diff --git a/src/components/experimental/duo/chat/components/duo_chat_context/constants.js b/src/components/experimental/duo/chat/components/duo_chat_context/constants.js
index d1d1b777dbf775644fad584d3691a2957d88c19c..7d825c7cc9a610425bd73a1e55b8dfef36bace3d 100644
--- a/src/components/experimental/duo/chat/components/duo_chat_context/constants.js
+++ b/src/components/experimental/duo/chat/components/duo_chat_context/constants.js
@@ -1,3 +1,3 @@
-export const CONTEXT_ITEM_TYPE_ISSUE = 'issue';
-export const CONTEXT_ITEM_TYPE_MERGE_REQUEST = 'merge_request';
-export const CONTEXT_ITEM_TYPE_PROJECT_FILE = 'project_file';
+export const CONTEXT_ITEM_CATEGORY_ISSUE = 'issue';
+export const CONTEXT_ITEM_CATEGORY_MERGE_REQUEST = 'merge_request';
+export const CONTEXT_ITEM_CATEGORY_FILE = 'file';
diff --git a/src/components/experimental/duo/chat/components/duo_chat_context/duo_chat_context_item_menu/duo_chat_context_item_menu.spec.js b/src/components/experimental/duo/chat/components/duo_chat_context/duo_chat_context_item_menu/duo_chat_context_item_menu.spec.js
index 9fb517fda5dd2169692a05c005f7f972d0bee3ab..670067ddf26c04975a2552a82476151fbf1ec6c5 100644
--- a/src/components/experimental/duo/chat/components/duo_chat_context/duo_chat_context_item_menu/duo_chat_context_item_menu.spec.js
+++ b/src/components/experimental/duo/chat/components/duo_chat_context/duo_chat_context_item_menu/duo_chat_context_item_menu.spec.js
@@ -2,9 +2,9 @@ import { shallowMount } from '@vue/test-utils';
 import { nextTick } from 'vue';
 import { getMockCategory, getMockContextItems, MOCK_CATEGORIES } from '../mock_context_data';
 import {
-  CONTEXT_ITEM_TYPE_ISSUE,
-  CONTEXT_ITEM_TYPE_MERGE_REQUEST,
-  CONTEXT_ITEM_TYPE_PROJECT_FILE,
+  CONTEXT_ITEM_CATEGORY_ISSUE,
+  CONTEXT_ITEM_CATEGORY_MERGE_REQUEST,
+  CONTEXT_ITEM_CATEGORY_FILE,
 } from '../constants';
 import GlDuoChatContextItemSelections from '../duo_chat_context_item_selections/duo_chat_context_item_selections.vue';
 import GlDuoChatContextItemMenuCategoryItems from './duo_chat_context_item_menu_category_items.vue';
@@ -122,19 +122,22 @@ describe('GlDuoChatContextItemMenu', () => {
     });
 
     describe.each([
-      CONTEXT_ITEM_TYPE_ISSUE,
-      CONTEXT_ITEM_TYPE_MERGE_REQUEST,
-      CONTEXT_ITEM_TYPE_PROJECT_FILE,
+      CONTEXT_ITEM_CATEGORY_ISSUE,
+      CONTEXT_ITEM_CATEGORY_MERGE_REQUEST,
+      CONTEXT_ITEM_CATEGORY_FILE,
     ])('when a "%s" category has been selected', (categoryValue) => {
       let category;
       let results;
       beforeEach(() => {
         category = getMockCategory(categoryValue);
         results = getMockContextItems()
-          .filter((item) => item.type === categoryValue)
+          .filter((item) => item.category === categoryValue)
           .map((item, index) => ({
             ...item,
-            isEnabled: index % 2 === 0, // disable odd indexed items
+            metadata: {
+              ...item.metadata,
+              enabled: index % 2 === 0, // disable odd indexed items
+            },
           }));
 
         createComponent({
@@ -260,7 +263,10 @@ describe('GlDuoChatContextItemMenu', () => {
             await wrapper.setProps({
               results: results.map((result, index) => ({
                 ...result,
-                isEnabled: index === firstEnabledIndex,
+                metadata: {
+                  ...result.metadata,
+                  enabled: index === firstEnabledIndex,
+                },
               })),
             });
             await nextTick();
diff --git a/src/components/experimental/duo/chat/components/duo_chat_context/duo_chat_context_item_menu/duo_chat_context_item_menu.vue b/src/components/experimental/duo/chat/components/duo_chat_context/duo_chat_context_item_menu/duo_chat_context_item_menu.vue
index 65093aea2c894033162a2c136fd8eb37e1c516b7..a3fbca3a2b05f3f137bc03ea4360d167a5eaa5c2 100644
--- a/src/components/experimental/duo/chat/components/duo_chat_context/duo_chat_context_item_menu/duo_chat_context_item_menu.vue
+++ b/src/components/experimental/duo/chat/components/duo_chat_context/duo_chat_context_item_menu/duo_chat_context_item_menu.vue
@@ -77,7 +77,7 @@ export default {
       return this.open && !this.selectedCategory;
     },
     allResultsAreDisabled() {
-      return this.results.every((result) => !result.isEnabled);
+      return this.results.every((result) => !result.metadata.enabled);
     },
   },
   watch: {
@@ -90,7 +90,7 @@ export default {
       this.debouncedSearch(query);
     },
     results(newResults) {
-      const firstEnabledIndex = newResults.findIndex((result) => result.isEnabled);
+      const firstEnabledIndex = newResults.findIndex((result) => result.metadata.enabled);
       this.activeIndex = firstEnabledIndex >= 0 ? firstEnabledIndex : 0;
     },
   },
@@ -117,7 +117,7 @@ export default {
       });
     }, SEARCH_DEBOUNCE_MS),
     selectItem(item) {
-      if (!item.isEnabled) {
+      if (!item.metadata.enabled) {
         return;
       }
 
@@ -214,7 +214,7 @@ export default {
           // If we've looped through all items and found no enabled ones, keep the current index
           return;
         }
-      } while (!this.results[newIndex].isEnabled);
+      } while (!this.results[newIndex].metadata.enabled);
 
       this.activeIndex = newIndex;
     },
diff --git a/src/components/experimental/duo/chat/components/duo_chat_context/duo_chat_context_item_menu/duo_chat_context_item_menu_search_item.spec.js b/src/components/experimental/duo/chat/components/duo_chat_context/duo_chat_context_item_menu/duo_chat_context_item_menu_search_item.spec.js
index 9ddf410b2518e086a7122b689f6569a6986ca3eb..4c5eacfbcacb833d86473477e3e6fc52b5d699e4 100644
--- a/src/components/experimental/duo/chat/components/duo_chat_context/duo_chat_context_item_menu/duo_chat_context_item_menu_search_item.spec.js
+++ b/src/components/experimental/duo/chat/components/duo_chat_context/duo_chat_context_item_menu/duo_chat_context_item_menu_search_item.spec.js
@@ -6,9 +6,9 @@ import {
   MOCK_CONTEXT_ITEM_MERGE_REQUEST,
 } from '../mock_context_data';
 import {
-  CONTEXT_ITEM_TYPE_ISSUE,
-  CONTEXT_ITEM_TYPE_MERGE_REQUEST,
-  CONTEXT_ITEM_TYPE_PROJECT_FILE,
+  CONTEXT_ITEM_CATEGORY_ISSUE,
+  CONTEXT_ITEM_CATEGORY_MERGE_REQUEST,
+  CONTEXT_ITEM_CATEGORY_FILE,
 } from '../constants';
 import GlDuoChatContextItemPopover from '../duo_chat_context_item_popover/duo_chat_context_item_popover.vue';
 import GlDuoChatContextItemMenuSearchItem from './duo_chat_context_item_menu_search_item.vue';
@@ -30,15 +30,15 @@ describe('GlDuoChatContextItemMenuContextSearchItem', () => {
 
   describe.each([
     {
-      category: getMockCategory(CONTEXT_ITEM_TYPE_PROJECT_FILE),
+      category: getMockCategory(CONTEXT_ITEM_CATEGORY_FILE),
       contextItem: MOCK_CONTEXT_ITEM_FILE,
     },
     {
-      category: getMockCategory(CONTEXT_ITEM_TYPE_ISSUE),
+      category: getMockCategory(CONTEXT_ITEM_CATEGORY_ISSUE),
       contextItem: MOCK_CONTEXT_ITEM_ISSUE,
     },
     {
-      category: getMockCategory(CONTEXT_ITEM_TYPE_MERGE_REQUEST),
+      category: getMockCategory(CONTEXT_ITEM_CATEGORY_MERGE_REQUEST),
       contextItem: MOCK_CONTEXT_ITEM_MERGE_REQUEST,
     },
   ])('for "$category"', ({ category, contextItem }) => {
@@ -58,7 +58,7 @@ describe('GlDuoChatContextItemMenuContextSearchItem', () => {
     });
 
     it('renders the default context item title', () => {
-      expect(wrapper.text()).toContain(contextItem.metadata.name);
+      expect(wrapper.text()).toContain(contextItem.metadata.title);
     });
   });
 });
diff --git a/src/components/experimental/duo/chat/components/duo_chat_context/duo_chat_context_item_menu/duo_chat_context_item_menu_search_item.vue b/src/components/experimental/duo/chat/components/duo_chat_context/duo_chat_context_item_menu/duo_chat_context_item_menu_search_item.vue
index df4175b15921126db059790e72f7f1588ebd3b55..fe45351990432c8d90bc4fdc0f6486c2e39eb0b7 100644
--- a/src/components/experimental/duo/chat/components/duo_chat_context/duo_chat_context_item_menu/duo_chat_context_item_menu_search_item.vue
+++ b/src/components/experimental/duo/chat/components/duo_chat_context/duo_chat_context_item_menu/duo_chat_context_item_menu_search_item.vue
@@ -8,9 +8,9 @@ import {
   formatMergeRequestId,
 } from '../utils';
 import {
-  CONTEXT_ITEM_TYPE_ISSUE,
-  CONTEXT_ITEM_TYPE_MERGE_REQUEST,
-  CONTEXT_ITEM_TYPE_PROJECT_FILE,
+  CONTEXT_ITEM_CATEGORY_ISSUE,
+  CONTEXT_ITEM_CATEGORY_MERGE_REQUEST,
+  CONTEXT_ITEM_CATEGORY_FILE,
 } from '../constants';
 
 export default {
@@ -30,16 +30,16 @@ export default {
   },
   computed: {
     title() {
-      return this.contextItem.metadata?.name || '';
+      return this.contextItem.metadata?.title || '';
     },
     secondaryText() {
       switch (this.category.value) {
-        case CONTEXT_ITEM_TYPE_PROJECT_FILE:
-          return this.contextItem.metadata.info.relFilePath;
-        case CONTEXT_ITEM_TYPE_ISSUE:
-          return formatIssueId(this.contextItem.metadata.info.iid);
-        case CONTEXT_ITEM_TYPE_MERGE_REQUEST:
-          return formatMergeRequestId(this.contextItem.metadata.info.iid);
+        case CONTEXT_ITEM_CATEGORY_FILE:
+          return this.contextItem.metadata.relativePath;
+        case CONTEXT_ITEM_CATEGORY_ISSUE:
+          return formatIssueId(this.contextItem.metadata.iid);
+        case CONTEXT_ITEM_CATEGORY_MERGE_REQUEST:
+          return formatMergeRequestId(this.contextItem.metadata.iid);
         default:
           return '';
       }
diff --git a/src/components/experimental/duo/chat/components/duo_chat_context/duo_chat_context_item_menu/duo_chat_context_item_menu_search_items.spec.js b/src/components/experimental/duo/chat/components/duo_chat_context/duo_chat_context_item_menu/duo_chat_context_item_menu_search_items.spec.js
index 8fca41335aef1f7a7693e0f978faf613d0348c49..4757d463d98ff0d1b7396e459872624305419635 100644
--- a/src/components/experimental/duo/chat/components/duo_chat_context/duo_chat_context_item_menu/duo_chat_context_item_menu_search_items.spec.js
+++ b/src/components/experimental/duo/chat/components/duo_chat_context/duo_chat_context_item_menu/duo_chat_context_item_menu_search_items.spec.js
@@ -2,9 +2,9 @@ import { shallowMount } from '@vue/test-utils';
 import { nextTick } from 'vue';
 import { MOCK_CATEGORIES, getMockContextItems, getMockCategory } from '../mock_context_data';
 import {
-  CONTEXT_ITEM_TYPE_ISSUE,
-  CONTEXT_ITEM_TYPE_MERGE_REQUEST,
-  CONTEXT_ITEM_TYPE_PROJECT_FILE,
+  CONTEXT_ITEM_CATEGORY_ISSUE,
+  CONTEXT_ITEM_CATEGORY_MERGE_REQUEST,
+  CONTEXT_ITEM_CATEGORY_FILE,
 } from '../constants';
 import GlDuoChatContextItemMenuSearchItems from './duo_chat_context_item_menu_search_items.vue';
 import GlDuoChatContextItemMenuSearchItemsLoading from './duo_chat_context_item_menu_search_items_loading.vue';
@@ -17,7 +17,8 @@ describe('GlDuoChatContextItemMenuSearchItems', () => {
 
   const createWrapper = (props = {}) => {
     category = props.category || MOCK_CATEGORIES.at(0);
-    results = props.results || getMockContextItems().filter((item) => item.type === category.value);
+    results =
+      props.results || getMockContextItems().filter((item) => item.category === category.value);
 
     wrapper = shallowMount(GlDuoChatContextItemMenuSearchItems, {
       propsData: {
@@ -196,7 +197,10 @@ describe('GlDuoChatContextItemMenuSearchItems', () => {
           await wrapper.setProps({
             results: results.map((result, index) => ({
               ...result,
-              isEnabled: index !== disabledIndex,
+              metadata: {
+                ...result.metadata,
+                enabled: index !== disabledIndex,
+              },
             })),
           });
 
@@ -218,7 +222,10 @@ describe('GlDuoChatContextItemMenuSearchItems', () => {
           wrapper.setProps({
             results: getMockContextItems().map((result) => ({
               ...result,
-              isEnabled: false,
+              metadata: {
+                ...result.metadata,
+                enabled: false,
+              },
             })),
           });
           await nextTick();
@@ -231,15 +238,15 @@ describe('GlDuoChatContextItemMenuSearchItems', () => {
 
   describe.each([
     {
-      testCase: getMockCategory(CONTEXT_ITEM_TYPE_PROJECT_FILE),
+      testCase: getMockCategory(CONTEXT_ITEM_CATEGORY_FILE),
       expectedPlaceholder: 'Search files...',
     },
     {
-      testCase: getMockCategory(CONTEXT_ITEM_TYPE_ISSUE),
+      testCase: getMockCategory(CONTEXT_ITEM_CATEGORY_ISSUE),
       expectedPlaceholder: 'Search issues...',
     },
     {
-      testCase: getMockCategory(CONTEXT_ITEM_TYPE_MERGE_REQUEST),
+      testCase: getMockCategory(CONTEXT_ITEM_CATEGORY_MERGE_REQUEST),
       expectedPlaceholder: 'Search merge requests...',
     },
   ])('when category is "$testCase.label"', ({ testCase, expectedPlaceholder }) => {
diff --git a/src/components/experimental/duo/chat/components/duo_chat_context/duo_chat_context_item_menu/duo_chat_context_item_menu_search_items.vue b/src/components/experimental/duo/chat/components/duo_chat_context/duo_chat_context_item_menu/duo_chat_context_item_menu_search_items.vue
index 6349ca7ee6472833f7f7ff984bca6305d095470e..ca20fdb8973af41259f9c90161f2af9b85f97ef2 100644
--- a/src/components/experimental/duo/chat/components/duo_chat_context/duo_chat_context_item_menu/duo_chat_context_item_menu_search_items.vue
+++ b/src/components/experimental/duo/chat/components/duo_chat_context/duo_chat_context_item_menu/duo_chat_context_item_menu_search_items.vue
@@ -87,12 +87,12 @@ export default {
       this.$emit('keyup', e);
     },
     setActiveIndex(index) {
-      if (this.results[index]?.isEnabled) {
+      if (this.results[index]?.metadata.enabled) {
         this.$emit('active-index-change', index);
       }
     },
     isActiveItem(contextItem, index) {
-      return index === this.activeIndex && contextItem.isEnabled;
+      return index === this.activeIndex && contextItem.metadata.enabled;
     },
   },
   i18n: {
@@ -127,9 +127,10 @@ export default {
           :key="contextItem.id"
           :class="{
             'active-command': isActiveItem(contextItem, index),
-            'gl-cursor-not-allowed [&>button]:focus-within:!gl-shadow-none': !contextItem.isEnabled,
+            'gl-cursor-not-allowed [&>button]:focus-within:!gl-shadow-none':
+              !contextItem.metadata.enabled,
           }"
-          :tabindex="!contextItem.isEnabled ? -1 : undefined"
+          :tabindex="!contextItem.metadata.enabled ? -1 : undefined"
           class="duo-chat-context-search-result-item"
           data-testid="search-result-item"
           @click="selectItem(contextItem)"
@@ -138,7 +139,7 @@ export default {
             <gl-duo-chat-context-item-menu-search-item
               :context-item="contextItem"
               :category="category"
-              :class="{ 'gl-text-secondary': !contextItem.isEnabled }"
+              :class="{ 'gl-text-secondary': !contextItem.metadata.enabled }"
               data-testid="search-result-item-details"
             />
           </div>
diff --git a/src/components/experimental/duo/chat/components/duo_chat_context/duo_chat_context_item_popover/duo_chat_context_item_popover.spec.js b/src/components/experimental/duo/chat/components/duo_chat_context/duo_chat_context_item_popover/duo_chat_context_item_popover.spec.js
index ca6f7261a948a7715489850551b07f21142fbb59..822690b68c588699b11dbe65cb01051393207b28 100644
--- a/src/components/experimental/duo/chat/components/duo_chat_context/duo_chat_context_item_popover/duo_chat_context_item_popover.spec.js
+++ b/src/components/experimental/duo/chat/components/duo_chat_context/duo_chat_context_item_popover/duo_chat_context_item_popover.spec.js
@@ -43,7 +43,7 @@ describe('GlDuoChatContextItemPopover', () => {
     expect(popover.attributes('target')).toBe('test-target');
     expect(popover.props('triggers')).toBe('hover focus');
     expect(popover.props('placement')).toBe('top');
-    expect(popover.props('title')).toBe(MOCK_CONTEXT_ITEM_FILE.metadata.name);
+    expect(popover.props('title')).toBe(MOCK_CONTEXT_ITEM_FILE.metadata.title);
   });
 
   it('renders the item name in the title slot', () => {
@@ -59,23 +59,23 @@ describe('GlDuoChatContextItemPopover', () => {
       }
     );
 
-    expect(findPopoverTitle().text()).toBe(MOCK_CONTEXT_ITEM_FILE.metadata.name);
+    expect(findPopoverTitle().text()).toBe(MOCK_CONTEXT_ITEM_FILE.metadata.title);
   });
 
   describe('item info rendering', () => {
     it.each([
-      ['file', MOCK_CONTEXT_ITEM_FILE, MOCK_CONTEXT_ITEM_FILE.metadata.info.relFilePath],
-      ['issue', MOCK_CONTEXT_ITEM_ISSUE, MOCK_CONTEXT_ITEM_ISSUE.metadata.info.iid.toString()],
+      ['file', MOCK_CONTEXT_ITEM_FILE, MOCK_CONTEXT_ITEM_FILE.metadata.relativePath],
+      ['issue', MOCK_CONTEXT_ITEM_ISSUE, MOCK_CONTEXT_ITEM_ISSUE.metadata.iid.toString()],
       [
         'merge request',
         MOCK_CONTEXT_ITEM_MERGE_REQUEST,
-        MOCK_CONTEXT_ITEM_MERGE_REQUEST.metadata.info.iid.toString(),
+        MOCK_CONTEXT_ITEM_MERGE_REQUEST.metadata.iid.toString(),
       ],
     ])('renders correct project and type for %s', (_, contextItem, expected) => {
       createComponent({ contextItem });
 
       const content = findPopover().text();
-      expect(content).toContain(contextItem.metadata.info.project);
+      expect(content).toContain(contextItem.metadata.project);
       expect(content).toContain(expected);
     });
 
@@ -83,7 +83,7 @@ describe('GlDuoChatContextItemPopover', () => {
       createComponent({ contextItem: MOCK_CONTEXT_ITEM_FILE });
 
       const content = findPopover().text();
-      expect(content).toContain(MOCK_CONTEXT_ITEM_FILE.metadata.info.relFilePath);
+      expect(content).toContain(MOCK_CONTEXT_ITEM_FILE.metadata.relativePath);
     });
 
     it.each([
@@ -109,7 +109,7 @@ describe('GlDuoChatContextItemPopover', () => {
     it('renders default disabled message when no specific reasons are provided', () => {
       const itemWithoutReasons = {
         ...MOCK_CONTEXT_ITEM_FILE_DISABLED,
-        info: { ...MOCK_CONTEXT_ITEM_FILE_DISABLED.metadata.info, disabledReasons: undefined },
+        metadata: { ...MOCK_CONTEXT_ITEM_FILE_DISABLED.metadata, disabledReasons: undefined },
       };
       createComponent({ contextItem: itemWithoutReasons });
 
diff --git a/src/components/experimental/duo/chat/components/duo_chat_context/duo_chat_context_item_popover/duo_chat_context_item_popover.stories.js b/src/components/experimental/duo/chat/components/duo_chat_context/duo_chat_context_item_popover/duo_chat_context_item_popover.stories.js
index 2cf9d2643ab52a8c5590cd2fd73add438ce64150..faaf10d6f5300ad5bb28fac3bf65edf75178399a 100644
--- a/src/components/experimental/duo/chat/components/duo_chat_context/duo_chat_context_item_popover/duo_chat_context_item_popover.stories.js
+++ b/src/components/experimental/duo/chat/components/duo_chat_context/duo_chat_context_item_popover/duo_chat_context_item_popover.stories.js
@@ -22,10 +22,10 @@ const Template = (args, { argTypes }) => ({
   template: `
     <div class="gl-flex gl-flex-col gl-items-center">
       <button :id="item.id">
-        Hover me ({{ item.type }}){{ item.isEnabled ? '' : ' (item is disabled)' }}
+        Hover me ({{ item.category }}){{ item.metadata.enabled ? '' : ' (item is disabled)' }}
       </button>
       <gl-duo-chat-context-item-popover
-        :item="item"
+        :context-item="item"
         :target="item.id"
       />
     </div>
diff --git a/src/components/experimental/duo/chat/components/duo_chat_context/duo_chat_context_item_popover/duo_chat_context_item_popover.vue b/src/components/experimental/duo/chat/components/duo_chat_context/duo_chat_context_item_popover/duo_chat_context_item_popover.vue
index b8a11e168f277f946b1395728f89b1f9a8378c6c..065a3176e50b65fdb3378ee0ab43cb441c840e6a 100644
--- a/src/components/experimental/duo/chat/components/duo_chat_context/duo_chat_context_item_popover/duo_chat_context_item_popover.vue
+++ b/src/components/experimental/duo/chat/components/duo_chat_context/duo_chat_context_item_popover/duo_chat_context_item_popover.vue
@@ -3,9 +3,9 @@ import GlPopover from '../../../../../../base/popover/popover.vue';
 import GlIcon from '../../../../../../base/icon/icon.vue';
 import { translate } from '../../../../../../../utils/i18n';
 import {
-  CONTEXT_ITEM_TYPE_ISSUE,
-  CONTEXT_ITEM_TYPE_MERGE_REQUEST,
-  CONTEXT_ITEM_TYPE_PROJECT_FILE,
+  CONTEXT_ITEM_CATEGORY_ISSUE,
+  CONTEXT_ITEM_CATEGORY_MERGE_REQUEST,
+  CONTEXT_ITEM_CATEGORY_FILE,
 } from '../constants';
 import { formatIssueId, formatMergeRequestId } from '../utils';
 import GlAlert from '../../../../../../base/alert/alert.vue';
@@ -42,44 +42,44 @@ export default {
     },
   },
   computed: {
-    itemInfo() {
-      return this.contextItem.metadata?.info || {};
-    },
     id() {
       const isIssuable =
-        this.contextItem.type === CONTEXT_ITEM_TYPE_ISSUE ||
-        this.contextItem.type === CONTEXT_ITEM_TYPE_MERGE_REQUEST;
-      return isIssuable ? this.itemInfo.iid || '' : null;
+        this.contextItem.category === CONTEXT_ITEM_CATEGORY_ISSUE ||
+        this.contextItem.category === CONTEXT_ITEM_CATEGORY_MERGE_REQUEST;
+      return isIssuable ? this.contextItem.metadata.iid : null;
     },
     formattedId() {
-      switch (this.contextItem.type) {
-        case CONTEXT_ITEM_TYPE_ISSUE:
+      switch (this.contextItem.category) {
+        case CONTEXT_ITEM_CATEGORY_ISSUE:
           return formatIssueId(this.id);
-        case CONTEXT_ITEM_TYPE_MERGE_REQUEST:
+        case CONTEXT_ITEM_CATEGORY_MERGE_REQUEST:
           return formatMergeRequestId(this.id);
         default:
           return '';
       }
     },
+    title() {
+      return this.contextItem.metadata.title || '';
+    },
     filePath() {
-      return this.contextItem.type === CONTEXT_ITEM_TYPE_PROJECT_FILE
-        ? this.itemInfo.relFilePath || ''
+      return this.contextItem.category === CONTEXT_ITEM_CATEGORY_FILE
+        ? this.contextItem.metadata.relativePath || ''
         : null;
     },
     filePathArray() {
       return this.filePath?.split('/');
     },
     isEnabled() {
-      return this.contextItem.isEnabled !== false;
+      return this.contextItem.metadata.enabled !== false;
     },
     disabledMessage() {
-      return Array.isArray(this.contextItem.disabledReasons) &&
-        this.contextItem.disabledReasons.length > 0
-        ? this.contextItem.disabledReasons.join(', ')
+      return Array.isArray(this.contextItem.metadata.disabledReasons) &&
+        this.contextItem.metadata.disabledReasons.length > 0
+        ? this.contextItem.metadata.disabledReasons.join(', ')
         : translate('DuoChatContextItemPopover.DisabledReason', 'This item is disabled');
     },
     iconName() {
-      switch (this.contextItem.type) {
+      switch (this.contextItem.category) {
         case 'merge_request':
           return 'merge-request';
         case 'issue':
@@ -89,7 +89,7 @@ export default {
       }
     },
     itemTypeLabel() {
-      switch (this.contextItem.type) {
+      switch (this.contextItem.category) {
         case 'merge_request':
           return translate('DuoChatContextItemPopover.MergeRequest', 'Merge request');
         case 'issue':
@@ -109,7 +109,7 @@ export default {
     :target="target"
     triggers="hover focus"
     :placement="placement"
-    :title="contextItem.metadata.name"
+    :title="title"
     custom-class="gl-duo-chat-item-popover"
   >
     <template #title>
@@ -118,7 +118,7 @@ export default {
           class="gl-heading-3 gl-mb-1 gl-mt-2 gl-leading-1"
           data-testid="chat-context-popover-title"
         >
-          {{ contextItem.metadata.name }}
+          {{ contextItem.metadata.title }}
         </div>
         <div class="gl-font-normal gl-text-subtle">{{ itemTypeLabel }}</div>
       </div>
@@ -126,7 +126,7 @@ export default {
     <div>
       <div v-if="filePath !== null" class="gl-flex gl-flex-wrap gl-items-center">
         <gl-icon name="document" :size="12" variant="subtle" class="gl-mr-1" />
-        <span>{{ itemInfo.project }}</span
+        <span>{{ contextItem.metadata.project }}</span
         ><span v-for="(pathPart, index) in filePathArray" :key="pathPart" class="gl-break-all"
           >{{ pathPart }}{{ index + 1 < filePathArray.length ? '/' : '' }}</span
         >
@@ -138,7 +138,7 @@ export default {
       >
         <gl-icon :name="iconName" :size="12" variant="subtle" class="gl-mr-1" />
 
-        <span>{{ itemInfo.project }}</span
+        <span>{{ contextItem.metadata.project }}</span
         ><span v-if="id !== null">{{ formattedId }}</span>
       </div>
       <gl-alert
diff --git a/src/components/experimental/duo/chat/components/duo_chat_context/duo_chat_context_item_selections/duo_chat_context_item_selections.vue b/src/components/experimental/duo/chat/components/duo_chat_context/duo_chat_context_item_selections/duo_chat_context_item_selections.vue
index e9440cf1410cc72a342ade78e726b73670a8fd26..ba1c8261165813912b5e362e8a928dedf7a65849 100644
--- a/src/components/experimental/duo/chat/components/duo_chat_context/duo_chat_context_item_selections/duo_chat_context_item_selections.vue
+++ b/src/components/experimental/duo/chat/components/duo_chat_context/duo_chat_context_item_selections/duo_chat_context_item_selections.vue
@@ -4,9 +4,9 @@ import GlIcon from '../../../../../../base/icon/icon.vue';
 import GlToken from '../../../../../../base/token/token.vue';
 import GlDuoChatContextItemPopover from '../duo_chat_context_item_popover/duo_chat_context_item_popover.vue';
 import {
-  CONTEXT_ITEM_TYPE_ISSUE,
-  CONTEXT_ITEM_TYPE_MERGE_REQUEST,
-  CONTEXT_ITEM_TYPE_PROJECT_FILE,
+  CONTEXT_ITEM_CATEGORY_ISSUE,
+  CONTEXT_ITEM_CATEGORY_MERGE_REQUEST,
+  CONTEXT_ITEM_CATEGORY_FILE,
 } from '../constants';
 import { contextItemsValidator } from '../utils';
 
@@ -78,13 +78,13 @@ export default {
     },
   },
   methods: {
-    getIconName(type) {
+    getIconName(category) {
       const iconMap = {
-        [CONTEXT_ITEM_TYPE_PROJECT_FILE]: 'document',
-        [CONTEXT_ITEM_TYPE_ISSUE]: 'issues',
-        [CONTEXT_ITEM_TYPE_MERGE_REQUEST]: 'merge-request',
+        [CONTEXT_ITEM_CATEGORY_FILE]: 'document',
+        [CONTEXT_ITEM_CATEGORY_ISSUE]: 'issues',
+        [CONTEXT_ITEM_CATEGORY_MERGE_REQUEST]: 'merge-request',
       };
-      return iconMap[type] || 'document';
+      return iconMap[category] || 'document';
     },
     toggleCollapse() {
       this.isCollapsed = !this.isCollapsed;
@@ -127,8 +127,8 @@ export default {
         @close="onRemoveItem(item)"
       >
         <div :id="`context-item-${item.id}-${selectionsId}`" class="gl-flex gl-items-center">
-          <gl-icon :name="getIconName(item.type)" :size="12" class="gl-mr-1" />
-          {{ item.metadata.name }}
+          <gl-icon :name="getIconName(item.category)" :size="12" class="gl-mr-1" />
+          {{ item.metadata.title }}
         </div>
         <gl-duo-chat-context-item-popover
           :context-item="item"
diff --git a/src/components/experimental/duo/chat/components/duo_chat_context/mock_context_data.js b/src/components/experimental/duo/chat/components/duo_chat_context/mock_context_data.js
index 2c940ad81509de30a889fdbbb9982c85d4bf719e..c17eff3e45a8656bf3195a2c3e1e0b7e8ba7349d 100644
--- a/src/components/experimental/duo/chat/components/duo_chat_context/mock_context_data.js
+++ b/src/components/experimental/duo/chat/components/duo_chat_context/mock_context_data.js
@@ -1,13 +1,13 @@
 import {
-  CONTEXT_ITEM_TYPE_ISSUE,
-  CONTEXT_ITEM_TYPE_MERGE_REQUEST,
-  CONTEXT_ITEM_TYPE_PROJECT_FILE,
+  CONTEXT_ITEM_CATEGORY_ISSUE,
+  CONTEXT_ITEM_CATEGORY_MERGE_REQUEST,
+  CONTEXT_ITEM_CATEGORY_FILE,
 } from './constants';
 
 export const MOCK_CATEGORIES = [
-  { label: 'Files', value: CONTEXT_ITEM_TYPE_PROJECT_FILE, icon: 'document' },
-  { label: 'Issues', value: CONTEXT_ITEM_TYPE_ISSUE, icon: 'issues' },
-  { label: 'Merge Requests', value: CONTEXT_ITEM_TYPE_MERGE_REQUEST, icon: 'merge-request' },
+  { label: 'Files', value: CONTEXT_ITEM_CATEGORY_FILE, icon: 'document' },
+  { label: 'Issues', value: CONTEXT_ITEM_CATEGORY_ISSUE, icon: 'issues' },
+  { label: 'Merge Requests', value: CONTEXT_ITEM_CATEGORY_MERGE_REQUEST, icon: 'merge-request' },
 ];
 
 export function getMockCategory(categoryValue) {
@@ -16,129 +16,112 @@ export function getMockCategory(categoryValue) {
 
 export const MOCK_CONTEXT_ITEM_FILE = {
   id: '123e4567-e89b-12d3-a456-426614174000',
-  isEnabled: true,
+  category: CONTEXT_ITEM_CATEGORY_FILE,
   metadata: {
-    name: 'strawberry.ts',
-    info: {
-      project: 'example/garden',
-      relFilePath: 'src/plants/strawberry.ts',
-    },
+    enabled: true,
+    title: 'strawberry.ts',
+    project: 'example/garden',
+    relativePath: 'src/plants/strawberry.ts',
   },
-  type: CONTEXT_ITEM_TYPE_PROJECT_FILE,
 };
 
 export const MOCK_CONTEXT_ITEM_FILE_DISABLED = {
   id: '323e4567-e89b-12d3-a456-426614174002',
-  isEnabled: false,
+  category: CONTEXT_ITEM_CATEGORY_FILE,
   metadata: {
-    name: 'motorbike.cs',
-    info: {
-      project: 'example/vehicles',
-      relFilePath: '/src/VehicleFoo/motorbike.cs',
-    },
+    enabled: false,
+    title: 'motorbike.cs',
+    project: 'example/vehicles',
+    relativePath: '/src/VehicleFoo/motorbike.cs',
   },
-  type: CONTEXT_ITEM_TYPE_PROJECT_FILE,
 };
 const mockFiles = [
   MOCK_CONTEXT_ITEM_FILE,
   {
     id: '223e4567-e89b-12d3-a456-426614174001',
-    isEnabled: true,
+    category: CONTEXT_ITEM_CATEGORY_FILE,
     metadata: {
-      name: 'potato.ts',
-      info: {
-        project: 'example/garden',
-        relFilePath: '/src/plants/potato.ts',
-      },
+      enabled: true,
+      title: 'potato.ts',
+      project: 'example/garden',
+      relativePath: '/src/plants/potato.ts',
     },
-    type: CONTEXT_ITEM_TYPE_PROJECT_FILE,
   },
   MOCK_CONTEXT_ITEM_FILE_DISABLED,
 ];
 
 export const MOCK_CONTEXT_ITEM_ISSUE = {
   id: '423e4567-e89b-12d3-a456-426614174003',
-  isEnabled: true,
+  category: CONTEXT_ITEM_CATEGORY_ISSUE,
   metadata: {
-    name: 'Implement watering schedule',
-    info: {
-      project: 'example/garden',
-      iid: 1234,
-    },
+    enabled: true,
+    title: 'Implement watering schedule',
+    project: 'example/garden',
+    iid: 1234,
   },
-  type: CONTEXT_ITEM_TYPE_ISSUE,
 };
 export const MOCK_CONTEXT_ITEM_ISSUE_DISABLED = {
   id: 'c463fb31-2a4c-4f8e-a609-97230ac48ae5',
-  isEnabled: false,
+  category: CONTEXT_ITEM_CATEGORY_ISSUE,
+
   metadata: {
-    name: `Fix vehicle colours and make them look real nice and colourful won't that be wonderful wow this issue title is really long I sure hope it's gonna wrap OK`,
-    info: {
-      project: 'example/vehicle',
-      iid: 91011,
-    },
+    enabled: false,
+    disabledReasons: ['This foo is not available to bar', 'Lorem something something wow?'],
+    title: `Fix vehicle colours and make them look real nice and colourful won't that be wonderful wow this issue title is really long I sure hope it's gonna wrap OK`,
+    project: 'example/vehicle',
+    iid: 91011,
   },
-  disabledReasons: ['This foo is not available to bar', 'Lorem something something wow?'],
-  type: CONTEXT_ITEM_TYPE_ISSUE,
 };
 
 const mockIssues = [
   MOCK_CONTEXT_ITEM_ISSUE,
   {
     id: '523e4567-e89b-12d3-a456-426614174004',
-    isEnabled: true,
+    category: CONTEXT_ITEM_CATEGORY_ISSUE,
     metadata: {
-      name: 'Refactor plant growth rates',
-      info: {
-        project: 'example/garden',
-        iid: 5678,
-      },
+      enabled: true,
+      title: 'Refactor plant growth rates',
+      project: 'example/garden',
+      iid: 5678,
     },
-    type: CONTEXT_ITEM_TYPE_ISSUE,
   },
   MOCK_CONTEXT_ITEM_ISSUE_DISABLED,
 ];
 
 export const MOCK_CONTEXT_ITEM_MERGE_REQUEST = {
   id: '623e4567-e89b-12d3-a456-426614174005',
-  isEnabled: true,
+  category: CONTEXT_ITEM_CATEGORY_MERGE_REQUEST,
   metadata: {
-    name: 'Improve database performance',
-    info: {
-      project: 'example/garden',
-      iid: 1122,
-    },
+    enabled: true,
+    title: 'Improve database performance',
+    project: 'example/garden',
+    iid: 1122,
   },
-  type: CONTEXT_ITEM_TYPE_MERGE_REQUEST,
 };
 export const MOCK_CONTEXT_ITEM_MERGE_REQUEST_DISABLED = {
   id: '4eb665fc-e5e1-49b0-9789-2a16964e461a',
-  isEnabled: false,
+  category: CONTEXT_ITEM_CATEGORY_MERGE_REQUEST,
   metadata: {
-    name: 'Fix broken layout at small viewports',
-    info: {
-      project: 'example/vehicle',
-      iid: 5566,
-    },
+    enabled: false,
+    disabledReasons: ['This foo is not available to bar', 'Lorem something something wow?'],
+    title: 'Fix broken layout at small viewports',
+    project: 'example/vehicle',
+    iid: 5566,
   },
-  disabledReasons: ['This foo is not available to bar', 'Lorem something something wow?'],
-  type: CONTEXT_ITEM_TYPE_MERGE_REQUEST,
 };
 
 const mockMergeRequests = [
   MOCK_CONTEXT_ITEM_MERGE_REQUEST,
   {
     id: '723e4567-e89b-12d3-a456-426614174006',
-    isEnabled: false,
+    category: CONTEXT_ITEM_CATEGORY_MERGE_REQUEST,
     metadata: {
-      name: 'Add vehicle registration details',
-      info: {
-        project: 'example/vehicle',
-        iid: 3344,
-      },
+      enabled: false,
+      disabledReasons: ['This foo is not available to bar', 'Lorem something something wow?'],
+      title: 'Add vehicle registration details',
+      project: 'example/vehicle',
+      iid: 3344,
     },
-    disabledReasons: ['This foo is not available to bar', 'Lorem something something wow?'],
-    type: CONTEXT_ITEM_TYPE_MERGE_REQUEST,
   },
   MOCK_CONTEXT_ITEM_MERGE_REQUEST_DISABLED,
 ];
@@ -147,7 +130,7 @@ export const getMockContextItems = () => {
   const allItems = [...mockFiles, ...mockIssues, ...mockMergeRequests];
 
   // put disabled items in the back
-  const disabledItems = allItems.filter((item) => !item.isEnabled);
-  const enabledItems = allItems.filter((item) => item.isEnabled);
+  const disabledItems = allItems.filter((item) => !item.metadata.enabled);
+  const enabledItems = allItems.filter((item) => item.metadata.enabled);
   return [...enabledItems, ...disabledItems];
 };
diff --git a/src/components/experimental/duo/chat/components/duo_chat_context/utils.js b/src/components/experimental/duo/chat/components/duo_chat_context/utils.js
index a016d62da8e3a1d08c624698530d2e6c35852cea..1652163dbdc37130cd1a27233963b634531780b1 100644
--- a/src/components/experimental/duo/chat/components/duo_chat_context/utils.js
+++ b/src/components/experimental/duo/chat/components/duo_chat_context/utils.js
@@ -18,9 +18,11 @@ export function contextItemValidator(item) {
   return Boolean(
     item &&
       item.id &&
-      item.type &&
-      typeof item.isEnabled === 'boolean' &&
-      disabledReasonsValidator(item.disabledReasons)
+      item.category &&
+      item.metadata &&
+      typeof item.metadata === 'object' &&
+      typeof item.metadata.enabled === 'boolean' &&
+      disabledReasonsValidator(item.metadata.disabledReasons)
   );
 }
 
diff --git a/src/components/experimental/duo/chat/components/duo_chat_context/utils.spec.js b/src/components/experimental/duo/chat/components/duo_chat_context/utils.spec.js
index 398c07db7799415ce83ae07344a5c0f2713e61b3..b680badf9218d0353ddc6b30cf8b029c7c7b068a 100644
--- a/src/components/experimental/duo/chat/components/duo_chat_context/utils.spec.js
+++ b/src/components/experimental/duo/chat/components/duo_chat_context/utils.spec.js
@@ -90,34 +90,50 @@ describe('duo_chat_context utils', () => {
         description: 'missing id',
       },
       {
-        value: { ...MOCK_CONTEXT_ITEM_FILE, type: undefined },
-        description: 'missing type',
+        value: { ...MOCK_CONTEXT_ITEM_FILE, category: undefined },
+        description: 'missing category',
+      },
+      {
+        value: { ...MOCK_CONTEXT_ITEM_FILE, metadata: undefined },
+        description: 'missing metadata',
       },
       {
         value: {
           ...MOCK_CONTEXT_ITEM_FILE,
-          isEnabled: undefined,
+          metadata: {
+            ...MOCK_CONTEXT_ITEM_FILE.metadata,
+            enabled: undefined,
+          },
         },
         description: 'missing enabled',
       },
       {
         value: {
           ...MOCK_CONTEXT_ITEM_FILE,
-          isEnabled: 'true',
+          metadata: {
+            ...MOCK_CONTEXT_ITEM_FILE.metadata,
+            enabled: 'true',
+          },
         },
         description: 'non-boolean enabled',
       },
       {
         value: {
           ...MOCK_CONTEXT_ITEM_FILE,
-          disabledReasons: 'not an array',
+          metadata: {
+            ...MOCK_CONTEXT_ITEM_FILE.metadata,
+            disabledReasons: 'not an array',
+          },
         },
         description: 'non-array disabledReasons',
       },
       {
         value: {
           ...MOCK_CONTEXT_ITEM_FILE,
-          disabledReasons: [42],
+          metadata: {
+            ...MOCK_CONTEXT_ITEM_FILE.metadata,
+            disabledReasons: [42],
+          },
         },
         description: 'non-string items in disabledReasons array',
       },
@@ -148,23 +164,71 @@ describe('duo_chat_context utils', () => {
     describe.each([
       { value: null, description: 'null' },
       { value: undefined, description: 'undefined' },
-      { value: {}, description: 'object instead of array' },
-      { value: 'not an array', description: 'string instead of array' },
+      { value: {}, description: 'empty object' },
+      { value: 'not an item', description: 'string instead of array' },
       { value: 42, description: 'number instead of array' },
       {
-        value: [{ id: '1', metadata: { name: 'Item 1' } }],
-        description: 'array with item missing isEnabled',
+        value: [{ ...MOCK_CONTEXT_ITEM_FILE, id: undefined }],
+        description: 'missing id',
+      },
+      {
+        value: [{ ...MOCK_CONTEXT_ITEM_FILE, category: undefined }],
+        description: 'missing category',
+      },
+      {
+        value: [{ ...MOCK_CONTEXT_ITEM_FILE, metadata: undefined }],
+        description: 'missing metadata',
       },
       {
-        value: [{ metadata: { name: 'Item 1' }, isEnabled: true }],
-        description: 'array with item missing id',
+        value: [
+          {
+            ...MOCK_CONTEXT_ITEM_FILE,
+            metadata: {
+              ...MOCK_CONTEXT_ITEM_FILE.metadata,
+              enabled: undefined,
+            },
+          },
+        ],
+        description: 'missing enabled',
+      },
+      {
+        value: [
+          {
+            ...MOCK_CONTEXT_ITEM_FILE,
+            metadata: {
+              ...MOCK_CONTEXT_ITEM_FILE.metadata,
+              enabled: 'true',
+            },
+          },
+        ],
+        description: 'non-boolean enabled',
       },
       {
-        value: [{ id: '1', metadata: { name: 'Item 1' }, isEnabled: 'true' }],
-        description: 'array with item having non-boolean isEnabled',
+        value: [
+          {
+            ...MOCK_CONTEXT_ITEM_FILE,
+            metadata: {
+              ...MOCK_CONTEXT_ITEM_FILE.metadata,
+              disabledReasons: 'not an array',
+            },
+          },
+        ],
+        description: 'non-array disabledReasons',
+      },
+      {
+        value: [
+          {
+            ...MOCK_CONTEXT_ITEM_FILE,
+            metadata: {
+              ...MOCK_CONTEXT_ITEM_FILE.metadata,
+              disabledReasons: [42],
+            },
+          },
+        ],
+        description: 'non-string items in disabledReasons array',
       },
       {
-        value: [MOCK_CONTEXT_ITEM_FILE, { metadata: { name: 'Item 2' }, isEnabled: false }],
+        value: [MOCK_CONTEXT_ITEM_FILE, { id: 1234, invalid: true }],
         description: 'array with one valid and one invalid item',
       },
     ])('with "$description"', ({ value }) => {
diff --git a/src/components/experimental/duo/chat/duo_chat.stories.js b/src/components/experimental/duo/chat/duo_chat.stories.js
index 35819f5d34d19dcfbf8b7983d253e01f807119d4..6b7f0674eeefa45580726e0e81b6053ecdb5b0e2 100644
--- a/src/components/experimental/duo/chat/duo_chat.stories.js
+++ b/src/components/experimental/duo/chat/duo_chat.stories.js
@@ -186,9 +186,9 @@ export const Interactive = (args, { argTypes }) => ({
       setStoryTimeout(() => {
         this.contextItemsLoading = false;
         this.contextItemsResults = sampleContextItems
-          .filter((item) => item.type === category)
+          .filter((item) => item.category === category)
           .filter(
-            (item) => !query || item.metadata.name.toLowerCase().includes(query.toLowerCase())
+            (item) => !query || item.metadata.title.toLowerCase().includes(query.toLowerCase())
           )
           .filter((item) => !this.contextItems.some((contextItem) => contextItem.id === item.id));
       }, 300);