@@ -381,7 +381,8 @@ disables enforcement for every error, not just transient ones.
 Every content item on a message is submitted for evaluation, not just its text: `DataContent` is sent
 as Purview binary content, and `FunctionCallContent`, `FunctionResultContent` and other structured
 content are serialized to text. Only `UsageContent` is skipped, because it carries token counts rather
-than user data.
+than user data. Text annotations such as citations, `ErrorContent.Details` and `DataContent.Name`
+are submitted as additional text entries.
 
 ### Remote references are not dereferenced
 
 
@@ -278,11 +278,39 @@ private static List<ContentBase> MapMessageContents(ChatMessage message)
             {
                 mapped.Add(purviewContent);
             }
+
+            AddSupplementalContent(content, mapped);
         }
 
         return mapped;
     }
 
+    /// <summary>
+    /// Add entries for user or model supplied data that <see cref="MapContent"/> does not carry:
+    /// annotations (for example citations), error details and the name of a data item.
+    /// </summary>
+    private static void AddSupplementalContent(AIContent content, List<ContentBase> mapped)
+    {
+        switch (content)
+        {
+            case TextContent or TextReasoningContent when content.Annotations is { Count: > 0 }:
+                foreach (AIAnnotation annotation in content.Annotations)
+                {
+                    mapped.Add(new PurviewTextContent(JsonSerializer.Serialize(annotation, AIJsonUtilities.DefaultOptions.GetTypeInfo(annotation.GetType()))));
+                }
+
+                break;
+
+            case ErrorContent { Details: { Length: > 0 } details }:
+                mapped.Add(new PurviewTextContent(details));
+                break;
+
+            case DataContent { Name: { Length: > 0 } name }:
+                mapped.Add(new PurviewTextContent(name));
+                break;
+        }
+    }
+
     /// <summary>
     /// Map a single <see cref="AIContent"/> onto a Purview content item.
     /// </summary>
 
@@ -1214,6 +1214,58 @@ await this._processor.ProcessMessagesAsync(
         Assert.NotEqual(binaryEntry.Identifier, functionCallEntry.Identifier);
     }
 
+    /// <summary>
+    /// Verifies annotations, error details and data names are submitted alongside the main payload.
+    /// </summary>
+    [Fact]
+    public async Task ProcessMessagesAsync_WithAnnotationsErrorDetailsAndDataName_SubmitsThemForEvaluationAsync()
+    {
+        // Arrange
+        List<ChatMessage> messages =
+        [
+            new(ChatRole.Assistant,
+            [
+                new TextContent("see sources") { Annotations = [new CitationAnnotation { Title = "cited-title-111", Url = new Uri("https://example.com/cited") }] },
+                new ErrorContent("failed") { Details = "error-details-222" },
+                new DataContent(new byte[] { 1, 2, 3 }, "application/octet-stream") { Name = "file-name-333.bin" },
+                new DataContent(ReadOnlyMemory<byte>.Empty, "application/octet-stream") { Name = "empty-file-name-444.bin" }
+            ])
+        ];
+        PurviewSettings settings = CreateValidPurviewSettings();
+        TokenInfo tokenInfo = new() { TenantId = "tenant-123", UserId = "user-123", ClientId = "client-123" };
+
+        this._mockPurviewClient.Setup(x => x.GetUserInfoFromTokenAsync(It.IsAny<CancellationToken>(), null))
+            .ReturnsAsync(tokenInfo);
+        this._mockCacheProvider.Setup(x => x.GetAsync<ProtectionScopesCacheKey, ProtectionScopesResponse>(
+            It.IsAny<ProtectionScopesCacheKey>(), It.IsAny<CancellationToken>()))
+            .ReturnsAsync(CreateApplicableProtectionScopesResponse());
+
+        List<ProcessContentRequest> capturedRequests = [];
+        this._mockPurviewClient.Setup(x => x.ProcessContentAsync(
+            It.IsAny<ProcessContentRequest>(), It.IsAny<CancellationToken>()))
+            .Callback<ProcessContentRequest, CancellationToken>((request, _) => capturedRequests.Add(request))
+            .ReturnsAsync(new ProcessContentResponse());
+
+        // Act
+        await this._processor.ProcessMessagesAsync(
+            messages, "session-123", Activity.UploadText, settings, "user-123", CancellationToken.None);
+
+        // Assert
+        List<string> texts = [];
+        foreach (ProcessContentRequest request in capturedRequests)
+        {
+            if (request.ContentToProcess.ContentEntries[0].Content is PurviewTextContent text)
+            {
+                texts.Add(text.Data);
+            }
+        }
+
+        Assert.Contains(texts, t => t.Contains("cited-title-111", StringComparison.Ordinal));
+        Assert.Contains("error-details-222", texts);
+        Assert.Contains("file-name-333.bin", texts);
+        Assert.Contains("empty-file-name-444.bin", texts);
+    }
+
     [Fact]
     public async Task ProcessMessagesAsync_WithEmptyTextAndData_SkipsEmptyContentAsync()
     {
 
@@ -468,7 +468,7 @@ disables enforcement for every error, not just transient ones.
 Every content item on a message is submitted for evaluation, not just its text: binary/data content is
 sent as Purview binary content, and function calls, function results and other structured content are
 serialized to text. Only `usage` content is skipped, because it carries token counts rather than user
-data.
+data. Annotations on text content, such as citations, are submitted as additional text entries.
 
 Evaluation covers the response as it stands when the middleware runs. Because middleware can replace
 the response afterwards, what is evaluated depends on where the middleware is attached — see
 
@@ -137,7 +137,14 @@ def _map_content(content: Content) -> ContentBase | None:
 
 def _map_message_contents(message: Message) -> list[ContentBase]:
     """Map every non-empty content item of a message to Purview content entries."""
-    return [purview_content for content in message.contents if (purview_content := _map_content(content))]
+    mapped: list[ContentBase] = []
+    for content in message.contents:
+        if purview_content := _map_content(content):
+            mapped.append(purview_content)
+        # Annotations (for example citations) are not part of the text, so they are evaluated separately.
+        if content.type in ("text", "text_reasoning") and content.annotations:
+            mapped.extend(PurviewTextContent(data=_serialize_for_evaluation(a)) for a in content.annotations)
+    return mapped
 
 
 def _is_blocking_action(action_info: DlpActionInfo) -> bool:
 
@@ -193,6 +193,27 @@ async def test_map_messages_submits_each_content_item_in_separate_request(
         assert all(entry.content is not None for entry in entries)
         assert not any(isinstance(entry.content, PurviewTextContent) and entry.content.data == "" for entry in entries)
 
+    async def test_map_messages_submits_annotations_for_evaluation(self, processor: ScopedContentProcessor) -> None:
+        """Test annotations on text content are submitted in addition to the text."""
+        from agent_framework import Content
+
+        content = Content.from_text(
+            "see sources",
+            annotations=[{"type": "citation", "title": "cited-title-111", "url": "https://example.com/cited"}],
+        )
+        messages = [Message(role="assistant", contents=[content])]
+
+        requests, _ = await processor._map_messages(messages, Activity.UPLOAD_TEXT)
+
+        texts = [
+            entry.content.data
+            for r in requests
+            for entry in r.content_to_process.content_entries
+            if isinstance(entry.content, PurviewTextContent)
+        ]
+        assert "see sources" in texts
+        assert any("cited-title-111" in text for text in texts)
+
     async def test_map_messages_skips_empty_text_and_data(self, processor: ScopedContentProcessor) -> None:
         """Test _map_messages does not create requests for empty text or binary data."""
         from agent_framework import Content