334be5740..d2128afd9 100644
--- a/packages/aws-cdk/lib/commands/flag-operations.ts
+++ b/packages/aws-cdk/lib/commands/flag-operations.ts
@@ -128,7 +128,7 @@ export async function handleFlags(flagData: FeatureFlag[], ioHelper: IoHelper, o
   }
 
   if (options.unconfigured && options.FLAGNAME) {
-    await ioHelper.defaults.error('Error: Cannot use --unconfigured with a specific flag name. --unconfigured works on multiple flags.');
+    await ioHelper.defaults.error('Error: Cannot use --unconfigured with a specific flag name. --unconfigured works with multiple flags.');
     return;
   }
 
@@ -147,6 +147,11 @@ export async function handleFlags(flagData: FeatureFlag[], ioHelper: IoHelper, o
     return;
   }
 
+  if (options.set && !options.all && !options.unconfigured && !options.FLAGNAME) {
+    await ioHelper.defaults.error('Error: When using --set, you must specify either --all, --unconfigured, or provide a specific flag name.');
+    return;
+  }
+
   if (options.FLAGNAME && !options.set && !options.value) {
     await displayFlags(params);
     return;
diff --git a/packages/aws-cdk/test/commands/flag-operations.test.ts b/packages/aws-cdk/test/commands/flag-operations.test.ts
index 01c4f1fc6..a8e4c8b83 100644
--- a/packages/aws-cdk/test/commands/flag-operations.test.ts
+++ b/packages/aws-cdk/test/commands/flag-operations.test.ts
@@ -189,6 +189,68 @@ describe('displayFlags', () => {
     expect(plainTextOutput).toContain('different-module');
   });
 
+  test('sorts flags by module name and then by flag name within module', async () => {
+    // This test targets the sorting logic in displayFlagTable:
+    // if (a.module !== b.module) { return a.module.localeCompare(b.module); }
+    // return a.name.localeCompare(b.name);
+
+    const flagsForSortingTest: FeatureFlag[] = [
+      {
+        module: 'z-module',
+        name: '@aws-cdk/z:flagB',
+        recommendedValue: 'true',
+        userValue: undefined,
+        explanation: 'Flag B in Z module',
+      },
+      {
+        module: 'a-module',
+        name: '@aws-cdk/a:flagZ',
+        recommendedValue: 'true',
+        userValue: undefined,
+        explanation: 'Flag Z in A module',
+      },
+      {
+        module: 'a-module',
+        name: '@aws-cdk/a:flagA',
+        recommendedValue: 'true',
+        userValue: undefined,
+        explanation: 'Flag A in A module',
+      },
+      {
+        module: 'z-module',
+        name: '@aws-cdk/z:flagA',
+        recommendedValue: 'true',
+        userValue: undefined,
+        explanation: 'Flag A in Z module',
+      },
+    ];
+
+    const params = {
+      flagData: flagsForSortingTest,
+      toolkit: mockToolkit,
+      ioHelper,
+      all: true,
+    };
+    await displayFlags(params);
+
+    const plainTextOutput = output();
+
+    // Verify that modules are sorted alphabetically (a-module before z-module)
+    const aModuleIndex = plainTextOutput.indexOf('Module: a-module');
+    const zModuleIndex = plainTextOutput.indexOf('Module: z-module');
+    expect(aModuleIndex).toBeLessThan(zModuleIndex);
+
+    // Verify that within a-module, flags are sorted alphabetically (flagA before flagZ)
+    const flagAIndex = plainTextOutput.indexOf('@aws-cdk/a:flagA');
+    const flagZIndex = plainTextOutput.indexOf('@aws-cdk/a:flagZ');
+    expect(flagAIndex).toBeLessThan(flagZIndex);
+
+    // Verify that within z-module, flags are sorted alphabetically (flagA before flagB)
+    const zFlagAIndex = plainTextOutput.indexOf('@aws-cdk/z:flagA');
+    const zFlagBIndex = plainTextOutput.indexOf('@aws-cdk/z:flagB');
+    expect(zFlagAIndex).toBeLessThan(zFlagBIndex);
+  });
+
   test('does not display flag when unconfigured behavior is the same as recommended behavior', async () => {
     const params = {
       flagData: mockFlagsData,
@@ -491,6 +553,295 @@ describe('handleFlags', () => {
     const plainTextOutput = output();
     expect(plainTextOutput).toContain('The \'cdk flags\' command is not compatible with the AWS CDK library used by your application. Please upgrade to 2.212.0 or above.');
   });
+
+  test('shows error when --set is used without required options', async () => {
+    const options: FlagsOptions = {
+      set: true,
+    };
+
+    await handleFlags(mockFlagsData, ioHelper, options, mockToolkit);
+
+    const plainTextOutput = output();
+    expect(plainTextOutput).toContain('Error: When using --set, you must specify either --all, --unconfigured, or provide a specific flag name.');
+  });
+
+  test('shows error when --set is used with --recommended but no target flags', async () => {
+    const options: FlagsOptions = {
+      set: true,
+      recommended: true,
+    };
+
+    await handleFlags(mockFlagsData, ioHelper, options, mockToolkit);
+
+    const plainTextOutput = output();
+    expect(plainTextOutput).toContain('Error: When using --set, you must specify either --all, --unconfigured, or provide a specific flag name.');
+  });
+
+  test('shows error when using both --all and a specific flag name', async () => {
+    const options: FlagsOptions = {
+      FLAGNAME: ['@aws-cdk/core:testFlag'],
+      all: true,
+    };
+
+    await handleFlags(mockFlagsData, ioHelper, options, mockToolkit);
+
+    const plainTextOutput = output();
+    expect(plainTextOutput).toContain('Error: Cannot use both --all and a specific flag name. Please use either --all to show all flags or specify a single flag name.');
+  });
+
+  test('shows error when using options without --set', async () => {
+    const options: FlagsOptions = {
+      value: 'true',
+    };
+
+    await handleFlags(mockFlagsData, ioHelper, options, mockToolkit);
+
+    const plainTextOutput = output();
+    expect(plainTextOutput).toContain('Error: This option can only be used with --set.');
+  });
+
+  test('shows error when using --value without a specific flag name', async () => {
+    const options: FlagsOptions = {
+      value: 'true',
+      set: true,
+    };
+
+    await handleFlags(mockFlagsData, ioHelper, options, mockToolkit);
+
+    const plainTextOutput = output();
+    expect(plainTextOutput).toContain('Error: --value requires a specific flag name. Please specify a flag name when providing a value.');
+  });
+
+  test('shows error when using both --recommended and --default', async () => {
+    const options: FlagsOptions = {
+      recommended: true,
+      default: true,
+      set: true,
+      all: true,
+    };
+
+    await handleFlags(mockFlagsData, ioHelper, options, mockToolkit);
+
+    const plainTextOutput = output();
+    expect(plainTextOutput).toContain('Error: Cannot use both --recommended and --default. Please choose one option.');
+  });
+
+  test('shows error when using both --unconfigured and --all', async () => {
+    const options: FlagsOptions = {
+      set: true,
+      unconfigured: true,
+      all: true,
+    };
+
+    await handleFlags(mockFlagsData, ioHelper, options, mockToolkit);
+
+    const plainTextOutput = output();
+    expect(plainTextOutput).toContain('Error: Cannot use both --unconfigured and --all. Please choose one option.');
+  });
+
+  test('shows error when using both --unconfigured and a specific flag name', async () => {
+    const options: FlagsOptions = {
+      set: true,
+      unconfigured: true,
+      FLAGNAME: ['@aws-cdk/core:testFlag'],
+    };
+
+    await handleFlags(mockFlagsData, ioHelper, options, mockToolkit);
+
+    const plainTextOutput = output();
+    expect(plainTextOutput).toContain('Error: Cannot use --unconfigured with a specific flag name. --unconfigured works with multiple flags.');
+  });
+
+  test('shows error when setting a flag without providing a value', async () => {
+    const options: FlagsOptions = {
+      set: true,
+      FLAGNAME: ['@aws-cdk/core:testFlag'],
+    };
+
+    await handleFlags(mockFlagsData, ioHelper, options, mockToolkit);
+
+    const plainTextOutput = output();
+    expect(plainTextOutput).toContain('Error: When setting a specific flag, you must provide a --value.');
+  });
+
+  test('shows error when using --set with --all without --recommended or --default', async () => {
+    const options: FlagsOptions = {
+      set: true,
+      all: true,
+    };
+
+    await handleFlags(mockFlagsData, ioHelper, options, mockToolkit);
+
+    const plainTextOutput = output();
+    expect(plainTextOutput).toContain('Error: When using --set with --all, you must specify either --recommended or --default.');
+  });
+
+  test('shows error when using --set with --unconfigured without --recommended or --default', async () => {
+    const options: FlagsOptions = {
+      set: true,
+      unconfigured: true,
+    };
+
+    await handleFlags(mockFlagsData, ioHelper, options, mockToolkit);
+
+    const plainTextOutput = output();
+    expect(plainTextOutput).toContain('Error: When using --set with --unconfigured, you must specify either --recommended or --default.');
+  });
+
+  test('shows error when trying to set a flag that does not exist', async () => {
+    const options: FlagsOptions = {
+      set: true,
+      FLAGNAME: ['@aws-cdk/core:nonExistentFlag'],
+      value: 'true',
+    };
+
+    await handleFlags(mockFlagsData, ioHelper, options, mockToolkit);
+
+    const plainTextOutput = output();
+    expect(plainTextOutput).toContain('Flag not found.');
+  });
+
+  test('calls setMultipleFlagsIfSupported when using --set with --unconfigured and --default', async () => {
+    const flagsWithUnconfiguredBehavior: FeatureFlag[] = [
+      {
+        module: 'aws-cdk-lib',
+        name: '@aws-cdk/core:flagWithV2True',
+        recommendedValue: 'false',
+        userValue: undefined,
+        explanation: 'Flag with unconfiguredBehavesLike.v2 = true',
+        unconfiguredBehavesLike: { v2: 'true' },
+      },
+      {
+        module: 'aws-cdk-lib',
+        name: '@aws-cdk/core:flagWithV2False',
+        recommendedValue: 'false',
+        userValue: undefined,
+        explanation: 'Flag with unconfiguredBehavesLike.v2 = false',
+        unconfiguredBehavesLike: { v2: 'false' },
+      },
+    ];
+
+    const cdkJsonPath = await createCdkJsonFile({});
+
+    setupMockToolkitForPrototyping(mockToolkit);
+
+    const requestResponseSpy = jest.spyOn(ioHelper, 'requestResponse');
+    requestResponseSpy.mockResolvedValue(true);
+
+    const options: FlagsOptions = {
+      set: true,
+      unconfigured: true,
+      default: true,
+    };
+
+    await handleFlags(flagsWithUnconfiguredBehavior, ioHelper, options, mockToolkit);
+
+    // Verify that the prototyping process was called (indicating setMultipleFlagsIfSupported was executed)
+    expect(mockToolkit.fromCdkApp).toHaveBeenCalled();
+    expect(mockToolkit.synth).toHaveBeenCalled();
+    expect(mockToolkit.diff).toHaveBeenCalled();
+    expect(requestResponseSpy).toHaveBeenCalled();
+
+    // Verify that the flags were set to their default values based on unconfiguredBehavesLike.v2
+    const updatedContent = await fs.promises.readFile(cdkJsonPath, 'utf-8');
+    const updatedJson = JSON.parse(updatedContent);
+
+    expect(updatedJson.context['@aws-cdk/core:flagWithV2True']).toBe(true);
+    expect(updatedJson.context['@aws-cdk/core:flagWithV2False']).toBe(false);
+
+    await cleanupCdkJsonFile(cdkJsonPath);
+    requestResponseSpy.mockRestore();
+  });
+
+  test('handles boolean flag values correctly in toBooleanValue function', async () => {
+    const flagsWithBooleanRecommendedValues: FeatureFlag[] = [
+      {
+        module: 'aws-cdk-lib',
+        name: '@aws-cdk/core:booleanTrueFlag',
+        recommendedValue: true,
+        userValue: undefined,
+        explanation: 'Flag with boolean true recommended value',
+      },
+      {
+        module: 'aws-cdk-lib',
+        name: '@aws-cdk/core:booleanFalseFlag',
+        recommendedValue: false,
+        userValue: undefined,
+        explanation: 'Flag with boolean false recommended value',
+      },
+    ];
+
+    const cdkJsonPath = await createCdkJsonFile({});
+
+    setupMockToolkitForPrototyping(mockToolkit);
+
+    const requestResponseSpy = jest.spyOn(ioHelper, 'requestResponse');
+    requestResponseSpy.mockResolvedValue(true);
+
+    const options: FlagsOptions = {
+      set: true,
+      all: true,
+      recommended: true,
+    };
+
+    await handleFlags(flagsWithBooleanRecommendedValues, ioHelper, options, mockToolkit);
+
+    // Verify that the flags were set correctly using boolean values
+    const updatedContent = await fs.promises.readFile(cdkJsonPath, 'utf-8');
+    const updatedJson = JSON.parse(updatedContent);
+
+    // These should be set to their boolean recommended values, testing the toBooleanValue boolean branch
+    expect(updatedJson.context['@aws-cdk/core:booleanTrueFlag']).toBe(true);
+    expect(updatedJson.context['@aws-cdk/core:booleanFalseFlag']).toBe(false);
+
+    await cleanupCdkJsonFile(cdkJsonPath);
+    requestResponseSpy.mockRestore();
+  });
+
+  test('shows error when flag is not found during prototypeChanges', async () => {
+    // This test targets the validation in prototypeChanges function:
+    // if (!flag) { await ioHelper.defaults.error(`Flag ${flagName} not found.`); return false; }
+
+    const cdkJsonPath = await createCdkJsonFile({});
+
+    setupMockToolkitForPrototyping(mockToolkit);
+
+    // Create a scenario where we try to set multiple flags but one doesn't exist
+    // We'll mock the internal flag lookup to simulate a missing flag during the prototyping process
+    const originalFind = Array.prototype.find;
+    let findCallCount = 0;
+
+    // Mock Array.find to return undefined for the second call (simulating missing flag in prototypeChanges)
+    Array.prototype.find = function(this: any[], callback: any) {
+      findCallCount++;
+      // First call is in handleFlags validation (should find the flag)
+      // Second call is in prototypeChanges (should not find the flag to trigger our test case)
+      if (findCallCount === 2) {
+        return undefined; // Simulate flag not found in prototypeChanges
+      }
+      return originalFind.call(this, callback);
+    };
+
+    const options: FlagsOptions = {
+      set: true,
+      all: true,
+      recommended: true,
+    };
+
+    await handleFlags(mockFlagsData, ioHelper, options, mockToolkit);
+
+    const plainTextOutput = output();
+    expect(plainTextOutput).toContain('Flag @aws-cdk/s3:anotherFlag not found.');
+
+    // Verify that prototyping was attempted but failed due to missing flag
+    expect(mockToolkit.fromCdkApp).toHaveBeenCalledTimes(1); // Only the initial call, not the modified one
+    expect(mockToolkit.diff).not.toHaveBeenCalled(); // Diff should not be called due to early return
+
+    // Restore original Array.find
+    Array.prototype.find = originalFind;
+
+    await cleanupCdkJsonFile(cdkJsonPath);
+  });
 });
 
 describe('modifyValues', () => {