diff --git a/lib/pangea/choreographer/controllers/igc_controller.dart b/lib/pangea/choreographer/controllers/igc_controller.dart
index ab0e48669..237697b40 100644
--- a/lib/pangea/choreographer/controllers/igc_controller.dart
+++ b/lib/pangea/choreographer/controllers/igc_controller.dart
@@ -4,12 +4,14 @@ import 'dart:developer';
 import 'package:fluffychat/pangea/choreographer/controllers/choreographer.dart';
 import 'package:fluffychat/pangea/choreographer/controllers/error_service.dart';
 import 'package:fluffychat/pangea/choreographer/controllers/span_data_controller.dart';
+import 'package:fluffychat/pangea/matrix_event_wrappers/pangea_message_event.dart';
 import 'package:fluffychat/pangea/models/igc_text_data_model.dart';
 import 'package:fluffychat/pangea/models/pangea_match_model.dart';
 import 'package:fluffychat/pangea/repo/igc_repo.dart';
 import 'package:fluffychat/pangea/widgets/igc/span_card.dart';
 import 'package:flutter/foundation.dart';
 import 'package:flutter/material.dart';
+import 'package:matrix/matrix.dart';
 
 import '../../models/span_card_model.dart';
 import '../../utils/error_handler.dart';
@@ -43,6 +45,7 @@ class IgcController {
         userL2: choreographer.l2LangCode!,
         enableIGC: choreographer.igcEnabled && !onlyTokensAndLanguageDetection,
         enableIT: choreographer.itEnabled && !onlyTokensAndLanguageDetection,
+        prevMessages: prevMessages(),
       );
 
       final IGCTextData igcTextDataResponse = await IgcRepo.getIGC(
@@ -125,6 +128,49 @@ class IgcController {
     );
   }
 
+  /// Get the content of previous text and audio messages in chat.
+  /// Passed to IGC request to add context.
+  List<PreviousMessage> prevMessages({int numMessages = 5}) {
+    final List<Event> events = choreographer.chatController.visibleEvents
+        .where(
+          (e) =>
+              e.type == EventTypes.Message &&
+              (e.messageType == MessageTypes.Text ||
+                  e.messageType == MessageTypes.Audio),
+        )
+        .toList();
+
+    final List<PreviousMessage> messages = [];
+    for (final Event event in events) {
+      final String? content = event.messageType == MessageTypes.Text
+          ? event.content.toString()
+          : PangeaMessageEvent(
+              event: event,
+              timeline: choreographer.chatController.timeline!,
+              ownMessage: event.senderId ==
+                  choreographer.pangeaController.matrixState.client.userID,
+            )
+              .getSpeechToTextLocal(
+                choreographer.l1LangCode,
+                choreographer.l2LangCode,
+              )
+              ?.transcript
+              .text;
+      if (content == null) continue;
+      messages.add(
+        PreviousMessage(
+          content: content,
+          sender: event.senderId,
+          timestamp: event.originServerTs,
+        ),
+      );
+      if (messages.length >= numMessages) {
+        return messages;
+      }
+    }
+    return messages;
+  }
+
   bool get hasRelevantIGCTextData {
     if (igcTextData == null) return false;
 
diff --git a/lib/pangea/constants/model_keys.dart b/lib/pangea/constants/model_keys.dart
index b42061446..195e919b4 100644
--- a/lib/pangea/constants/model_keys.dart
+++ b/lib/pangea/constants/model_keys.dart
@@ -69,6 +69,10 @@ class ModelKey {
   static const String permissions = "permissions";
   static const String enableIGC = "enable_igc";
   static const String enableIT = "enable_it";
+  static const String prevMessages = "prev_messages";
+  static const String prevContent = "prev_content";
+  static const String prevSender = "prev_sender";
+  static const String prevTimestamp = "prev_timestamp";
 
   static const String originalSent = "original_sent";
   static const String originalWritten = "original_written";
diff --git a/lib/pangea/matrix_event_wrappers/pangea_message_event.dart b/lib/pangea/matrix_event_wrappers/pangea_message_event.dart
index f1c9e5082..cd4ce5e76 100644
--- a/lib/pangea/matrix_event_wrappers/pangea_message_event.dart
+++ b/lib/pangea/matrix_event_wrappers/pangea_message_event.dart
@@ -269,6 +269,21 @@ class PangeaMessageEvent {
             null;
       }).toSet();
 
+  SpeechToTextModel? getSpeechToTextLocal(
+    String? l1Code,
+    String? l2Code,
+  ) {
+    if (l1Code == null || l2Code == null) {
+      return null;
+    }
+    return representations
+        .firstWhereOrNull(
+          (element) => element.content.speechToText != null,
+        )
+        ?.content
+        .speechToText;
+  }
+
   Future<SpeechToTextModel?> getSpeechToText(
     String l1Code,
     String l2Code,
diff --git a/lib/pangea/repo/igc_repo.dart b/lib/pangea/repo/igc_repo.dart
index e32f6cab7..33abb4deb 100644
--- a/lib/pangea/repo/igc_repo.dart
+++ b/lib/pangea/repo/igc_repo.dart
@@ -94,12 +94,42 @@ class IgcRepo {
   }
 }
 
+/// Previous text/audio message sent in chat
+/// Contain message content, sender, and timestamp
+class PreviousMessage {
+  String content;
+  String sender;
+  DateTime timestamp;
+
+  PreviousMessage({
+    required this.content,
+    required this.sender,
+    required this.timestamp,
+  });
+
+  factory PreviousMessage.fromJson(Map<String, dynamic> json) =>
+      PreviousMessage(
+        content: json[ModelKey.prevContent] ?? "",
+        sender: json[ModelKey.prevSender] ?? "",
+        timestamp: json[ModelKey.prevTimestamp] == null
+            ? DateTime.now()
+            : DateTime.parse(json[ModelKey.prevTimestamp]),
+      );
+
+  Map<String, dynamic> toJson() => {
+        ModelKey.prevContent: content,
+        ModelKey.prevSender: sender,
+        ModelKey.prevTimestamp: timestamp.toIso8601String(),
+      };
+}
+
 class IGCRequestBody {
   String fullText;
   String userL1;
   String userL2;
   bool enableIT;
   bool enableIGC;
+  List<PreviousMessage> prevMessages;
 
   IGCRequestBody({
     required this.fullText,
@@ -107,6 +137,7 @@ class IGCRequestBody {
     required this.userL2,
     required this.enableIGC,
     required this.enableIT,
+    required this.prevMessages,
   });
 
   Map<String, dynamic> toJson() => {
@@ -115,5 +146,7 @@ class IGCRequestBody {
         ModelKey.userL2: userL2,
         "enable_it": enableIT,
         "enable_igc": enableIGC,
+        ModelKey.prevMessages:
+            jsonEncode(prevMessages.map((x) => x.toJson()).toList()),
       };
 }
diff --git a/lib/pangea/widgets/chat/message_toolbar.dart b/lib/pangea/widgets/chat/message_toolbar.dart
index 3c63c81fc..7c5682933 100644
--- a/lib/pangea/widgets/chat/message_toolbar.dart
+++ b/lib/pangea/widgets/chat/message_toolbar.dart
@@ -59,8 +59,12 @@ class ToolbarDisplayController {
   }
 
   void showToolbar(BuildContext context, {MessageMode? mode}) {
-    // Close keyboard, if open
-    FocusManager.instance.primaryFocus?.unfocus();
+    // Don't show toolbar if keyboard open
+    if (controller.inputFocus.hasFocus) {
+      FocusManager.instance.primaryFocus?.unfocus();
+      return;
+    }
+
     bool toolbarUp = true;
     if (highlighted) return;
     if (controller.selectMode) {
@@ -86,13 +90,12 @@ class ToolbarDisplayController {
       if (targetOffset.dy < 320) {
         final spaceBeneath = MediaQuery.of(context).size.height -
             (targetOffset.dy + transformTargetSize.height);
-        // If toolbar is open, opening toolbar beneath without scrolling can cause issues
-        // if (spaceBeneath >= 320) {
-        //   toolbarUp = false;
-        // }
+        if (spaceBeneath >= 320) {
+          toolbarUp = false;
+        }
 
         // See if it's possible to scroll up to make space
-        if (controller.scrollController.offset - targetOffset.dy + 320 >=
+        else if (controller.scrollController.offset - targetOffset.dy + 320 >=
                 controller.scrollController.position.minScrollExtent &&
             controller.scrollController.offset - targetOffset.dy + 320 <=
                 controller.scrollController.position.maxScrollExtent) {