diff --git a/src/cli/cli.spec.ts b/src/cli/cli.spec.ts
index fa5891a3709..08062ce1711 100644
--- a/src/cli/cli.spec.ts
+++ b/src/cli/cli.spec.ts
@@ -280,6 +280,25 @@ class MockCommandWithSchemaAndRequiredOptions extends AnonymousCommand {
   }
 }
 
+class MockCommandWithSchemaAndBoolRequiredOption extends AnonymousCommand {
+  public get name(): string {
+    return 'cli mock schema bool required';
+  }
+  public get description(): string {
+    return 'Mock command with schema and required options';
+  }
+  public get schema(): z.ZodTypeAny {
+    return globalOptionsZod
+      .extend({
+        url: z.string(),
+        bool: z.boolean()
+      })
+      .strict();
+  }
+  public async commandAction(): Promise<void> {
+  }
+}
+
 describe('cli', () => {
   let rootFolder: string;
   let cliLogStub: sinon.SinonStub;
@@ -295,6 +314,7 @@ describe('cli', () => {
   let mockCommandWithValidation: Command;
   let mockCommandWithSchema: Command;
   let mockCommandWithSchemaAndRequiredOptions: Command;
+  let mockCommandWithSchemaAndBoolRequiredOption: Command;
   let log: string[] = [];
   let mockCommandWithBooleanRewrite: Command;
 
@@ -318,6 +338,7 @@ describe('cli', () => {
     mockCommandWithValidation = new MockCommandWithValidation();
     mockCommandWithSchema = new MockCommandWithSchema();
     mockCommandWithSchemaAndRequiredOptions = new MockCommandWithSchemaAndRequiredOptions();
+    mockCommandWithSchemaAndBoolRequiredOption = new MockCommandWithSchemaAndBoolRequiredOption();
     mockCommandWithOptionSets = new MockCommandWithOptionSets();
     mockCommandActionSpy = sinon.spy(mockCommand, 'action');
 
@@ -339,6 +360,7 @@ describe('cli', () => {
       cli.getCommandInfo(mockCommandWithValidation, 'cli-validation-mock.js', 'help.mdx'),
       cli.getCommandInfo(mockCommandWithSchema, 'cli-schema-mock.js', 'help.mdx'),
       cli.getCommandInfo(mockCommandWithSchemaAndRequiredOptions, 'cli-schema-mock.js', 'help.mdx'),
+      cli.getCommandInfo(mockCommandWithSchemaAndBoolRequiredOption, 'cli-schema-mock.js', 'help.mdx'),
       cli.getCommandInfo(cliCompletionUpdateCommand, 'cli/commands/completion/completion-clink-update.js', 'cli/completion/completion-clink-update.mdx'),
       cli.getCommandInfo(mockCommandWithBooleanRewrite, 'cli-boolean-rewrite-mock.js', 'help.mdx')
     ];
@@ -1093,6 +1115,29 @@ describe('cli', () => {
       });
   });
 
+  it(`throws error if coercing value fails when validating schema`, (done) => {
+    cli.commandToExecute = cli.commands.find(c => c.name === 'cli mock schema bool required');
+    sinon.stub(cli, 'getSettingWithDefaultValue').callsFake((settingName, defaultValue) => {
+      if (settingName === settingsNames.prompt) {
+        return true;
+      }
+      return defaultValue;
+    });
+    sinon.stub(cli, 'promptForValue').resolves('nonbool');
+    const executeCommandSpy = sinon.spy(cli, 'executeCommand');
+    cli
+      .execute(['cli', 'mock', 'schema', 'bool', 'required', '--url', 'https://contoso.sharepoint.com'])
+      .then(_ => done('Promise fulfilled while error expected'), _ => {
+        try {
+          assert(executeCommandSpy.notCalled);
+          done();
+        }
+        catch (e) {
+          done(e);
+        }
+      });
+  });
+
   it(`throws an error when command's schema-based validation failed`, (done) => {
     cli.commandToExecute = cli.commands.find(c => c.name === 'cli mock schema');
     const mockCommandWithSchemaActionSpy: sinon.SinonSpy = sinon.spy(mockCommandWithSchema, 'action');
@@ -1689,7 +1734,7 @@ describe('cli', () => {
     await cli.loadCommandFromArgs(['spo', 'site', 'list']);
     cli.printAvailableCommands();
 
-    assert(cliLogStub.calledWith('  cli *  10 commands'));
+    assert(cliLogStub.calledWith('  cli *  11 commands'));
   });
 
   it(`prints commands from the specified group`, async () => {
@@ -1702,7 +1747,7 @@ describe('cli', () => {
     };
     cli.printAvailableCommands();
 
-    assert(cliLogStub.calledWith('  cli mock *        7 commands'));
+    assert(cliLogStub.calledWith('  cli mock *        8 commands'));
   });
 
   it(`prints commands from the root group when the specified string doesn't match any group`, async () => {
@@ -1715,7 +1760,7 @@ describe('cli', () => {
     };
     cli.printAvailableCommands();
 
-    assert(cliLogStub.calledWith('  cli *  10 commands'));
+    assert(cliLogStub.calledWith('  cli *  11 commands'));
   });
 
   it(`runs properly when context file not found`, async () => {
diff --git a/src/cli/cli.ts b/src/cli/cli.ts
index be5a5e60394..774d63ba719 100644
--- a/src/cli/cli.ts
+++ b/src/cli/cli.ts
@@ -194,9 +194,17 @@ async function execute(rawArgs: string[]): Promise<void> {
           await cli.error('🌶️  Provide values for the following parameters:');
 
           for (const error of result.error.errors) {
-            const optionInfo = cli.commandToExecute!.options.find(o => o.name === error.path.join('.'));
+            const optionName = error.path.join('.');
+            const optionInfo = cli.commandToExecute.options.find(o => o.name === optionName);
             const answer = await cli.promptForValue(optionInfo!);
-            cli.optionsFromArgs!.options[error.path.join('.')] = answer;
+            // coerce the answer to the correct type
+            try {
+              const parsed = getCommandOptionsFromArgs([`--${optionName}`, answer], cli.commandToExecute);
+              cli.optionsFromArgs.options[optionName] = parsed[optionName];
+            }
+            catch (e: any) {
+              return cli.closeWithError(e.message, cli.optionsFromArgs, true);
+            }
           }
         }
         else {