diff --git a/packages/cli/src/config/settingsSchema.ts b/packages/cli/src/config/settingsSchema.ts
index 4701abc1a..f9c043b3d 100644
--- a/packages/cli/src/config/settingsSchema.ts
+++ b/packages/cli/src/config/settingsSchema.ts
@@ -76,6 +76,29 @@ export interface SettingDefinition {
   mergeStrategy?: MergeStrategy;
   /** Enum type options  */
   options?: readonly SettingEnumOption[];
+  /** Schema for array items when type is 'array' */
+  items?: SettingItemDefinition;
+}
+
+/**
+ * Schema definition for array item types.
+ * Supports simple types (string, number, boolean) and complex object types.
+ */
+export interface SettingItemDefinition {
+  type: 'string' | 'number' | 'boolean' | 'object';
+  properties?: Record<
+    string,
+    SettingItemDefinition & {
+      required?: boolean;
+      enum?: string[];
+      additionalProperties?: SettingItemDefinition;
+    }
+  >;
+  items?: SettingItemDefinition;
+  required?: boolean;
+  enum?: string[];
+  description?: string;
+  additionalProperties?: boolean | SettingItemDefinition;
 }
 
 export interface SettingsSchema {
@@ -1233,6 +1256,67 @@ const SETTINGS_SCHEMA = {
           'Hooks that execute before agent processing. Can modify prompts or inject context.',
         showInDialog: false,
         mergeStrategy: MergeStrategy.CONCAT,
+        items: {
+          type: 'object',
+          description:
+            'A hook definition with an optional matcher and a list of hook configurations.',
+          properties: {
+            matcher: {
+              type: 'string',
+              description:
+                'An optional matcher pattern to filter when this hook definition applies.',
+            },
+            sequential: {
+              type: 'boolean',
+              description:
+                'Whether the hooks should be executed sequentially instead of in parallel.',
+            },
+            hooks: {
+              type: 'object',
+              description: 'The list of hook configurations to execute.',
+              required: true,
+              items: {
+                type: 'object',
+                description:
+                  'A hook configuration entry that defines a command to execute.',
+                properties: {
+                  type: {
+                    type: 'string',
+                    description: 'The type of hook.',
+                    enum: ['command'],
+                    required: true,
+                  },
+                  command: {
+                    type: 'string',
+                    description:
+                      'The command to execute when the hook is triggered.',
+                    required: true,
+                  },
+                  name: {
+                    type: 'string',
+                    description: 'An optional name for the hook.',
+                  },
+                  description: {
+                    type: 'string',
+                    description:
+                      'An optional description of what the hook does.',
+                  },
+                  timeout: {
+                    type: 'number',
+                    description:
+                      'Timeout in milliseconds for the hook execution.',
+                  },
+                  env: {
+                    type: 'object',
+                    description:
+                      'Environment variables to set when executing the hook command.',
+                    additionalProperties: { type: 'string' },
+                  },
+                },
+              },
+            },
+          },
+        },
       },
       Stop: {
         type: 'array',
@@ -1244,6 +1328,67 @@ const SETTINGS_SCHEMA = {
           'Hooks that execute after agent processing. Can post-process responses or log interactions.',
         showInDialog: false,
         mergeStrategy: MergeStrategy.CONCAT,
+        items: {
+          type: 'object',
+          description:
+            'A hook definition with an optional matcher and a list of hook configurations.',
+          properties: {
+            matcher: {
+              type: 'string',
+              description:
+                'An optional matcher pattern to filter when this hook definition applies.',
+            },
+            sequential: {
+              type: 'boolean',
+              description:
+                'Whether the hooks should be executed sequentially instead of in parallel.',
+            },
+            hooks: {
+              type: 'object',
+              description: 'The list of hook configurations to execute.',
+              required: true,
+              items: {
+                type: 'object',
+                description:
+                  'A hook configuration entry that defines a command to execute.',
+                properties: {
+                  type: {
+                    type: 'string',
+                    description: 'The type of hook.',
+                    enum: ['command'],
+                    required: true,
+                  },
+                  command: {
+                    type: 'string',
+                    description:
+                      'The command to execute when the hook is triggered.',
+                    required: true,
+                  },
+                  name: {
+                    type: 'string',
+                    description: 'An optional name for the hook.',
+                  },
+                  description: {
+                    type: 'string',
+                    description:
+                      'An optional description of what the hook does.',
+                  },
+                  timeout: {
+                    type: 'number',
+                    description:
+                      'Timeout in milliseconds for the hook execution.',
+                  },
+                  env: {
+                    type: 'object',
+                    description:
+                      'Environment variables to set when executing the hook command.',
+                    additionalProperties: { type: 'string' },
+                  },
+                },
+              },
+            },
+          },
+        },
       },
     },
   },
diff --git a/packages/vscode-ide-companion/schemas/settings.schema.json b/packages/vscode-ide-companion/schemas/settings.schema.json
index d0eef6ae9..f063da94d 100644
--- a/packages/vscode-ide-companion/schemas/settings.schema.json
+++ b/packages/vscode-ide-companion/schemas/settings.schema.json
@@ -600,14 +600,124 @@
           "description": "Hooks that execute before agent processing. Can modify prompts or inject context.",
           "type": "array",
           "items": {
-            "type": "string"
+            "description": "A hook definition with an optional matcher and a list of hook configurations.",
+            "type": "object",
+            "properties": {
+              "matcher": {
+                "description": "An optional matcher pattern to filter when this hook definition applies.",
+                "type": "string"
+              },
+              "sequential": {
+                "description": "Whether the hooks should be executed sequentially instead of in parallel.",
+                "type": "boolean"
+              },
+              "hooks": {
+                "description": "The list of hook configurations to execute.",
+                "type": "array",
+                "items": {
+                  "description": "A hook configuration entry that defines a command to execute.",
+                  "type": "object",
+                  "properties": {
+                    "type": {
+                      "description": "The type of hook.",
+                      "type": "string",
+                      "enum": [
+                        "command"
+                      ]
+                    },
+                    "command": {
+                      "description": "The command to execute when the hook is triggered.",
+                      "type": "string"
+                    },
+                    "name": {
+                      "description": "An optional name for the hook.",
+                      "type": "string"
+                    },
+                    "description": {
+                      "description": "An optional description of what the hook does.",
+                      "type": "string"
+                    },
+                    "timeout": {
+                      "description": "Timeout in milliseconds for the hook execution.",
+                      "type": "number"
+                    },
+                    "env": {
+                      "description": "Environment variables to set when executing the hook command.",
+                      "type": "object"
+                    }
+                  },
+                  "required": [
+                    "type",
+                    "command"
+                  ]
+                }
+              }
+            },
+            "required": [
+              "hooks"
+            ]
           }
         },
         "Stop": {
           "description": "Hooks that execute after agent processing. Can post-process responses or log interactions.",
           "type": "array",
           "items": {
-            "type": "string"
+            "description": "A hook definition with an optional matcher and a list of hook configurations.",
+            "type": "object",
+            "properties": {
+              "matcher": {
+                "description": "An optional matcher pattern to filter when this hook definition applies.",
+                "type": "string"
+              },
+              "sequential": {
+                "description": "Whether the hooks should be executed sequentially instead of in parallel.",
+                "type": "boolean"
+              },
+              "hooks": {
+                "description": "The list of hook configurations to execute.",
+                "type": "array",
+                "items": {
+                  "description": "A hook configuration entry that defines a command to execute.",
+                  "type": "object",
+                  "properties": {
+                    "type": {
+                      "description": "The type of hook.",
+                      "type": "string",
+                      "enum": [
+                        "command"
+                      ]
+                    },
+                    "command": {
+                      "description": "The command to execute when the hook is triggered.",
+                      "type": "string"
+                    },
+                    "name": {
+                      "description": "An optional name for the hook.",
+                      "type": "string"
+                    },
+                    "description": {
+                      "description": "An optional description of what the hook does.",
+                      "type": "string"
+                    },
+                    "timeout": {
+                      "description": "Timeout in milliseconds for the hook execution.",
+                      "type": "number"
+                    },
+                    "env": {
+                      "description": "Environment variables to set when executing the hook command.",
+                      "type": "object"
+                    }
+                  },
+                  "required": [
+                    "type",
+                    "command"
+                  ]
+                }
+              }
+            },
+            "required": [
+              "hooks"
+            ]
           }
         }
       }
diff --git a/scripts/generate-settings-schema.ts b/scripts/generate-settings-schema.ts
index 9d13e8166..272d722d1 100644
--- a/scripts/generate-settings-schema.ts
+++ b/scripts/generate-settings-schema.ts
@@ -21,6 +21,7 @@ import { fileURLToPath } from 'node:url';
 
 import type {
   SettingDefinition,
+  SettingItemDefinition,
   SettingsSchema,
 } from '../packages/cli/src/config/settingsSchema.js';
 import { getSettingsSchema } from '../packages/cli/src/config/settingsSchema.js';
@@ -37,6 +38,57 @@ interface JsonSchemaProperty {
   enum?: (string | number)[];
   default?: unknown;
   additionalProperties?: boolean | JsonSchemaProperty;
+  required?: string[];
+}
+
+function convertItemDefinitionToJsonSchema(
+  itemDef: SettingItemDefinition,
+): JsonSchemaProperty {
+  const schema: JsonSchemaProperty = {};
+
+  if (itemDef.description) {
+    schema.description = itemDef.description;
+  }
+
+  schema.type = itemDef.type;
+
+  if (itemDef.enum) {
+    schema.enum = itemDef.enum;
+  }
+
+  if (itemDef.type === 'object' && itemDef.properties) {
+    schema.properties = {};
+    const requiredFields: string[] = [];
+
+    for (const [key, childDef] of Object.entries(itemDef.properties)) {
+      const childSchema = convertItemDefinitionToJsonSchema(childDef);
+      schema.properties[key] = childSchema;
+      if (childDef.required) {
+        requiredFields.push(key);
+      }
+    }
+
+    if (requiredFields.length > 0) {
+      schema.required = requiredFields;
+    }
+
+    if (itemDef.additionalProperties !== undefined) {
+      if (typeof itemDef.additionalProperties === 'boolean') {
+        schema.additionalProperties = itemDef.additionalProperties;
+      } else {
+        schema.additionalProperties = convertItemDefinitionToJsonSchema(
+          itemDef.additionalProperties,
+        );
+      }
+    }
+  }
+
+  if (itemDef.items) {
+    schema.type = 'array';
+    schema.items = convertItemDefinitionToJsonSchema(itemDef.items);
+  }
+
+  return schema;
 }
 
 function convertSettingToJsonSchema(
@@ -60,7 +112,11 @@ function convertSettingToJsonSchema(
       break;
     case 'array':
       schema.type = 'array';
-      schema.items = { type: 'string' };
+      if (setting.items) {
+        schema.items = convertItemDefinitionToJsonSchema(setting.items);
+      } else {
+        schema.items = { type: 'string' };
+      }
       break;
     case 'enum':
       if (setting.options && setting.options.length > 0) {