diff --git a/browser/ui/webui/ai_chat/ai_chat_ui_page_handler.cc b/browser/ui/webui/ai_chat/ai_chat_ui_page_handler.cc
index 505df5a78a74..a6ce4cbfc680 100644
--- a/browser/ui/webui/ai_chat/ai_chat_ui_page_handler.cc
+++ b/browser/ui/webui/ai_chat/ai_chat_ui_page_handler.cc
@@ -273,10 +273,9 @@ void AIChatUIPageHandler::BindParentUIFrameFromChildFrame(
 
 void AIChatUIPageHandler::GetFaviconImageDataForAssociatedContent(
     GetFaviconImageDataCallback callback,
-    mojom::SiteInfoPtr content_info,
+    mojom::AssociatedContentPtr content_info,
     bool should_send_page_contents) {
-  if (!content_info->is_content_association_possible ||
-      !content_info->url.has_value() || !content_info->url->is_valid()) {
+  if (!content_info || !content_info->url.is_valid()) {
     std::move(callback).Run(std::nullopt);
     return;
   }
@@ -297,7 +296,7 @@ void AIChatUIPageHandler::GetFaviconImageDataForAssociatedContent(
       };
 
   favicon_service_->GetRawFaviconForPageURL(
-      content_info->url.value(), icon_types, kDesiredFaviconSizePixels, true,
+      content_info->url, icon_types, kDesiredFaviconSizePixels, true,
       base::BindOnce(on_favicon_available, std::move(callback)),
       &favicon_task_tracker_);
 }
diff --git a/browser/ui/webui/ai_chat/ai_chat_ui_page_handler.h b/browser/ui/webui/ai_chat/ai_chat_ui_page_handler.h
index a8fa5d418829..e695b8e5a3b6 100644
--- a/browser/ui/webui/ai_chat/ai_chat_ui_page_handler.h
+++ b/browser/ui/webui/ai_chat/ai_chat_ui_page_handler.h
@@ -90,7 +90,7 @@ class AIChatUIPageHandler : public mojom::AIChatUIHandler,
 
   void GetFaviconImageDataForAssociatedContent(
       GetFaviconImageDataCallback callback,
-      mojom::SiteInfoPtr content_info,
+      mojom::AssociatedContentPtr content_info,
       bool should_send_page_contents);
 
   raw_ptr<AIChatTabHelper> active_chat_tab_helper_ = nullptr;
diff --git a/components/ai_chat/core/browser/ai_chat_database.cc b/components/ai_chat/core/browser/ai_chat_database.cc
index dbe97c31c9da..3dd30f10caf4 100644
--- a/components/ai_chat/core/browser/ai_chat_database.cc
+++ b/components/ai_chat/core/browser/ai_chat_database.cc
@@ -194,14 +194,12 @@ std::vector<mojom::ConversationPtr> AIChatDatabase::GetAllConversations() {
     conversation->updated_time = statement.ColumnTime(index++);
     conversation->has_content = true;
 
-    conversation->associated_content = mojom::SiteInfo::New();
-
     if (statement.GetColumnType(index) != sql::ColumnType::kNull) {
       DVLOG(1) << __func__ << " got associated content";
-
+      conversation->associated_content = mojom::AssociatedContent::New();
       conversation->associated_content->uuid = statement.ColumnString(index++);
       conversation->associated_content->title =
-          DecryptOptionalColumnToString(statement, index++);
+          DecryptOptionalColumnToString(statement, index++).value_or("");
       auto url_raw = DecryptOptionalColumnToString(statement, index++);
       if (url_raw.has_value()) {
         conversation->associated_content->url = GURL(url_raw.value());
@@ -212,9 +210,6 @@ std::vector<mojom::ConversationPtr> AIChatDatabase::GetAllConversations() {
           statement.ColumnInt(index++);
       conversation->associated_content->is_content_refined =
           statement.ColumnBool(index++);
-      conversation->associated_content->is_content_association_possible = true;
-    } else {
-      conversation->associated_content->is_content_association_possible = false;
     }
   }
 
@@ -426,10 +421,10 @@ bool AIChatDatabase::AddConversation(mojom::ConversationPtr conversation,
     return false;
   }
 
-  if (conversation->associated_content->is_content_association_possible) {
+  if (conversation->associated_content) {
     DVLOG(2) << "Adding associated content for conversation "
              << conversation->uuid << " with url "
-             << conversation->associated_content->url->spec();
+             << conversation->associated_content->url.spec();
     if (!AddOrUpdateAssociatedContent(
             conversation->uuid, std::move(conversation->associated_content),
             contents)) {
@@ -452,7 +447,7 @@ bool AIChatDatabase::AddConversation(mojom::ConversationPtr conversation,
 
 bool AIChatDatabase::AddOrUpdateAssociatedContent(
     std::string_view conversation_uuid,
-    mojom::SiteInfoPtr associated_content,
+    mojom::AssociatedContentPtr associated_content,
     std::optional<std::string> contents) {
   DCHECK_CALLED_ON_VALID_SEQUENCE(sequence_checker_);
   if (!LazyInit()) {
@@ -461,7 +456,7 @@ bool AIChatDatabase::AddOrUpdateAssociatedContent(
 
   // TODO(petemill): handle multiple associated content per conversation
   CHECK(!conversation_uuid.empty());
-  CHECK(associated_content->uuid.has_value());
+  CHECK(associated_content);
 
   // Check if we already have persisted this content
   static constexpr char kSelectExistingAssociatedContentId[] =
@@ -471,13 +466,12 @@ bool AIChatDatabase::AddOrUpdateAssociatedContent(
       SQL_FROM_HERE, kSelectExistingAssociatedContentId));
   CHECK(select_statement.is_valid());
   select_statement.BindString(0, conversation_uuid);
-  select_statement.BindString(1, associated_content->uuid.value());
+  select_statement.BindString(1, associated_content->uuid);
 
   sql::Statement statement;
   if (select_statement.Step()) {
     DVLOG(4) << "Updating associated content for conversation "
-             << conversation_uuid << " with id "
-             << associated_content->uuid.value();
+             << conversation_uuid << " with id " << associated_content->uuid;
     static constexpr char kUpdateAssociatedContentQuery[] =
         "UPDATE associated_content"
         " SET title = ?,"
@@ -502,13 +496,13 @@ bool AIChatDatabase::AddOrUpdateAssociatedContent(
   int index = 0;
   BindAndEncryptOptionalString(statement, index++, associated_content->title);
   BindAndEncryptOptionalString(statement, index++,
-                               associated_content->url->spec());
+                               associated_content->url.spec());
   statement.BindInt(index++,
                     base::to_underlying(associated_content->content_type));
   BindAndEncryptOptionalString(statement, index++, contents);
   statement.BindInt(index++, associated_content->content_used_percentage);
   statement.BindBool(index++, associated_content->is_content_refined);
-  statement.BindString(index++, associated_content->uuid.value());
+  statement.BindString(index++, associated_content->uuid);
   statement.BindString(index, conversation_uuid);
 
   if (!statement.Run()) {
@@ -1016,9 +1010,8 @@ bool AIChatDatabase::CreateSchema() {
       "title BLOB,"
       // Encrypted url string
       "url BLOB,"
-      // Stores SiteInfo.IsVideo. Future-proofed for multiple content types
-      // 0 for regular content
-      // 1 for video.
+      // Stores AssociatedContent.IsVideo. Future-proofed for multiple content
+      // types 0 for regular content 1 for video.
       "content_type INTEGER NOT NULL,"
       // Encrypted string value of the content, so that conversations can be
       // continued.
diff --git a/components/ai_chat/core/browser/ai_chat_database.h b/components/ai_chat/core/browser/ai_chat_database.h
index 96b3cac36f41..b1dedf9136ce 100644
--- a/components/ai_chat/core/browser/ai_chat_database.h
+++ b/components/ai_chat/core/browser/ai_chat_database.h
@@ -50,9 +50,10 @@ class AIChatDatabase {
                        mojom::ConversationTurnPtr first_entry);
 
   // Update any properties of associated content metadata or full-text content
-  bool AddOrUpdateAssociatedContent(std::string_view conversation_uuid,
-                                    mojom::SiteInfoPtr associated_content,
-                                    std::optional<std::string> content);
+  bool AddOrUpdateAssociatedContent(
+      std::string_view conversation_uuid,
+      mojom::AssociatedContentPtr associated_content,
+      std::optional<std::string> content);
 
   // Adds a new conversation entry to the conversation with the provided UUID
   bool AddConversationEntry(
diff --git a/components/ai_chat/core/browser/ai_chat_database_unittest.cc b/components/ai_chat/core/browser/ai_chat_database_unittest.cc
index 88a3b4582528..203d62023ca7 100644
--- a/components/ai_chat/core/browser/ai_chat_database_unittest.cc
+++ b/components/ai_chat/core/browser/ai_chat_database_unittest.cc
@@ -126,14 +126,11 @@ TEST_P(AIChatDatabaseTest, AddAndGetConversationAndEntries) {
     // recent entry.
     const GURL page_url = GURL("https://example.com/page");
     const std::string expected_contents = "Page contents";
-    mojom::SiteInfoPtr associated_content =
-        has_content
-            ? mojom::SiteInfo::New(
-                  content_uuid, mojom::ContentType::PageContent, "page title",
-                  page_url.host(), page_url, 62, true, true)
-            : mojom::SiteInfo::New(
-                  std::nullopt, mojom::ContentType::PageContent, std::nullopt,
-                  std::nullopt, std::nullopt, 0, false, false);
+    mojom::AssociatedContentPtr associated_content =
+        has_content ? mojom::AssociatedContent::New(
+                          content_uuid, mojom::ContentType::PageContent,
+                          "page title", page_url, 62, true)
+                    : nullptr;
     const mojom::ConversationPtr metadata =
         mojom::Conversation::New(uuid, "title", now - base::Hours(2), true,
                                  std::nullopt, std::move(associated_content));
@@ -265,10 +262,7 @@ TEST_P(AIChatDatabaseTest, UpdateConversationTitle) {
         base::StrCat({"for_conversation_title_", initial_title});
     const std::string updated_title = "updated title";
     mojom::ConversationPtr metadata = mojom::Conversation::New(
-        uuid, initial_title, base::Time::Now(), true, std::nullopt,
-        mojom::SiteInfo::New(std::nullopt, mojom::ContentType::PageContent,
-                             std::nullopt, std::nullopt, std::nullopt, 0, false,
-                             false));
+        uuid, initial_title, base::Time::Now(), true, std::nullopt, nullptr);
 
     // Persist the first entry (and get the response ready)
     const auto history = CreateSampleChatHistory(1u);
@@ -298,9 +292,9 @@ TEST_P(AIChatDatabaseTest, AddOrUpdateAssociatedContent) {
   const GURL page_url = GURL("https://example.com/page");
   mojom::ConversationPtr metadata = mojom::Conversation::New(
       uuid, "title", base::Time::Now() - base::Hours(2), true, std::nullopt,
-      mojom::SiteInfo::New(content_uuid, mojom::ContentType::PageContent,
-                           "page title", page_url.host(), page_url, 62, true,
-                           true));
+      mojom::AssociatedContent::New(content_uuid,
+                                    mojom::ContentType::PageContent,
+                                    "page title", page_url, 62, true));
 
   auto history = CreateSampleChatHistory(1u);
 
@@ -329,7 +323,7 @@ TEST_P(AIChatDatabaseTest, AddOrUpdateAssociatedContent) {
   result = db_->GetConversationData(uuid);
   EXPECT_EQ(result->associated_content.size(), 1u);
   EXPECT_EQ(result->associated_content[0]->content_uuid,
-            metadata->associated_content->uuid.value());
+            metadata->associated_content->uuid);
   EXPECT_EQ(result->associated_content[0]->content, expected_contents);
   conversations = db_->GetAllConversations();
   EXPECT_EQ(conversations.size(), 1u);
@@ -341,9 +335,7 @@ TEST_P(AIChatDatabaseTest, DeleteAllData) {
   const GURL page_url = GURL("https://example.com/page");
   mojom::ConversationPtr metadata = mojom::Conversation::New(
       uuid, "title", base::Time::Now() - base::Hours(2), true, std::nullopt,
-      mojom::SiteInfo::New(std::nullopt, mojom::ContentType::PageContent,
-                           std::nullopt, std::nullopt, std::nullopt, 0, false,
-                           false));
+      nullptr);
 
   auto history = CreateSampleChatHistory(1u);
 
@@ -380,14 +372,14 @@ TEST_P(AIChatDatabaseTest, DeleteAssociatedWebContent) {
   // are persisted.
   mojom::ConversationPtr metadata_first = mojom::Conversation::New(
       "first", "title", base::Time::Now() - base::Hours(2), true, std::nullopt,
-      mojom::SiteInfo::New("first-content", mojom::ContentType::PageContent,
-                           "page title", page_url.host(), page_url, 62, true,
-                           true));
+      mojom::AssociatedContent::New("first-content",
+                                    mojom::ContentType::PageContent,
+                                    "page title", page_url, 62, true));
   mojom::ConversationPtr metadata_second = mojom::Conversation::New(
       "second", "title", base::Time::Now() - base::Hours(1), true, "model-2",
-      mojom::SiteInfo::New("second-content", mojom::ContentType::PageContent,
-                           "page title", page_url.host(), page_url, 62, true,
-                           true));
+      mojom::AssociatedContent::New("second-content",
+                                    mojom::ContentType::PageContent,
+                                    "page title", page_url, 62, true));
 
   auto history_first = CreateSampleChatHistory(1u, -2);
   auto history_second = CreateSampleChatHistory(1u, -1);
@@ -427,8 +419,8 @@ TEST_P(AIChatDatabaseTest, DeleteAssociatedWebContent) {
   conversations = db_->GetAllConversations();
   EXPECT_EQ(conversations.size(), 2u);
   ExpectConversationEquals(FROM_HERE, conversations[0], metadata_first);
-  metadata_second->associated_content->url = std::nullopt;
-  metadata_second->associated_content->title = std::nullopt;
+  metadata_second->associated_content->url = GURL();
+  metadata_second->associated_content->title = "";
   ExpectConversationEquals(FROM_HERE, conversations[1], metadata_second);
 
   archive_result = db_->GetConversationData("second");
@@ -540,12 +532,8 @@ TEST_P(AIChatDatabaseMigrationTest, MigrationToVCurrent) {
     // ConversationEntry table changed, check it persists correctly
     auto now = base::Time::Now();
     const std::string uuid = "migrationtest";
-    mojom::SiteInfoPtr associated_content = mojom::SiteInfo::New(
-        std::nullopt, mojom::ContentType::PageContent, std::nullopt,
-        std::nullopt, std::nullopt, 0, false, false);
-    const mojom::ConversationPtr metadata =
-        mojom::Conversation::New(uuid, "title", now - base::Hours(2), true,
-                                 std::nullopt, std::move(associated_content));
+    const mojom::ConversationPtr metadata = mojom::Conversation::New(
+        uuid, "title", now - base::Hours(2), true, std::nullopt, nullptr);
 
     // Persist the first entry (and get the response ready)
     auto history = CreateSampleChatHistory(1u);
diff --git a/components/ai_chat/core/browser/ai_chat_service.cc b/components/ai_chat/core/browser/ai_chat_service.cc
index b4d449e50d90..3dd9c70b97de 100644
--- a/components/ai_chat/core/browser/ai_chat_service.cc
+++ b/components/ai_chat/core/browser/ai_chat_service.cc
@@ -157,10 +157,7 @@ ConversationHandler* AIChatService::CreateConversation() {
   // Create the conversation metadata
   {
     mojom::ConversationPtr conversation = mojom::Conversation::New(
-        conversation_uuid, "", base::Time::Now(), false, std::nullopt,
-        mojom::SiteInfo::New(base::Uuid::GenerateRandomV4().AsLowercaseString(),
-                             mojom::ContentType::PageContent, std::nullopt,
-                             std::nullopt, std::nullopt, 0, false, false));
+        conversation_uuid, "", base::Time::Now(), false, std::nullopt, nullptr);
     conversations_.insert_or_assign(conversation_uuid, std::move(conversation));
   }
   mojom::Conversation* conversation =
@@ -745,7 +742,7 @@ void AIChatService::HandleFirstEntry(
   DVLOG(1) << __func__ << " Conversation " << conversation->uuid
            << " being persisted for first time.";
   CHECK(entry->uuid.has_value());
-  CHECK(conversation->associated_content->uuid.has_value());
+
   // We can persist the conversation metadata for the first time as well as the
   // entry.
   if (ai_chat_db_) {
@@ -780,7 +777,7 @@ void AIChatService::HandleNewEntry(
                   conversation->model_key, std::nullopt);
 
     if (associated_content_value.has_value() &&
-        conversation->associated_content->is_content_association_possible) {
+        conversation->associated_content) {
       ai_chat_db_
           .AsyncCall(
               base::IgnoreResult(&AIChatDatabase::AddOrUpdateAssociatedContent))
diff --git a/components/ai_chat/core/browser/ai_chat_service_unittest.cc b/components/ai_chat/core/browser/ai_chat_service_unittest.cc
index 60e464b31d4d..d2bab71bb902 100644
--- a/components/ai_chat/core/browser/ai_chat_service_unittest.cc
+++ b/components/ai_chat/core/browser/ai_chat_service_unittest.cc
@@ -113,7 +113,6 @@ class MockConversationHandlerClient : public mojom::ConversationUI {
     conversation_ui_receiver_.reset();
   }
 
-
   MOCK_METHOD(void, OnConversationHistoryUpdate, (), (override));
 
   MOCK_METHOD(void, OnAPIRequestInProgress, (bool), (override));
@@ -133,7 +132,7 @@ class MockConversationHandlerClient : public mojom::ConversationUI {
 
   MOCK_METHOD(void,
               OnAssociatedContentInfoChanged,
-              (const mojom::SiteInfoPtr, bool),
+              (const mojom::AssociatedContentPtr, bool),
               (override));
 
   MOCK_METHOD(void, OnFaviconImageDataChanged, (), (override));
@@ -496,10 +495,10 @@ TEST_P(AIChatServiceUnitTest, GetOrCreateConversationHandlerForContent) {
   base::RunLoop run_loop;
   conversation_with_content->GetAssociatedContentInfo(
       base::BindLambdaForTesting(
-          [&](mojom::SiteInfoPtr site_info, bool should_send_page_contents) {
-            EXPECT_TRUE(site_info->is_content_association_possible);
-            EXPECT_TRUE(site_info->url.has_value());
-            EXPECT_EQ(site_info->url.value(), GURL("https://example.com"));
+          [&](mojom::AssociatedContentPtr associated_content,
+              bool should_send_page_contents) {
+            EXPECT_TRUE(associated_content);
+            EXPECT_EQ(associated_content->url, GURL("https://example.com"));
             run_loop.Quit();
           }));
   run_loop.Run();
@@ -558,10 +557,10 @@ TEST_P(AIChatServiceUnitTest,
   base::RunLoop run_loop;
   conversation_with_content->GetAssociatedContentInfo(
       base::BindLambdaForTesting(
-          [&](mojom::SiteInfoPtr site_info, bool should_send_page_contents) {
+          [&](mojom::AssociatedContentPtr associated_content,
+              bool should_send_page_contents) {
             EXPECT_FALSE(should_send_page_contents);
-            EXPECT_FALSE(site_info->is_content_association_possible);
-            EXPECT_FALSE(site_info->url.has_value());
+            EXPECT_FALSE(associated_content);
             run_loop.Quit();
           }));
   run_loop.Run();
@@ -814,13 +813,12 @@ TEST_P(AIChatServiceUnitTest, DeleteAssociatedWebContent) {
     // Verify associated are initially correct
     base::RunLoop run_loop;
     data[i].conversation_handler->GetAssociatedContentInfo(
-        base::BindLambdaForTesting([&](mojom::SiteInfoPtr site_info,
+        base::BindLambdaForTesting([&](mojom::AssociatedContentPtr site_info,
                                        bool should_send_page_contents) {
           SCOPED_TRACE(testing::Message() << "data index: " << i);
-          EXPECT_TRUE(site_info->is_content_association_possible);
-          EXPECT_TRUE(site_info->url.has_value());
-          EXPECT_EQ(site_info->url.value(), content_url);
-          EXPECT_EQ(site_info->title.value(), base::UTF16ToUTF8(page_title));
+          ASSERT_TRUE(site_info);
+          EXPECT_EQ(site_info->url, content_url);
+          EXPECT_EQ(site_info->title, base::UTF16ToUTF8(page_title));
           run_loop.Quit();
         }));
     run_loop.Run();
@@ -849,18 +847,16 @@ TEST_P(AIChatServiceUnitTest, DeleteAssociatedWebContent) {
   for (int i = 0; i < 3; i++) {
     base::RunLoop run_loop;
     data[i].conversation_handler->GetAssociatedContentInfo(
-        base::BindLambdaForTesting([&](mojom::SiteInfoPtr site_info,
+        base::BindLambdaForTesting([&](mojom::AssociatedContentPtr site_info,
                                        bool should_send_page_contents) {
           SCOPED_TRACE(testing::Message() << "data index: " << i);
-          EXPECT_TRUE(site_info->is_content_association_possible);
-          EXPECT_TRUE(site_info->url.has_value());
-          EXPECT_TRUE(site_info->title.has_value());
+          ASSERT_TRUE(site_info);
           if (i == 1) {
-            EXPECT_TRUE(site_info->url->is_empty());
-            EXPECT_TRUE(site_info->title->empty());
+            EXPECT_TRUE(site_info->url.is_empty());
+            EXPECT_TRUE(site_info->title.empty());
           } else {
-            EXPECT_EQ(site_info->url.value(), content_url);
-            EXPECT_EQ(site_info->title.value(), base::UTF16ToUTF8(page_title));
+            EXPECT_EQ(site_info->url, content_url);
+            EXPECT_EQ(site_info->title, base::UTF16ToUTF8(page_title));
           }
           run_loop.Quit();
         }));
diff --git a/components/ai_chat/core/browser/conversation_handler.cc b/components/ai_chat/core/browser/conversation_handler.cc
index a74530bbd762..d797d92e663d 100644
--- a/components/ai_chat/core/browser/conversation_handler.cc
+++ b/components/ai_chat/core/browser/conversation_handler.cc
@@ -229,9 +229,9 @@ ConversationHandler::ConversationHandler(
     mojom::ConversationArchivePtr conversation_data =
         std::move(initial_state.value());
     if (!conversation_data->associated_content.empty()) {
-      CHECK(metadata_->associated_content->uuid.has_value());
+      CHECK(metadata_->associated_content);
       CHECK_EQ(conversation_data->associated_content[0]->content_uuid,
-               metadata_->associated_content->uuid.value());
+               metadata_->associated_content->uuid);
       bool is_video = (metadata_->associated_content->content_type ==
                        mojom::ContentType::VideoTranscript);
       SetArchiveContent(conversation_data->associated_content[0]->content,
@@ -289,14 +289,20 @@ void ConversationHandler::BindUntrustedConversationUI(
 }
 
 void ConversationHandler::OnConversationMetadataUpdated() {
-  // Pass the updated data to archive content
   if (archive_content_) {
-    archive_content_->SetMetadata(
-        metadata_->associated_content->url.value_or(GURL()),
-        base::UTF8ToUTF16(metadata_->associated_content->title.value_or("")),
-        metadata_->associated_content->content_type ==
-            mojom::ContentType::VideoTranscript);
+    if (metadata_->associated_content) {
+      // Pass the updated data to archive content
+      archive_content_->SetMetadata(
+          metadata_->associated_content->url,
+          base::UTF8ToUTF16(metadata_->associated_content->title),
+          metadata_->associated_content->content_type ==
+              mojom::ContentType::VideoTranscript);
+    } else {
+      // TODO: Confirm with @petemill if this is the correct behavior
+      archive_content_->SetMetadata(GURL(), u"", false);
+    }
   }
+
   // Notify UI. If we have live content then the metadata will be updated
   // again from that live data.
   OnAssociatedContentInfoChanged();
@@ -411,8 +417,7 @@ void ConversationHandler::OnAssociatedContentDestroyed(
                         : -1;
   DisassociateContentDelegate();
   if (!chat_history_.empty() && should_send_page_contents_ &&
-      metadata_->associated_content &&
-      metadata_->associated_content->is_content_association_possible) {
+      metadata_->associated_content) {
     // Get the latest version of article text and
     // associated_content_info_ if this chat has history and was connected to
     // the associated conversation, then store the content so the conversation
@@ -428,13 +433,13 @@ void ConversationHandler::OnAssociatedContentDestroyed(
 
 void ConversationHandler::SetArchiveContent(std::string text_content,
                                             bool is_video) {
+  CHECK(metadata_->associated_content);
+
   // Construct a "content archive" implementation of AssociatedContentDelegate
   // with a duplicate of the article text.
   auto archive_content = std::make_unique<AssociatedArchiveContent>(
-      metadata_->associated_content->url.value_or(GURL()),
-      std::move(text_content),
-      base::UTF8ToUTF16(metadata_->associated_content->title.value_or("")),
-      is_video);
+      metadata_->associated_content->url, std::move(text_content),
+      base::UTF8ToUTF16(metadata_->associated_content->title), is_video);
   associated_content_delegate_ = archive_content->GetWeakPtr();
   archive_content_ = std::move(archive_content);
   should_send_page_contents_ = features::IsPageContextEnabledInitially();
@@ -518,8 +523,9 @@ void ConversationHandler::GetState(GetStateCallback callback) {
   mojom::ConversationStatePtr state = mojom::ConversationState::New(
       metadata_->uuid, is_request_in_progress_, std::move(models_copy),
       model_key, std::move(suggestions), suggestion_generation_status_,
-      metadata_->associated_content->Clone(), should_send_page_contents_,
-      current_error_);
+      metadata_->associated_content ? metadata_->associated_content->Clone()
+                                    : nullptr,
+      should_send_page_contents_, current_error_);
 
   std::move(callback).Run(std::move(state));
 }
@@ -968,7 +974,9 @@ void ConversationHandler::DisassociateContentDelegate() {
 void ConversationHandler::GetAssociatedContentInfo(
     GetAssociatedContentInfoCallback callback) {
   BuildAssociatedContentInfo();
-  std::move(callback).Run(metadata_->associated_content->Clone(),
+  std::move(callback).Run(metadata_->associated_content
+                              ? metadata_->associated_content->Clone()
+                              : nullptr,
                           should_send_page_contents_);
 }
 
@@ -1429,9 +1437,11 @@ void ConversationHandler::OnGeneratePageContentComplete(
   is_content_different_ =
       is_content_different_ || contents_text != previous_content;
 
-  metadata_->associated_content->content_type =
-      is_video ? mojom::ContentType::VideoTranscript
-               : mojom::ContentType::PageContent;
+  if (metadata_->associated_content) {
+    metadata_->associated_content->content_type =
+        is_video ? mojom::ContentType::VideoTranscript
+                 : mojom::ContentType::PageContent;
+  }
 
   std::move(callback).Run(contents_text, is_video, invalidation_token);
 
@@ -1671,20 +1681,25 @@ bool ConversationHandler::IsContentAssociationPossible() {
 void ConversationHandler::BuildAssociatedContentInfo() {
   // Only modify associated content metadata here
   if (associated_content_delegate_) {
+    // Note: We don't create a new AssociatedContent object here unless one
+    // doesn't exist. If we generate one with a new UUID the deserializer
+    // breaks.
+    if (!metadata_->associated_content) {
+      metadata_->associated_content = mojom::AssociatedContent::New();
+      metadata_->associated_content->uuid =
+          base::Uuid::GenerateRandomV4().AsLowercaseString();
+      LOG(ERROR) << "Created new AssociatedContent "
+                 << metadata_->associated_content->uuid;
+    }
     metadata_->associated_content->title =
         base::UTF16ToUTF8(associated_content_delegate_->GetTitle());
     const GURL url = associated_content_delegate_->GetURL();
-    metadata_->associated_content->hostname = url.host();
     metadata_->associated_content->url = url;
     metadata_->associated_content->content_used_percentage =
         GetContentUsedPercentage();
     metadata_->associated_content->is_content_refined = is_content_refined_;
-    metadata_->associated_content->is_content_association_possible = true;
   } else {
-    metadata_->associated_content->title = std::nullopt;
-    metadata_->associated_content->hostname = std::nullopt;
-    metadata_->associated_content->url = std::nullopt;
-    metadata_->associated_content->is_content_association_possible = false;
+    metadata_->associated_content = nullptr;
   }
 }
 
@@ -1699,7 +1714,7 @@ ConversationHandler::GetStateForConversationEntries() {
   entries_state->is_content_refined = is_content_refined_;
   entries_state->is_leo_model = is_leo_model;
   entries_state->content_used_percentage =
-      metadata_->associated_content->is_content_association_possible
+      metadata_->associated_content
           ? std::make_optional(
                 metadata_->associated_content->content_used_percentage)
           : std::nullopt;
@@ -1716,7 +1731,9 @@ void ConversationHandler::OnAssociatedContentInfoChanged() {
   BuildAssociatedContentInfo();
   for (auto& client : conversation_ui_handlers_) {
     client->OnAssociatedContentInfoChanged(
-        metadata_->associated_content->Clone(), should_send_page_contents_);
+        metadata_->associated_content ? metadata_->associated_content->Clone()
+                                      : nullptr,
+        should_send_page_contents_);
   }
   OnStateForConversationEntriesChanged();
 }
diff --git a/components/ai_chat/core/browser/conversation_handler_unittest.cc b/components/ai_chat/core/browser/conversation_handler_unittest.cc
index 8766416f8993..64faac51260b 100644
--- a/components/ai_chat/core/browser/conversation_handler_unittest.cc
+++ b/components/ai_chat/core/browser/conversation_handler_unittest.cc
@@ -38,7 +38,6 @@
 #include "brave/components/ai_chat/core/browser/types.h"
 #include "brave/components/ai_chat/core/browser/utils.h"
 #include "brave/components/ai_chat/core/common/features.h"
-#include "brave/components/ai_chat/core/common/mojom/ai_chat.mojom-shared.h"
 #include "brave/components/ai_chat/core/common/mojom/ai_chat.mojom.h"
 #include "brave/components/ai_chat/core/common/pref_names.h"
 #include "components/grit/brave_components_strings.h"
@@ -109,7 +108,7 @@ class MockConversationHandlerClient : public mojom::ConversationUI {
 
   MOCK_METHOD(void,
               OnAssociatedContentInfoChanged,
-              (const mojom::SiteInfoPtr, bool),
+              (const mojom::AssociatedContentPtr, bool),
               (override));
 
   MOCK_METHOD(void, OnFaviconImageDataChanged, (), (override));
@@ -207,12 +206,8 @@ class ConversationHandlerUnitTest : public testing::Test {
         os_crypt_.get(), shared_url_loader_factory_, "",
         temp_directory_.GetPath());
 
-    mojom::SiteInfoPtr non_content = mojom::SiteInfo::New(
-        std::nullopt, mojom::ContentType::PageContent, std::nullopt,
-        std::nullopt, std::nullopt, 0, false, false);
-    conversation_ =
-        mojom::Conversation::New("uuid", "title", base::Time::Now(), false,
-                                 std::nullopt, std::move(non_content));
+    conversation_ = mojom::Conversation::New("uuid", "title", base::Time::Now(),
+                                             false, std::nullopt, nullptr);
 
     conversation_handler_ = std::make_unique<ConversationHandler>(
         conversation_.get(), ai_chat_service_.get(), model_service_.get(),
@@ -375,8 +370,7 @@ TEST_F(ConversationHandlerUnitTest, GetState) {
                     should_send_content
                         ? mojom::SuggestionGenerationStatus::CanGenerate
                         : mojom::SuggestionGenerationStatus::None);
-          EXPECT_TRUE(
-              state->associated_content_info->is_content_association_possible);
+          EXPECT_TRUE(state->associated_content);
           EXPECT_EQ(state->should_send_content, should_send_content);
           EXPECT_EQ(state->error, mojom::APIError::None);
           run_loop.Quit();
@@ -410,13 +404,15 @@ TEST_F(ConversationHandlerUnitTest, SubmitSelectedText) {
   EXPECT_FALSE(conversation_handler_->HasAnyHistory());
 
   // Test without page contents.
-  conversation_handler_->GetAssociatedContentInfo(base::BindLambdaForTesting(
-      [&](mojom::SiteInfoPtr site_info, bool should_send_page_contents) {
+  conversation_handler_->GetAssociatedContentInfo(
+      base::BindLambdaForTesting([&](mojom::AssociatedContentPtr site_info,
+                                     bool should_send_page_contents) {
         EXPECT_TRUE(should_send_page_contents);
       }));
   conversation_handler_->SetShouldSendPageContents(false);
-  conversation_handler_->GetAssociatedContentInfo(base::BindLambdaForTesting(
-      [&](mojom::SiteInfoPtr site_info, bool should_send_page_contents) {
+  conversation_handler_->GetAssociatedContentInfo(
+      base::BindLambdaForTesting([&](mojom::AssociatedContentPtr site_info,
+                                     bool should_send_page_contents) {
         EXPECT_FALSE(should_send_page_contents);
       }));
 
@@ -448,12 +444,13 @@ TEST_F(ConversationHandlerUnitTest, SubmitSelectedText) {
   testing::Mock::VerifyAndClearExpectations(associated_content_.get());
   // article_text_ and suggestions_ should be cleared when page content is
   // unlinked.
-  conversation_handler_->GetAssociatedContentInfo(base::BindLambdaForTesting(
-      [&](mojom::SiteInfoPtr site_info, bool should_send_page_contents) {
+  conversation_handler_->GetAssociatedContentInfo(
+      base::BindLambdaForTesting([&](mojom::AssociatedContentPtr site_info,
+                                     bool should_send_page_contents) {
         EXPECT_FALSE(should_send_page_contents);
         // We should not have any relationship to associated content
         // once conversation history is committed.
-        EXPECT_FALSE(site_info->is_content_association_possible);
+        EXPECT_FALSE(site_info);
       }));
   EXPECT_TRUE(conversation_handler_->GetSuggestedQuestionsForTest().empty());
 
@@ -506,11 +503,12 @@ TEST_F(ConversationHandlerUnitTest, SubmitSelectedText_WithAssociatedContent) {
   EXPECT_CALL(*associated_content_, GetContent)
       .WillOnce(base::test::RunOnceCallback<0>(page_content, false, ""));
   conversation_handler_->SetShouldSendPageContents(true);
-  conversation_handler_->GetAssociatedContentInfo(base::BindLambdaForTesting(
-      [&](mojom::SiteInfoPtr site_info, bool should_send_page_contents) {
+  conversation_handler_->GetAssociatedContentInfo(
+      base::BindLambdaForTesting([&](mojom::AssociatedContentPtr site_info,
+                                     bool should_send_page_contents) {
         EXPECT_TRUE(should_send_page_contents);
-        EXPECT_TRUE(site_info->is_content_association_possible);
-        EXPECT_EQ(site_info->url->spec(), "https://www.brave.com/");
+        ASSERT_TRUE(site_info);
+        EXPECT_EQ(site_info->url, GURL("https://www.brave.com/"));
       }));
 
   NiceMock<MockConversationHandlerClient> client(conversation_handler_.get());
@@ -533,11 +531,12 @@ TEST_F(ConversationHandlerUnitTest, SubmitSelectedText_WithAssociatedContent) {
   testing::Mock::VerifyAndClearExpectations(&client);
 
   // associated info should be unchanged
-  conversation_handler_->GetAssociatedContentInfo(base::BindLambdaForTesting(
-      [&](mojom::SiteInfoPtr site_info, bool should_send_page_contents) {
+  conversation_handler_->GetAssociatedContentInfo(
+      base::BindLambdaForTesting([&](mojom::AssociatedContentPtr site_info,
+                                     bool should_send_page_contents) {
         EXPECT_TRUE(should_send_page_contents);
-        EXPECT_TRUE(site_info->is_content_association_possible);
-        EXPECT_EQ(site_info->url->spec(), "https://www.brave.com/");
+        ASSERT_TRUE(site_info);
+        EXPECT_EQ(site_info->url, GURL("https://www.brave.com/"));
       }));
 
   // Should not be any LLM-generated suggested questions yet because they
@@ -944,8 +943,9 @@ TEST_F(ConversationHandlerUnitTest,
   // History update notification once for each entry
   EXPECT_CALL(client, OnConversationHistoryUpdate()).Times(2);
 
-  conversation_handler_->GetAssociatedContentInfo(base::BindLambdaForTesting(
-      [&](mojom::SiteInfoPtr site_info, bool should_send_page_contents) {
+  conversation_handler_->GetAssociatedContentInfo(
+      base::BindLambdaForTesting([&](mojom::AssociatedContentPtr site_info,
+                                     bool should_send_page_contents) {
         EXPECT_TRUE(should_send_page_contents);
       }));
 
@@ -1005,8 +1005,9 @@ TEST_F(ConversationHandlerUnitTest,
   NiceMock<MockConversationHandlerClient> client(conversation_handler_.get());
   EXPECT_CALL(client, OnConversationHistoryUpdate()).Times(4);
   EXPECT_TRUE(conversation_handler_->IsAnyClientConnected());
-  conversation_handler_->GetAssociatedContentInfo(base::BindLambdaForTesting(
-      [&](mojom::SiteInfoPtr site_info, bool should_send_page_contents) {
+  conversation_handler_->GetAssociatedContentInfo(
+      base::BindLambdaForTesting([&](mojom::AssociatedContentPtr site_info,
+                                     bool should_send_page_contents) {
         EXPECT_TRUE(should_send_page_contents);
       }));
 
@@ -1201,8 +1202,9 @@ TEST_F(ConversationHandlerUnitTest,
   // Connecting a client will trigger content staging.
   NiceMock<MockConversationHandlerClient> client(conversation_handler_.get());
   EXPECT_TRUE(conversation_handler_->IsAnyClientConnected());
-  conversation_handler_->GetAssociatedContentInfo(base::BindLambdaForTesting(
-      [&](mojom::SiteInfoPtr site_info, bool should_send_page_contents) {
+  conversation_handler_->GetAssociatedContentInfo(
+      base::BindLambdaForTesting([&](mojom::AssociatedContentPtr site_info,
+                                     bool should_send_page_contents) {
         EXPECT_TRUE(should_send_page_contents);
       }));
 
@@ -1219,9 +1221,10 @@ TEST_F(ConversationHandlerUnitTest,
   // use page content.
   SetAssociatedContentStagedEntries(/*empty=*/false);
   conversation_handler_->SetShouldSendPageContents(false);
-  conversation_handler_->GetAssociatedContentInfo(base::BindLambdaForTesting(
-      [&](mojom::SiteInfoPtr site_info, bool should_send_page_contents) {
-        EXPECT_TRUE(site_info->is_content_association_possible);
+  conversation_handler_->GetAssociatedContentInfo(
+      base::BindLambdaForTesting([&](mojom::AssociatedContentPtr site_info,
+                                     bool should_send_page_contents) {
+        EXPECT_TRUE(site_info);
         EXPECT_FALSE(should_send_page_contents);
       }));
 
@@ -1241,9 +1244,8 @@ TEST_F(ConversationHandlerUnitTest_NoAssociatedContent,
        MaybeFetchOrClearSearchQuerySummary) {
   // Ensure nothing gets staged when there's no associated content.
   conversation_handler_->GetAssociatedContentInfo(base::BindLambdaForTesting(
-      [&](mojom::SiteInfoPtr site_info, bool should_send_page_contents) {
-        EXPECT_FALSE(site_info->is_content_association_possible);
-      }));
+      [&](mojom::AssociatedContentPtr site_info,
+          bool should_send_page_contents) { EXPECT_FALSE(site_info); }));
   // Client connecting would trigger content staging
   NiceMock<MockConversationHandlerClient> client(conversation_handler_.get());
   EXPECT_CALL(client, OnConversationHistoryUpdate()).Times(0);
@@ -1379,8 +1381,9 @@ TEST_F(ConversationHandlerUnitTest, SubmitSuggestion) {
 
 TEST_F(ConversationHandlerUnitTest, GenerateQuestions_DisableSendPageContent) {
   conversation_handler_->SetShouldSendPageContents(false);
-  conversation_handler_->GetAssociatedContentInfo(base::BindLambdaForTesting(
-      [&](mojom::SiteInfoPtr site_info, bool should_send_page_contents) {
+  conversation_handler_->GetAssociatedContentInfo(
+      base::BindLambdaForTesting([&](mojom::AssociatedContentPtr site_info,
+                                     bool should_send_page_contents) {
         EXPECT_FALSE(should_send_page_contents);
       }));
   EXPECT_CALL(*associated_content_, GetURL).Times(0);
diff --git a/components/ai_chat/core/browser/test_utils.cc b/components/ai_chat/core/browser/test_utils.cc
index c7b1ced131e7..94887a9f8172 100644
--- a/components/ai_chat/core/browser/test_utils.cc
+++ b/components/ai_chat/core/browser/test_utils.cc
@@ -73,8 +73,8 @@ void ExpectConversationEquals(base::Location location,
 }
 
 void ExpectAssociatedContentEquals(base::Location location,
-                                   const mojom::SiteInfoPtr& a,
-                                   const mojom::SiteInfoPtr& b) {
+                                   const mojom::AssociatedContentPtr& a,
+                                   const mojom::AssociatedContentPtr& b) {
   SCOPED_TRACE(testing::Message() << location.ToString());
   if (!a || !b) {
     EXPECT_EQ(a, b);  // Both should be null or neither
@@ -86,8 +86,6 @@ void ExpectAssociatedContentEquals(base::Location location,
   EXPECT_EQ(a->content_type, b->content_type);
   EXPECT_EQ(a->content_used_percentage, b->content_used_percentage);
   EXPECT_EQ(a->is_content_refined, b->is_content_refined);
-  EXPECT_EQ(a->is_content_association_possible,
-            b->is_content_association_possible);
 }
 
 void ExpectConversationHistoryEquals(
diff --git a/components/ai_chat/core/browser/test_utils.h b/components/ai_chat/core/browser/test_utils.h
index a56716508e91..984c0fb9999a 100644
--- a/components/ai_chat/core/browser/test_utils.h
+++ b/components/ai_chat/core/browser/test_utils.h
@@ -19,8 +19,8 @@ void ExpectConversationEquals(base::Location location,
                               const mojom::ConversationPtr& b);
 
 void ExpectAssociatedContentEquals(base::Location location,
-                                   const mojom::SiteInfoPtr& a,
-                                   const mojom::SiteInfoPtr& b);
+                                   const mojom::AssociatedContentPtr& a,
+                                   const mojom::AssociatedContentPtr& b);
 
 void ExpectConversationEntryEquals(base::Location location,
                                    const mojom::ConversationTurnPtr& a,
diff --git a/components/ai_chat/core/common/mojom/ai_chat.mojom b/components/ai_chat/core/common/mojom/ai_chat.mojom
index 7b6769d375bd..9ab214aa31c9 100644
--- a/components/ai_chat/core/common/mojom/ai_chat.mojom
+++ b/components/ai_chat/core/common/mojom/ai_chat.mojom
@@ -74,29 +74,20 @@ enum ContentType {
   VideoTranscript,
 };
 
-// A piece of content associated with a conversation.
-// TODO(petemill): Rename to AssociatedContent and have hostname/url/title be
-// part of a detail property (which would have different structure possibilities
-// depending on content type.
-struct SiteInfo {
-  string? uuid;
+// Represents the content that is associated with a conversation.
+struct AssociatedContent {
+  string uuid;
+
   ContentType content_type;
-  // Web page specific fields, if available and allowed
-  string? title;
-  string? hostname;
-  url.mojom.Url? url;
+  string title;
+  url.mojom.Url url;
 
   // Percentage of the content that has been utilized by remote LLM (0-100)
   int32 content_used_percentage;
+
   // Indicates content has been refined through extracting most relevant parts
   // from long page content
   bool is_content_refined;
-
-  // Indicates if the URL scheme is of a type that allows for
-  // content association.
-  // TODO(petemill): SiteInfo should just not exist if content-associated is
-  // not possible.
-  bool is_content_association_possible;
 };
 
 struct Conversation {
@@ -110,7 +101,7 @@ struct Conversation {
   // Model key, if different than default
   string? model_key;
 
-  SiteInfo associated_content;
+  AssociatedContent? associated_content;
 };
 
 struct ContentArchive {
@@ -413,7 +404,7 @@ struct ConversationState {
   string current_model_key;
   array<string> suggested_questions;
   SuggestionGenerationStatus suggestion_status;
-  SiteInfo associated_content_info;
+  AssociatedContent? associated_content;
   bool should_send_content;
   APIError error;
   // TODO(petemill): include conversation history, once
@@ -467,11 +458,11 @@ interface ConversationHandler {
   // the assistant.
   SubmitSuggestion(string suggestion);
 
-  // Get associated page information. If there is none then |site_info| will be
-  // |null|. If the reason for that is it's still being fetched, then
+  // Get associated page information. If there is none then |associated_content|
+  // will be |null|. If the reason for that is it's still being fetched, then
   // |is_fetching| will be |true|.
   GetAssociatedContentInfo() => (
-      SiteInfo associated_content_info, bool should_send_content);
+      AssociatedContent? associated_content, bool should_send_content);
 
   SetShouldSendPageContents(bool should_send);
 
@@ -537,10 +528,10 @@ interface ConversationUI {
   // Browser window.
   OnSuggestedQuestionsChanged(
       array<string> questions, SuggestionGenerationStatus status);
-  // Associated page information has changed. If there is none then |site_info|
+  // Associated page information has changed. If there is none then |associated_content|
   // will be |null|. If the reason for that is it's still being fetched, then
   // |is_fetching| will be |true|.
-  OnAssociatedContentInfoChanged(SiteInfo info, bool should_send_page_contents);
+  OnAssociatedContentInfoChanged(AssociatedContent? associated_content, bool should_send_page_contents);
   OnFaviconImageDataChanged();
   OnConversationDeleted();
 };
diff --git a/components/ai_chat/resources/page/components/feedback_form/index.tsx b/components/ai_chat/resources/page/components/feedback_form/index.tsx
index 3e578cad09f8..ecb8e5e0ed21 100644
--- a/components/ai_chat/resources/page/components/feedback_form/index.tsx
+++ b/components/ai_chat/resources/page/components/feedback_form/index.tsx
@@ -84,13 +84,13 @@ function FeedbackForm() {
             />
           </label>
         </fieldset>
-        {conversationContext.associatedContentInfo?.hostname && (
+        {conversationContext.associatedContentInfo && (
           <fieldset>
             <Checkbox checked={shouldSendUrl} onChange={handleCheckboxChange}>
               <label>{
                 formatMessage(getLocale('sendSiteHostnameLabel'), {
                   placeholders: {
-                    $1: conversationContext.associatedContentInfo.hostname
+                    $1: new URL(conversationContext.associatedContentInfo.url.url).hostname
                   }
                 })
               }</label>
diff --git a/components/ai_chat/resources/page/components/main/index.tsx b/components/ai_chat/resources/page/components/main/index.tsx
index 973117915d3f..0715ad9872cb 100644
--- a/components/ai_chat/resources/page/components/main/index.tsx
+++ b/components/ai_chat/resources/page/components/main/index.tsx
@@ -72,7 +72,7 @@ function Main() {
     !conversationContext.apiHasError && // Don't show premium prompt and errors (rate limit error has its own premium prompt suggestion)
     !shouldShowStorageNotice && // Don't show premium prompt and storage notice
     aiChatContext.canShowPremiumPrompt &&
-    conversationContext.associatedContentInfo === null && // SiteInfo request has finished and this is a standalone conversation
+    conversationContext.associatedContentInfo === null && // AssociatedContent request has finished and this is a standalone conversation
     !aiChatContext.isPremiumUser
 
 
@@ -82,7 +82,7 @@ function Main() {
   const showContextToggle =
     (conversationContext.conversationHistory.length === 0 ||
       isLastTurnBraveSearchSERPSummary) &&
-    conversationContext.associatedContentInfo?.isContentAssociationPossible
+    !!conversationContext.associatedContentInfo
 
   let currentErrorElement = null
 
@@ -253,7 +253,7 @@ function Main() {
             <>
               <ModelIntro />
 
-              {conversationContext.associatedContentInfo?.isContentAssociationPossible && conversationContext.shouldSendPageContents && (
+              {conversationContext.associatedContentInfo && conversationContext.shouldSendPageContents && (
                 <div className={styles.siteTitleContainer}>
                   <SiteTitle size='default' />
                 </div>
diff --git a/components/ai_chat/resources/page/components/welcome_guide/index.tsx b/components/ai_chat/resources/page/components/welcome_guide/index.tsx
index 78e47a5a25a3..7c903f87468a 100644
--- a/components/ai_chat/resources/page/components/welcome_guide/index.tsx
+++ b/components/ai_chat/resources/page/components/welcome_guide/index.tsx
@@ -26,7 +26,7 @@ function WelcomeGuide() {
         <h4 className={styles.cardTitle}>
           {getLocale('welcomeGuideSiteHelpCardTitle')}
         </h4>
-        {conversationContext.associatedContentInfo?.isContentAssociationPossible &&
+        {conversationContext.associatedContentInfo &&
         conversationContext.shouldSendPageContents ? (
           <>
             <p>{getLocale('welcomeGuideSiteHelpCardDescWithAction')}</p>
diff --git a/components/ai_chat/resources/page/state/conversation_context.tsx b/components/ai_chat/resources/page/state/conversation_context.tsx
index d6d81be07b41..0dcd2c4f7042 100644
--- a/components/ai_chat/resources/page/state/conversation_context.tsx
+++ b/components/ai_chat/resources/page/state/conversation_context.tsx
@@ -25,7 +25,7 @@ export interface CharCountContext {
 export type ConversationContext = SendFeedbackState & CharCountContext & {
   conversationUuid?: string
   conversationHistory: Mojom.ConversationTurn[]
-  associatedContentInfo?: Mojom.SiteInfo
+  associatedContentInfo?: Mojom.AssociatedContent
   allModels: Mojom.Model[]
   currentModel?: Mojom.Model
   suggestedQuestions: string[]
@@ -201,7 +201,7 @@ export function ConversationContextProvider(props: React.PropsWithChildren) {
         currentModelKey,
         suggestedQuestions,
         suggestionStatus,
-        associatedContentInfo,
+        associatedContent,
         shouldSendContent,
         error
       } } = await conversationHandler.getState()
@@ -211,7 +211,7 @@ export function ConversationContextProvider(props: React.PropsWithChildren) {
         ...getModelContext(currentModelKey, models),
         suggestedQuestions,
         suggestionStatus,
-        associatedContentInfo,
+        associatedContentInfo: associatedContent,
         shouldSendPageContents: shouldSendContent,
         currentError: error
       })
@@ -260,7 +260,7 @@ export function ConversationContextProvider(props: React.PropsWithChildren) {
 
     id = callbackRouter.onAssociatedContentInfoChanged.addListener(
       (
-        associatedContentInfo: Mojom.SiteInfo,
+        associatedContentInfo: Mojom.AssociatedContent,
         shouldSendPageContents: boolean
       ) => {
         setPartialContext({
diff --git a/components/ai_chat/resources/page/stories/components_panel.tsx b/components/ai_chat/resources/page/stories/components_panel.tsx
index 0f1466bbbf28..90d95bb7f75d 100644
--- a/components/ai_chat/resources/page/stories/components_panel.tsx
+++ b/components/ai_chat/resources/page/stories/components_panel.tsx
@@ -76,24 +76,13 @@ function getPageContentRefineEvent(): Mojom.ConversationEntryEvent {
   }
 }
 
-const associatedContentNone: Mojom.SiteInfo =  {
-  uuid: undefined,
-  contentType: Mojom.ContentType.PageContent,
-  isContentAssociationPossible: false,
-  contentUsedPercentage: 0,
-  isContentRefined: false,
-  title: undefined,
-  hostname: undefined,
-  url: undefined,
-}
-
 const CONVERSATIONS: Mojom.Conversation[] = [
   {
     title: 'Star Trek Poem',
     uuid: '1',
     hasContent: true,
     updatedTime: { internalValue: BigInt('13278618001000000') },
-    associatedContent: associatedContentNone,
+    associatedContent: undefined,
     modelKey: undefined,
   },
   {
@@ -101,7 +90,7 @@ const CONVERSATIONS: Mojom.Conversation[] = [
     uuid: '2',
     hasContent: true,
     updatedTime: { internalValue: BigInt('13278618001000001') },
-    associatedContent: associatedContentNone,
+    associatedContent: undefined,
     modelKey: undefined,
   },
   {
@@ -109,7 +98,7 @@ const CONVERSATIONS: Mojom.Conversation[] = [
     uuid: '3',
     hasContent: true,
     updatedTime: { internalValue: BigInt('13278618001000002') },
-    associatedContent: associatedContentNone,
+    associatedContent: undefined,
     modelKey: undefined,
   }
 ]
@@ -388,13 +377,11 @@ const SAMPLE_QUESTIONS = [
   'Why did google executives disregard this character in the company?'
 ]
 
-const SITE_INFO: Mojom.SiteInfo = {
-  uuid: undefined,
+const ASSOCIATED_CONTENT: Mojom.AssociatedContent = {
+  uuid: 'uuid',
   contentType: Mojom.ContentType.PageContent,
   title: 'Tiny Tweaks to Neurons Can Rewire Animal Motion',
   contentUsedPercentage: 40,
-  isContentAssociationPossible: true,
-  hostname: 'www.example.com',
   url: { url: 'https://www.example.com/a' },
   isContentRefined: false,
 }
@@ -409,7 +396,7 @@ type CustomArgs = {
   deletingConversationId: string | null
   visibleConversationListCount: number
   hasSuggestedQuestions: boolean
-  hasSiteInfo: boolean
+  hasAssociatedContent: boolean
   isFeedbackFormVisible: boolean
   isStorageNoticeDismissed: boolean
   canShowPremiumPrompt: boolean
@@ -435,7 +422,7 @@ const args: CustomArgs = {
   hasConversation: true,
   visibleConversationListCount: CONVERSATIONS.length,
   hasSuggestedQuestions: true,
-  hasSiteInfo: true,
+  hasAssociatedContent: true,
   editingConversationId: null,
   deletingConversationId: null,
   isFeedbackFormVisible: false,
@@ -505,10 +492,10 @@ function StoryContext(props: React.PropsWithChildren<{args: CustomArgs, setArgs:
   const options = { args: props.args }
   const { setArgs } = props
 
-  const siteInfo = options.args.hasSiteInfo ? SITE_INFO : new Mojom.SiteInfo()
+  const associatedContent = options.args.hasAssociatedContent ? ASSOCIATED_CONTENT : new Mojom.AssociatedContent()
   const suggestedQuestions = options.args.hasSuggestedQuestions
     ? SAMPLE_QUESTIONS
-    : siteInfo
+    : associatedContent
       ? [SAMPLE_QUESTIONS[0]]
       : []
 
@@ -578,7 +565,7 @@ function StoryContext(props: React.PropsWithChildren<{args: CustomArgs, setArgs:
   const conversationContext: ConversationContext = {
     conversationUuid: CONVERSATIONS[1].uuid,
     conversationHistory: options.args.hasConversation ? HISTORY : [],
-    associatedContentInfo: siteInfo,
+    associatedContentInfo: associatedContent,
     allModels: MODELS,
     currentModel,
     suggestedQuestions,
@@ -590,7 +577,7 @@ function StoryContext(props: React.PropsWithChildren<{args: CustomArgs, setArgs:
     shouldDisableUserInput: false,
     shouldShowLongPageWarning: options.args.shouldShowLongPageWarning,
     shouldShowLongConversationInfo: options.args.shouldShowLongConversationInfo,
-    shouldSendPageContents: siteInfo?.isContentAssociationPossible,
+    shouldSendPageContents: !!associatedContent,
     inputText,
     actionList: ACTIONS_LIST,
     selectedActionType: undefined,
diff --git a/ios/brave-ios/Sources/AIChat/ModelView/AIChatViewModel.swift b/ios/brave-ios/Sources/AIChat/ModelView/AIChatViewModel.swift
index 2bf12e63a463..eefb6bf7dbba 100644
--- a/ios/brave-ios/Sources/AIChat/ModelView/AIChatViewModel.swift
+++ b/ios/brave-ios/Sources/AIChat/ModelView/AIChatViewModel.swift
@@ -27,7 +27,7 @@ public class AIChatViewModel: NSObject, ObservableObject {
   private let braveTalkScript: AIChatBraveTalkJavascript?
   var querySubmited: String?
 
-  @Published var siteInfo: AiChat.SiteInfo?
+  @Published var siteInfo: AiChat.AssociatedContent?
   @Published var _shouldSendPageContents: Bool = true
   @Published var _canShowPremiumPrompt: Bool = false
   @Published var premiumStatus: AiChat.PremiumStatus = .inactive
@@ -194,7 +194,7 @@ public class AIChatViewModel: NSObject, ObservableObject {
     self.requestInProgress = state.isRequestInProgress
     self.suggestedQuestions = state.suggestedQuestions
     self.suggestionsStatus = state.suggestionStatus
-    self.siteInfo = state.associatedContentInfo
+    self.siteInfo = state.associatedContent
     self._shouldSendPageContents = state.shouldSendContent
     self.apiError = state.error
     self.models = state.allModels
@@ -327,7 +327,7 @@ extension AIChatViewModel: AIChatDelegate {
   }
 
   public func onPageHasContent(
-    _ siteInfo: AiChat.SiteInfo,
+    _ siteInfo: AiChat.AssociatedContent,
     shouldSendContent shouldSendPageContents: Bool
   ) {
     self.siteInfo = siteInfo
diff --git a/ios/browser/api/ai_chat/ai_chat_delegate.h b/ios/browser/api/ai_chat/ai_chat_delegate.h
index fbc2569c150b..cc0f49e317f5 100644
--- a/ios/browser/api/ai_chat/ai_chat_delegate.h
+++ b/ios/browser/api/ai_chat/ai_chat_delegate.h
@@ -26,7 +26,7 @@ OBJC_EXPORT
              modelList:(NSArray<AiChatModel*>*)modelList;
 - (void)onSuggestedQuestionsChanged:(NSArray<NSString*>*)questions
                              status:(AiChatSuggestionGenerationStatus)status;
-- (void)onPageHasContent:(AiChatSiteInfo*)siteInfo
+- (void)onPageHasContent:(AiChatAssociatedContent*)siteInfo
        shouldSendContent:(bool)shouldSendContent;
 - (void)onServiceStateChanged:(AiChatServiceState*)state;
 @end
diff --git a/ios/browser/api/ai_chat/conversation_client.h b/ios/browser/api/ai_chat/conversation_client.h
index 7ec3051dc317..7967e577d8e5 100644
--- a/ios/browser/api/ai_chat/conversation_client.h
+++ b/ios/browser/api/ai_chat/conversation_client.h
@@ -43,8 +43,9 @@ class ConversationClient : public mojom::ConversationUI,
   void OnSuggestedQuestionsChanged(
       const std::vector<std::string>& questions,
       mojom::SuggestionGenerationStatus status) override;
-  void OnAssociatedContentInfoChanged(const mojom::SiteInfoPtr site_info,
-                                      bool should_send_content) override;
+  void OnAssociatedContentInfoChanged(
+      const mojom::AssociatedContentPtr site_info,
+      bool should_send_content) override;
   void OnFaviconImageDataChanged() override;
   void OnConversationDeleted() override;
 
diff --git a/ios/browser/api/ai_chat/conversation_client.mm b/ios/browser/api/ai_chat/conversation_client.mm
index d51bfdb2bb1a..f234097c2aca 100644
--- a/ios/browser/api/ai_chat/conversation_client.mm
+++ b/ios/browser/api/ai_chat/conversation_client.mm
@@ -69,10 +69,10 @@
 }
 
 void ConversationClient::OnAssociatedContentInfoChanged(
-    const mojom::SiteInfoPtr site_info,
+    const mojom::AssociatedContentPtr site_info,
     bool should_send_content) {
-  [bridge_ onPageHasContent:[[AiChatSiteInfo alloc]
-                                initWithSiteInfoPtr:site_info->Clone()]
+  [bridge_ onPageHasContent:[[AiChatAssociatedContent alloc]
+                                initWithAssociatedContentPtr:site_info->Clone()]
           shouldSendContent:should_send_content];
 }