diff --git a/packages/angular/build/src/builders/dev-server/schema.json b/packages/angular/build/src/builders/dev-server/schema.json
index 667bde5692da..5d4cc971a1fc 100644
--- a/packages/angular/build/src/builders/dev-server/schema.json
+++ b/packages/angular/build/src/builders/dev-server/schema.json
@@ -48,6 +48,7 @@
           }
         },
         {
+          "const": true,
           "type": "boolean",
           "description": "Indicates that all hosts are allowed. This is not recommended and a security risk."
         }
diff --git a/packages/angular/cli/src/command-builder/utilities/json-schema.ts b/packages/angular/cli/src/command-builder/utilities/json-schema.ts
index 78218465cf02..0cf3bf617a07 100644
--- a/packages/angular/cli/src/command-builder/utilities/json-schema.ts
+++ b/packages/angular/cli/src/command-builder/utilities/json-schema.ts
@@ -50,6 +50,11 @@ export interface Option extends YargsOptions {
    * Type of the values in a key/value pair field.
    */
   itemValueType?: 'string';
+
+  /**
+   * The supported types of the option.
+   */
+  types?: ReadonlyArray<'string' | 'number' | 'boolean' | 'array' | 'object'>;
 }
 
 /**
@@ -82,6 +87,41 @@ function checkStringMap(keyValuePairOptions: Set<string>, args: Arguments): bool
   return true;
 }
 
+/**
+ * A Yargs coerce function that converts empty or boolean-like values to a boolean
+ * when an option supports both `boolean` and another type (such as `array` or `string`).
+ * @param value The parsed argument value.
+ * @returns A boolean if the value represents a boolean flag, otherwise the original value.
+ */
+function coerceToBoolean(value: unknown): unknown {
+  if (typeof value === 'string') {
+    if (value === '' || value === 'true') {
+      return true;
+    }
+
+    if (value === 'false') {
+      return false;
+    }
+  } else if (Array.isArray(value)) {
+    if (value.length === 0) {
+      return true;
+    }
+
+    if (value.length === 1) {
+      const firstValue = value[0];
+      if (typeof firstValue === 'boolean') {
+        return firstValue;
+      }
+
+      if (firstValue === 'true' || firstValue === 'false') {
+        return firstValue === 'true';
+      }
+    }
+  }
+
+  return value;
+}
+
 /**
  * A Yargs coerce function that converts an array of `key=value` strings to an object.
  * @param value An array of `key=value` strings.
@@ -177,6 +217,34 @@ function isSupportedArrayItemSchema(schema: json.JsonObject): boolean {
   return false;
 }
 
+/**
+ * Checks if a JSON schema node represents a supported array schema,
+ * either directly or within `oneOf`/`anyOf` subschemas.
+ * @param schema The JSON schema node to check.
+ * @returns `true` if the schema represents a supported array, otherwise `false`.
+ */
+function isSupportedArraySchema(schema: json.JsonObject): boolean {
+  if (isJsonObject(schema.items) && isSupportedArrayItemSchema(schema.items)) {
+    return true;
+  }
+
+  if (
+    json.isJsonArray(schema.oneOf) &&
+    schema.oneOf.some((item) => isJsonObject(item) && isSupportedArraySchema(item))
+  ) {
+    return true;
+  }
+
+  if (
+    json.isJsonArray(schema.anyOf) &&
+    schema.anyOf.some((item) => isJsonObject(item) && isSupportedArraySchema(item))
+  ) {
+    return true;
+  }
+
+  return false;
+}
+
 /**
  * Gets the supported types for a JSON schema node.
  * @param current The JSON schema node to get the supported types for.
@@ -198,7 +266,7 @@ function getSupportedTypes(
       case 'string':
         return true;
       case 'array':
-        return isJsonObject(current.items) && isSupportedArrayItemSchema(current.items);
+        return isSupportedArraySchema(current);
       case 'object':
         return isStringMap(current);
       default:
@@ -372,6 +440,7 @@ export async function parseJsonSchemaToOptions(
         typeof current['x-user-analytics'] === 'string' ? current['x-user-analytics'] : undefined,
       deprecated: xDeprecated === true || typeof xDeprecated === 'string' ? xDeprecated : undefined,
       positional,
+      types,
       ...(type === 'object'
         ? {
             type: 'array',
@@ -424,6 +493,7 @@ export function addSchemaOptionsToCommand<T>(
       alias,
       userAnalytics,
       type,
+      types,
       itemValueType,
       hidden,
       name,
@@ -442,13 +512,20 @@ export function addSchemaOptionsToCommand<T>(
       keyValuePairOptions.add(dashedName);
     }
 
+    let coerce: YargsOptions['coerce'];
+    if (itemValueType) {
+      coerce = coerceToStringMap;
+    } else if (type !== 'boolean' && types?.includes('boolean')) {
+      coerce = coerceToBoolean;
+    }
+
     const sharedOptions: YargsOptions & PositionalOptions = {
       alias,
       hidden,
       description,
       deprecated,
       choices,
-      coerce: itemValueType ? coerceToStringMap : undefined,
+      coerce,
       // This should only be done when `--help` is used otherwise default will override options set in angular.json.
       ...(includeDefaultValues ? { default: defaultVal } : {}),
     };
diff --git a/packages/angular/cli/src/command-builder/utilities/json-schema_spec.ts b/packages/angular/cli/src/command-builder/utilities/json-schema_spec.ts
index 117b325f26b1..dfe4c679ca8f 100644
--- a/packages/angular/cli/src/command-builder/utilities/json-schema_spec.ts
+++ b/packages/angular/cli/src/command-builder/utilities/json-schema_spec.ts
@@ -116,6 +116,20 @@ describe('parseJsonSchemaToOptions', () => {
               ],
             },
           },
+          'allowedHosts': {
+            'default': [],
+            'oneOf': [
+              {
+                'type': 'array',
+                'items': {
+                  'type': 'string',
+                },
+              },
+              {
+                'type': 'boolean',
+              },
+            ],
+          },
         },
       };
 
@@ -231,6 +245,50 @@ describe('parseJsonSchemaToOptions', () => {
       });
     });
 
+    describe('type=array in oneOf', () => {
+      it('parses valid option value when specified once', async () => {
+        expect(await parse(['--allowed-hosts', 'a.example.com', 'b.example.com'])).toEqual(
+          jasmine.objectContaining({
+            'allowedHosts': ['a.example.com', 'b.example.com'],
+          }),
+        );
+      });
+
+      it('parses valid option value when specified multiple times', async () => {
+        expect(
+          await parse(['--allowed-hosts', 'a.example.com', '--allowed-hosts', 'b.example.com']),
+        ).toEqual(
+          jasmine.objectContaining({
+            'allowedHosts': ['a.example.com', 'b.example.com'],
+          }),
+        );
+      });
+
+      it('parses as boolean true when specified without values', async () => {
+        expect(await parse(['--allowed-hosts'])).toEqual(
+          jasmine.objectContaining({
+            'allowedHosts': true,
+          }),
+        );
+      });
+
+      it('parses as boolean true when specified with =true', async () => {
+        expect(await parse(['--allowed-hosts=true'])).toEqual(
+          jasmine.objectContaining({
+            'allowedHosts': true,
+          }),
+        );
+      });
+
+      it('parses as boolean false when specified with =false', async () => {
+        expect(await parse(['--allowed-hosts=false'])).toEqual(
+          jasmine.objectContaining({
+            'allowedHosts': false,
+          }),
+        );
+      });
+    });
+
     describe('type=string, enum', () => {
       it('parses valid option value', async () => {
         expect(await parse(['--ssr', 'never'])).toEqual(