UI elements

app/common/src/main/java/stirling/software/common/model/ApplicationProperties.java

@@ -626,6 +626,8 @@ public class ApplicationProperties {
                     private String primary = "gpt-5-nano";
                     private String fallback = "gpt-5-mini";
                     private String embedding = "text-embedding-3-small";
+                    private long connectTimeoutMillis = 10000;
+                    private long readTimeoutMillis = 60000;
                 }
 
                 @Data

app/proprietary/build.gradle

@@ -52,9 +52,9 @@ dependencies {
     api 'org.springframework.boot:spring-boot-starter-cache'
     api 'com.github.ben-manes.caffeine:caffeine'
     api 'io.swagger.core.v3:swagger-core-jakarta:2.2.38'
-    implementation 'org.springframework.ai:spring-ai-starter-model-openai'
+    api 'org.springframework.ai:spring-ai-starter-model-openai'
-    implementation 'org.springframework.ai:spring-ai-starter-model-ollama'
+    api 'org.springframework.ai:spring-ai-starter-model-ollama'
-    implementation 'org.springframework.ai:spring-ai-redis-store'
+    api 'org.springframework.ai:spring-ai-redis-store'
     implementation 'com.bucket4j:bucket4j_jdk17-core:8.15.0'
 
     // https://mvnrepository.com/artifact/com.bucket4j/bucket4j_jdk17

app/proprietary/src/main/java/stirling/software/proprietary/configuration/ChatbotAiClientConfiguration.java

@@ -0,0 +1,60 @@
+package stirling.software.proprietary.configuration;
+
+import java.net.http.HttpClient;
+import java.time.Duration;
+import java.util.Optional;
+
+import org.springframework.boot.autoconfigure.condition.ConditionalOnClass;
+import org.springframework.boot.autoconfigure.condition.ConditionalOnProperty;
+import org.springframework.boot.web.client.RestClientCustomizer;
+import org.springframework.context.annotation.Bean;
+import org.springframework.context.annotation.Configuration;
+import org.springframework.http.client.JdkClientHttpRequestFactory;
+
+import stirling.software.common.model.ApplicationProperties;
+import stirling.software.common.model.ApplicationProperties.Premium;
+import stirling.software.common.model.ApplicationProperties.Premium.ProFeatures;
+import stirling.software.common.model.ApplicationProperties.Premium.ProFeatures.Chatbot;
+
+@Configuration
+@ConditionalOnClass(RestClientCustomizer.class)
+@ConditionalOnProperty(value = "spring.ai.openai.enabled", havingValue = "true")
+public class ChatbotAiClientConfiguration {
+
+    @Bean
+    public RestClientCustomizer chatbotRestClientCustomizer(
+            ApplicationProperties applicationProperties) {
+        long connectTimeout = resolveConnectTimeout(applicationProperties);
+        long readTimeout = resolveReadTimeout(applicationProperties);
+        return builder -> builder.requestFactory(createRequestFactory(connectTimeout, readTimeout));
+    }
+
+    private JdkClientHttpRequestFactory createRequestFactory(
+            long connectTimeoutMillis, long readTimeoutMillis) {
+        HttpClient httpClient =
+                HttpClient.newBuilder()
+                        .connectTimeout(Duration.ofMillis(connectTimeoutMillis))
+                        .build();
+        JdkClientHttpRequestFactory factory = new JdkClientHttpRequestFactory(httpClient);
+        factory.setReadTimeout((int) readTimeoutMillis);
+        return factory;
+    }
+
+    private long resolveConnectTimeout(ApplicationProperties properties) {
+        long configured = resolveChatbot(properties).getModels().getConnectTimeoutMillis();
+        return configured > 0 ? configured : 30000L;
+    }
+
+    private long resolveReadTimeout(ApplicationProperties properties) {
+        long configured = resolveChatbot(properties).getModels().getReadTimeoutMillis();
+        return configured > 0 ? configured : 120000L;
+    }
+
+    private Chatbot resolveChatbot(ApplicationProperties properties) {
+        return Optional.ofNullable(properties)
+                .map(ApplicationProperties::getPremium)
+                .map(Premium::getProFeatures)
+                .map(ProFeatures::getChatbot)
+                .orElseGet(Chatbot::new);
+    }
+}

app/proprietary/src/main/java/stirling/software/proprietary/controller/ChatbotController.java

@@ -99,17 +99,16 @@ public class ChatbotController {
 
     private List<String> sessionWarnings(ChatbotSettings settings, ChatbotSession session) {
         List<String> warnings = new ArrayList<>();
-        if (settings.alphaWarning()) {
+
-            warnings.add("Chatbot feature is in alpha and may change.");
-        }
-        warnings.add("Image-based content is not supported yet.");
         if (session != null && session.isImageContentDetected()) {
-            warnings.add("Detected images will be ignored until image support ships.");
+            warnings.add("Images detected - Images are not currently supported.");
         }
+
         warnings.add("Only extracted text is sent for analysis.");
         if (session != null && session.isOcrRequested()) {
             warnings.add("OCR was requested – extra processing charges may apply.");
         }
+
         return warnings;
     }
 }

app/proprietary/src/main/java/stirling/software/proprietary/controller/ChatbotExceptionHandler.java

@@ -3,6 +3,7 @@ package stirling.software.proprietary.controller;
 import java.time.Instant;
 import java.util.Map;
 
+import org.eclipse.jetty.client.HttpResponseException;
 import org.springframework.boot.autoconfigure.condition.ConditionalOnBean;
 import org.springframework.http.HttpStatus;
 import org.springframework.http.ResponseEntity;
@@ -37,6 +38,14 @@ public class ChatbotExceptionHandler {
         return buildResponse(HttpStatus.BAD_REQUEST, ex.getMessage());
     }
 
+    @ExceptionHandler(HttpResponseException.class)
+    public ResponseEntity<Map<String, Object>> handleProvider(HttpResponseException ex) {
+        log.warn("Chatbot provider error", ex);
+        return buildResponse(
+                HttpStatus.BAD_GATEWAY,
+                "Chatbot provider rejected the request: " + ex.getMessage());
+    }
+
     private ResponseEntity<Map<String, Object>> buildResponse(HttpStatus status, String message) {
         Map<String, Object> payload =
                 Map.of(

app/proprietary/src/main/java/stirling/software/proprietary/service/chatbot/ChatbotConversationService.java

@@ -204,7 +204,19 @@ public class ChatbotConversationService {
             List<ChatbotTextChunk> context,
             Map<String, String> metadata) {
         Prompt requestPrompt = buildPrompt(settings, model, prompt, session, context, metadata);
-        ChatResponse response = chatModel.call(requestPrompt);
+        ChatResponse response;
+        try {
+            response = chatModel.call(requestPrompt);
+        } catch (org.eclipse.jetty.client.HttpResponseException ex) {
+            throw new ChatbotException(
+                    "Chat model rejected the request: " + sanitizeRemoteMessage(ex.getMessage()),
+                    ex);
+        } catch (RuntimeException ex) {
+            throw new ChatbotException(
+                    "Failed to contact chat model provider: "
+                            + sanitizeRemoteMessage(ex.getMessage()),
+                    ex);
+        }
         String content =
                 Optional.ofNullable(response)
                         .map(ChatResponse::getResults)
@@ -298,4 +310,11 @@ public class ChatbotConversationService {
 
     private record ModelReply(
             String answer, double confidence, boolean requiresEscalation, String rationale) {}
+
+    private String sanitizeRemoteMessage(String message) {
+        if (!StringUtils.hasText(message)) {
+            return "unexpected provider error";
+        }
+        return message.replaceAll("(?i)api[-_ ]?key\\s*=[^\\s]+", "api-key=***");
+    }
 }

app/proprietary/src/main/java/stirling/software/proprietary/service/chatbot/ChatbotIngestionService.java

@@ -138,7 +138,20 @@ public class ChatbotIngestionService {
         if (chunkTexts.isEmpty()) {
             throw new ChatbotException("Unable to split document text into retrievable chunks");
         }
-        EmbeddingResponse response = embeddingModel.embedForResponse(chunkTexts);
+        EmbeddingResponse response;
+        try {
+            response = embeddingModel.embedForResponse(chunkTexts);
+        } catch (org.eclipse.jetty.client.HttpResponseException ex) {
+            throw new ChatbotException(
+                    "Embedding provider rejected the request: "
+                            + sanitizeRemoteMessage(ex.getMessage()),
+                    ex);
+        } catch (RuntimeException ex) {
+            throw new ChatbotException(
+                    "Failed to compute embeddings for chatbot ingestion: "
+                            + sanitizeRemoteMessage(ex.getMessage()),
+                    ex);
+        }
         if (response.getResults().size() != chunkTexts.size()) {
             throw new ChatbotException("Mismatch between chunks and embedding results");
         }
@@ -165,4 +178,11 @@ public class ChatbotIngestionService {
                 chunks.size());
         return chunks;
     }
+
+    private String sanitizeRemoteMessage(String message) {
+        if (!StringUtils.hasText(message)) {
+            return "unexpected provider error";
+        }
+        return message.replaceAll("(?i)api[-_ ]?key\\s*=[^\\s]+", "api-key=***");
+    }
 }

frontend/public/locales/en-GB/translation.json

@@ -5140,5 +5140,59 @@
     "offline": "Backend Offline",
     "starting": "Backend starting up...",
     "wait": "Please wait for the backend to finish launching and try again."
+  },
+  "chatbot": {
+    "title": "Stirling PDF Bot",
+    "alphaBadge": "Alpha",
+    "alphaTitle": "Experimental feature",
+    "alphaDescription": "This Chatbot feature is in currently in alpha and is subject to change. Image-based content is not supported yet. Responses may be imperfect, so double-check important answers.",
+    "acceptAlphaLabel": "I understand this feature is experimental and image content is not supported yet.",
+    "fileLabel": "Document to query",
+    "filePlaceholder": "Select an uploaded PDF",
+    "noFiles": "Upload a PDF from File Manager to start chatting.",
+    "ocrToggle": "Run OCR before extracting text (uses more resources)",
+    "ocrHint": "Enable when your PDF is a scan or contains images.",
+    "refreshButton": "Re-sync document",
+    "startButton": "Send document to chat",
+    "sessionSummary": "Context summary",
+    "contextDetails": "{{pages}} pages · {{chars}} characters synced",
+    "conversationTitle": "Conversation",
+    "emptyState": "Ask a question about your PDF to start the conversation.",
+    "userLabel": "You",
+    "botLabel": "Stirling Bot",
+    "confidence": "Confidence: {{value}}%",
+    "modelTag": "Model: {{name}}",
+    "escalationToggle": "Allow upgrade to GPT5-Mini for complex prompts",
+    "promptPlaceholder": "Ask anything about this PDF…",
+    "promptCounter": "{{used}} / {{limit}} characters",
+    "sendButton": "Send",
+    "viewerButton": "Chat about this PDF",
+    "toolNotice": "Chatbot lives inside the main workspace. Use the button below to focus the conversation pane on the left.",
+    "toolDescription": "Ask Stirling Bot questions about any uploaded PDF. The assistant uses your extracted text, so make sure the correct document is selected inside the chat panel.",
+    "toolOpenButton": "Open chat window",
+    "toolHint": "The chat window slides in from the left. If it is already open, this button simply focuses it and passes along the currently selected PDF.",
+    "toolTitleMenu": "Chatbot (Alpha)",
+    "toolMenuDescription": "Chat with Stirling Bot about the contents of your PDF.",
+    "status": {
+      "runningOcr": "Running OCR and extracting text…",
+      "extracting": "Extracting text from PDF…",
+      "syncing": "Syncing document with Stirling Bot…"
+    },
+    "toasts": {
+      "noFileTitle": "No PDF selected",
+      "noFileBody": "Please choose a document before starting the chatbot.",
+      "ackTitle": "Accept alpha notice",
+      "ackBody": "Please acknowledge the alpha warning before starting.",
+      "failedSessionTitle": "Could not prepare document",
+      "failedSessionBody": "We were unable to sync this PDF with the chatbot. Please try again.",
+      "failedPromptTitle": "Unable to ask question",
+      "failedPromptBody": "The chatbot could not process your question. Wait a moment and try again.",
+      "noSessionTitle": "Sync your document first",
+      "noSessionBody": "Send your PDF to the chatbot before asking questions."
+    },
+    "noTextTitle": "No text detected in this PDF",
+    "noTextBody": "We could not find selectable text in this document. Would you like to run OCR to convert scanned pages into text?",
+    "noTextDismiss": "Maybe later",
+    "noTextRunOcr": "Run OCR and retry"
   }
 }

frontend/src/core/components/chatbot/ChatbotDrawer.tsx

@@ -1,12 +1,10 @@
-import { useEffect, useMemo, useRef, useState } from 'react';
+import { useEffect, useLayoutEffect, useMemo, useRef, useState, type KeyboardEvent } from 'react';
 import {
   ActionIcon,
-  Alert,
   Badge,
   Box,
   Button,
   Divider,
-  Drawer,
   Group,
   Modal,
   ScrollArea,
@@ -17,7 +15,7 @@ import {
   Textarea,
   Tooltip,
 } from '@mantine/core';
-import { useMediaQuery } from '@mantine/hooks';
+import { useMediaQuery, useViewportSize } from '@mantine/hooks';
 import { useTranslation } from 'react-i18next';
 import SmartToyRoundedIcon from '@mui/icons-material/SmartToyRounded';
 import WarningAmberRoundedIcon from '@mui/icons-material/WarningAmberRounded';
@@ -37,6 +35,7 @@ import {
 } from '@app/services/chatbotService';
 import { useToast } from '@app/components/toast';
 import type { StirlingFile } from '@app/types/fileContext';
+import { useSidebarContext } from '@app/contexts/SidebarContext';
 
 interface ChatMessage {
   id: string;
@@ -61,14 +60,15 @@ const MAX_PROMPT_CHARS = 4000;
 const ChatbotDrawer = () => {
   const { t } = useTranslation();
   const isMobile = useMediaQuery('(max-width: 768px)');
+  const { width: viewportWidth, height: viewportHeight } = useViewportSize();
   const { isOpen, closeChat, preferredFileId, setPreferredFileId } = useChatbot();
   const { selectors } = useFileState();
+  const { sidebarRefs } = useSidebarContext();
   const { show } = useToast();
   const files = selectors.getFiles();
   const [selectedFileId, setSelectedFileId] = useState<string | undefined>();
   const [alphaAccepted, setAlphaAccepted] = useState(false);
   const [runOcr, setRunOcr] = useState(false);
-  const [allowEscalation, setAllowEscalation] = useState(true);
   const [isStartingSession, setIsStartingSession] = useState(false);
   const [isSendingMessage, setIsSendingMessage] = useState(false);
   const [statusMessage, setStatusMessage] = useState<string>('');
@@ -80,6 +80,7 @@ const ChatbotDrawer = () => {
   const [noTextModalOpen, setNoTextModalOpen] = useState(false);
   const [pendingOcrRetry, setPendingOcrRetry] = useState(false);
   const scrollViewportRef = useRef<HTMLDivElement>(null);
+  const [panelAnchor, setPanelAnchor] = useState<{ right: number; top: number } | null>(null);
 
   const selectedFile = useMemo<StirlingFile | undefined>(
     () => files.find((file) => file.fileId === selectedFileId),
@@ -128,6 +129,34 @@ const ChatbotDrawer = () => {
     }
   }, [sessionInfo, selectedFileId]);
 
+  useLayoutEffect(() => {
+    if (isMobile || !isOpen) {
+      setPanelAnchor(null);
+      return;
+    }
+    const panelEl = sidebarRefs.toolPanelRef.current;
+    if (!panelEl) {
+      setPanelAnchor(null);
+      return;
+    }
+    const updateAnchor = () => {
+      const rect = panelEl.getBoundingClientRect();
+      setPanelAnchor({
+        right: rect.right,
+        top: rect.top,
+      });
+    };
+    updateAnchor();
+    const observer = typeof ResizeObserver !== 'undefined' ? new ResizeObserver(() => updateAnchor()) : null;
+    observer?.observe(panelEl);
+    const handleResize = () => updateAnchor();
+    window.addEventListener('resize', handleResize);
+    return () => {
+      observer?.disconnect();
+      window.removeEventListener('resize', handleResize);
+    };
+  }, [isMobile, isOpen, sidebarRefs.toolPanelRef]);
+
   const handleAlphaAccept = (checked: boolean) => {
     setAlphaAccepted(checked);
     if (typeof window !== 'undefined') {
@@ -264,7 +293,7 @@ const ChatbotDrawer = () => {
       const reply = await sendChatbotPrompt({
         sessionId: sessionInfo.sessionId,
         prompt: trimmedPrompt,
-        allowEscalation,
+        allowEscalation: true,
       });
       setWarnings(reply.warnings ?? []);
       const assistant = convertAssistantMessage(reply);
@@ -302,6 +331,22 @@ const ChatbotDrawer = () => {
   );
 
   const disablePromptInput = !sessionInfo || isStartingSession || isSendingMessage;
+  const canSend = !disablePromptInput && prompt.trim().length > 0;
+
+  const handlePromptKeyDown = (event: KeyboardEvent<HTMLTextAreaElement>) => {
+    if (
+      event.key === 'Enter' &&
+      !event.shiftKey &&
+      !event.metaKey &&
+      !event.ctrlKey &&
+      !event.altKey
+    ) {
+      if (canSend) {
+        event.preventDefault();
+        handleSendMessage();
+      }
+    }
+  };
 
   const drawerTitle = (
     <Group gap="xs">
@@ -313,50 +358,148 @@ const ChatbotDrawer = () => {
 
   const assistantWarnings = warnings.filter(Boolean);
 
+  const safeViewportWidth =
+      viewportWidth || (typeof window !== 'undefined' ? window.innerWidth : 1280);
+  const safeViewportHeight =
+      viewportHeight || (typeof window !== 'undefined' ? window.innerHeight : 900);
+  const desktopLeft = !isMobile ? (panelAnchor ? panelAnchor.right + 16 : 280) : undefined;
+  const desktopBottom = !isMobile ? 24 : undefined;
+  const desktopWidth = !isMobile
+      ? Math.min(440, Math.max(320, safeViewportWidth - (desktopLeft ?? 24) - 240))
+      : undefined;
+  const desktopHeightPx = !isMobile
+      ? Math.max(520, Math.min(safeViewportHeight - 48, Math.round(safeViewportHeight * 0.85)))
+      : undefined;
+
+  const renderMessageBubble = (message: ChatMessage) => {
+    const isUser = message.role === 'user';
+    const bubbleColor = isUser ? '#1f7ae0' : '#f3f4f6';
+    const textColor = isUser ? '#fff' : '#1f1f1f';
+
     return (
-    <Drawer
+      <Box
+        key={message.id + message.role + message.createdAt.getTime()}
+        style={{
+          display: 'flex',
+          justifyContent: isUser ? 'flex-end' : 'flex-start',
+        }}
+      >
+        <Box
+          p="sm"
+          maw="85%"
+          bg={bubbleColor}
+          style={{
+            borderRadius: 14,
+            borderTopRightRadius: isUser ? 4 : 14,
+            borderTopLeftRadius: isUser ? 14 : 4,
+            boxShadow: '0 2px 12px rgba(16,24,40,0.06)',
+          }}
+        >
+          <Group justify="space-between" mb={4} gap="xs">
+            <Text size="xs" c={isUser ? 'rgba(255,255,255,0.8)' : 'dimmed'} tt="uppercase">
+              {isUser ? t('chatbot.userLabel', 'You') : t('chatbot.botLabel', 'Stirling Bot')}
+            </Text>
+            {!isUser && message.confidence !== undefined && (
+              <Badge
+                size="xs"
+                variant="light"
+                color={message.confidence >= 0.6 ? 'green' : 'yellow'}
+              >
+                {t('chatbot.confidence', 'Confidence: {{value}}%', {
+                  value: Math.round(message.confidence * 100),
+                })}
+              </Badge>
+            )}
+          </Group>
+          <Text size="sm" c={textColor} style={{ whiteSpace: 'pre-wrap' }}>
+            {message.content}
+          </Text>
+          {!isUser && message.modelUsed && (
+            <Text size="xs" c="dimmed" mt={4}>
+              {t('chatbot.modelTag', 'Model: {{name}}', { name: message.modelUsed })}
+            </Text>
+          )}
+        </Box>
+      </Box>
+    );
+  };
+
+  return (
+    <>
+      <Modal
         opened={isOpen}
         onClose={closeChat}
-      position="left"
+        withCloseButton
-      overlayProps={{ opacity: 0.65, blur: 3 }}
+        radius="lg"
-      size={isMobile ? '100%' : 420}
+        overlayProps={{ opacity: 0.5, blur: 2 }}
+        fullScreen={isMobile}
+        centered={isMobile}
         title={drawerTitle}
-      withinPortal
+        styles={{
-      closeOnClickOutside={false}
+          content: {
+            width: isMobile ? '100%' : desktopWidth,
+            left: isMobile ? undefined : desktopLeft,
+            right: isMobile ? 0 : undefined,
+            margin: isMobile ? undefined : 0,
+            top: isMobile ? undefined : undefined,
+            bottom: isMobile ? 0 : desktopBottom,
+            position: isMobile ? undefined : 'fixed',
+            height: isMobile ? '100%' : desktopHeightPx ? `${desktopHeightPx}px` : '75vh',
+            overflow: 'hidden',
+          },
+          body: {
+            paddingTop: 'var(--mantine-spacing-md)',
+            paddingBottom: 'var(--mantine-spacing-md)',
+            height: '100%',
+            display: 'flex',
+            flexDirection: 'column',
+          },
+        }}
+        transitionProps={{ transition: 'slide-left', duration: 200 }}
       >
-      <Stack gap="md" h="100%">
+        <Stack gap="sm" h="100%" style={{ minHeight: 0 }}>
-        <Alert color="yellow" icon={<WarningAmberRoundedIcon fontSize="small" />}
+        <Box
-          title={t('chatbot.alphaTitle', 'Experimental feature')}
+          p="sm"
+          style={{
+            border: '1px solid var(--border-subtle)',
+            borderRadius: 8,
+            backgroundColor: 'var(--bg-subtle)',
+            display: 'flex',
+            gap: '0.5rem',
+            alignItems: 'flex-start',
+          }}
         >
+          <WarningAmberRoundedIcon fontSize="small" style={{ color: 'var(--text-warning)' }} />
+          <Box>
+            <Text fw={600}>{t('chatbot.alphaTitle', 'Experimental feature')}</Text>
+            <Text size="sm">
               {t('chatbot.alphaDescription', 'This chatbot is in alpha. It currently ignores images and may produce inaccurate answers. Your PDF text stays local until you confirm you want to chat.')}
-        </Alert>
+            </Text>
-
+          </Box>
-        <Switch
+        </Box>
-          checked={alphaAccepted}
-          label={t('chatbot.acceptAlphaLabel', 'I understand this feature is experimental and image content is not supported yet.')}
-          onChange={(event) => handleAlphaAccept(event.currentTarget.checked)}
-        />
 
+        <Group align="flex-end" justify="space-between" gap="md" wrap="wrap">
           <Select
-          label={t('chatbot.fileLabel', 'Document to query')}
+            label={t('chatbot.fileLabel', 'Document')}
             placeholder={t('chatbot.filePlaceholder', 'Select an uploaded PDF')}
             data={fileOptions}
             value={selectedFileId}
             onChange={(value) => setSelectedFileId(value || undefined)}
             nothingFoundMessage={t('chatbot.noFiles', 'Upload a PDF from File Manager to start chatting.')}
+            style={{ flex: '1 1 200px' }}
+          />
+          <Stack gap={4} style={{ minWidth: 160 }}>
+            <Switch
+              checked={alphaAccepted}
+              label={t('chatbot.acceptAlphaLabel', 'Alpha notice acknowledged')}
+              onChange={(event) => handleAlphaAccept(event.currentTarget.checked)}
             />
-
-        <Group justify="space-between" align="center">
             <Switch
               checked={runOcr}
               onChange={(event) => setRunOcr(event.currentTarget.checked)}
-            label={t('chatbot.ocrToggle', 'Run OCR before extracting text (uses more resources)')}
+              label={t('chatbot.ocrToggle', 'Run OCR before extracting text')}
             />
-          <Tooltip label={t('chatbot.ocrHint', 'Enable when your PDF is a scan or contains images.')}>
+          </Stack>
-            <ActionIcon variant="subtle" aria-label={t('chatbot.ocrHint', 'OCR hint')}>
-              <SmartToyRoundedIcon fontSize="small" />
-            </ActionIcon>
-          </Tooltip>
         </Group>
 
         <Button
@@ -373,7 +516,16 @@ const ChatbotDrawer = () => {
         </Button>
 
         {statusMessage && (
-          <Alert color="blue">{statusMessage}</Alert>
+          <Box
+            p="sm"
+            style={{
+              border: '1px solid var(--border-subtle)',
+              borderRadius: 8,
+              backgroundColor: 'var(--bg-muted)',
+            }}
+          >
+            <Text size="sm" c="blue">{statusMessage}</Text>
+          </Box>
         )}
 
         {sessionInfo && contextStats && (
@@ -388,70 +540,55 @@ const ChatbotDrawer = () => {
           </Box>
         )}
 
-        {assistantWarnings.length > 0 && (
-          <Alert color="yellow">
-            <Stack gap={4}>
-              {assistantWarnings.map((warning) => (
-                <Text key={warning} size="sm">{warning}</Text>
-              ))}
-            </Stack>
-          </Alert>
-        )}
-
         <Divider label={t('chatbot.conversationTitle', 'Conversation')} />
 
-        <ScrollArea viewportRef={scrollViewportRef} style={{ flex: 1 }}>
+        <Box style={{ flex: 1, minHeight: 0 }}>
-          <Stack gap="sm" pr="sm">
+          <ScrollArea viewportRef={scrollViewportRef} style={{ height: '100%' }}>
+            <Stack gap="sm" pr="xs">
+              {assistantWarnings.length > 0 &&
+                assistantWarnings.map((warning) => (
+                  <Box
+                    key={warning}
+                    p="sm"
+                    bg="var(--bg-muted)"
+                    style={{ borderRadius: 12, border: '1px dashed var(--border-subtle)' }}
+                  >
+                    <Group gap="xs" align="flex-start">
+                      <WarningAmberRoundedIcon fontSize="small" style={{ color: 'var(--text-warning)' }} />
+                      <Text size="sm">{warning}</Text>
+                    </Group>
+                  </Box>
+                ))}
               {messages.length === 0 && (
                 <Text size="sm" c="dimmed">
                   {t('chatbot.emptyState', 'Ask a question about your PDF to start the conversation.')}
                 </Text>
               )}
-            {messages.map((message) => (
+              {messages.map(renderMessageBubble)}
-              <Box
-                key={message.id + message.role + message.createdAt.getTime()}
-                p="sm"
-                bg={message.role === 'user' ? 'var(--bg-toolbar)' : 'var(--bg-panel)'}
-                style={{ borderRadius: 8 }}
-              >
-                <Group justify="space-between" mb={4} wrap="nowrap">
-                  <Text size="xs" c="dimmed" tt="uppercase">
-                    {message.role === 'user'
-                      ? t('chatbot.userLabel', 'You')
-                      : t('chatbot.botLabel', 'Stirling Bot')}
-                  </Text>
-                  {message.role === 'assistant' && message.confidence !== undefined && (
-                    <Badge size="xs" variant="light" color={message.confidence >= 0.6 ? 'green' : 'yellow'}>
-                      {t('chatbot.confidence', 'Confidence: {{value}}%', {
-                        value: Math.round(message.confidence * 100),
-                      })}
-                    </Badge>
-                  )}
-                </Group>
-                <Text size="sm" style={{ whiteSpace: 'pre-wrap' }}>{message.content}</Text>
-                {message.role === 'assistant' && message.modelUsed && (
-                  <Text size="xs" c="dimmed" mt={4}>
-                    {t('chatbot.modelTag', 'Model: {{name}}', { name: message.modelUsed })}
-                  </Text>
-                )}
-              </Box>
-            ))}
             </Stack>
           </ScrollArea>
+        </Box>
 
-        <Stack gap="xs">
+        <Stack
-          <Switch
+          gap="xs"
-            checked={allowEscalation}
+          style={{
-            onChange={(event) => setAllowEscalation(event.currentTarget.checked)}
+            flexShrink: 0,
-            label={t('chatbot.escalationToggle', 'Allow upgrade to GPT5-Mini for complex prompts')}
+            border: '1px solid var(--border-subtle)',
-          />
+            borderRadius: 12,
+            padding: '0.75rem',
+            background: 'var(--bg-toolbar)',
+          }}
+        >
           <Textarea
             placeholder={t('chatbot.promptPlaceholder', 'Ask anything about this PDF…')}
-            minRows={3}
+            minRows={2}
+            autosize
+            maxRows={6}
             value={prompt}
             maxLength={MAX_PROMPT_CHARS}
             onChange={(event) => setPrompt(event.currentTarget.value)}
             disabled={disablePromptInput}
+            onKeyDown={handlePromptKeyDown}
           />
           <Group justify="space-between">
             <Text size="xs" c="dimmed">
@@ -464,13 +601,14 @@ const ChatbotDrawer = () => {
               rightSection={<SendRoundedIcon fontSize="small" />}
               onClick={handleSendMessage}
               loading={isSendingMessage}
-              disabled={disablePromptInput || prompt.trim().length === 0}
+              disabled={!canSend}
             >
               {t('chatbot.sendButton', 'Send')}
             </Button>
           </Group>
         </Stack>
       </Stack>
+      </Modal>
 
       <Modal
         opened={noTextModalOpen}
@@ -501,7 +639,7 @@ const ChatbotDrawer = () => {
           </Group>
         </Stack>
       </Modal>
-    </Drawer>
+    </>
   );
 };
 

frontend/src/core/components/shared/RightRail.tsx

@@ -16,6 +16,7 @@ import LocalIcon from '@app/components/shared/LocalIcon';
 import { RightRailFooterExtensions } from '@app/components/rightRail/RightRailFooterExtensions';
 
 import { useSidebarContext } from '@app/contexts/SidebarContext';
+import { useChatbot } from '@app/contexts/ChatbotContext';
 import { RightRailButtonConfig, RightRailRenderContext, RightRailSection } from '@app/types/rightRail';
 
 const SECTION_ORDER: RightRailSection[] = ['top', 'middle', 'bottom'];
@@ -41,6 +42,7 @@ export default function RightRail() {
   const viewerContext = React.useContext(ViewerContext);
   const { toggleTheme } = useRainbowThemeContext();
   const { buttons, actions, allButtonsDisabled } = useRightRail();
+  const { openChat } = useChatbot();
 
   const { pageEditorFunctions, toolPanelMode, leftPanelView } = useToolWorkflow();
   const disableForFullscreen = toolPanelMode === 'fullscreen' && leftPanelView === 'toolPicker';
@@ -55,6 +57,8 @@ export default function RightRail() {
   const pageEditorTotalPages = pageEditorFunctions?.totalPages ?? 0;
   const pageEditorSelectedCount = pageEditorFunctions?.selectedPageIds?.length ?? 0;
   const exportState = viewerContext?.getExportState?.();
+  const chatLabel = t('chatbot.viewerButton', 'Chat about this PDF');
+  const viewerActiveFile = activeFiles[viewerContext?.activeFileIndex ?? 0];
 
   const totalItems = useMemo(() => {
     if (currentView === 'pageEditor') return pageEditorTotalPages;
@@ -222,6 +226,24 @@ export default function RightRail() {
             </ActionIcon>,
             downloadTooltip
           )}
+          {renderWithTooltip(
+            <ActionIcon
+              variant="subtle"
+              radius="md"
+              className="right-rail-icon"
+              onClick={() => {
+                if (viewerActiveFile) {
+                  openChat({ source: 'viewer', fileId: viewerActiveFile.fileId });
+                } else {
+                  openChat({ source: 'viewer' });
+                }
+              }}
+              disabled={!viewerActiveFile}
+            >
+              <LocalIcon icon="smart-toy-rounded" width="1.5rem" height="1.5rem" />
+            </ActionIcon>,
+            chatLabel
+          )}
         </div>
 
         <div className="right-rail-spacer" />

frontend/src/core/components/viewer/useViewerRightRailButtons.tsx

@@ -7,17 +7,14 @@ import LocalIcon from '@app/components/shared/LocalIcon';
 import { Tooltip } from '@app/components/shared/Tooltip';
 import { SearchInterface } from '@app/components/viewer/SearchInterface';
 import ViewerAnnotationControls from '@app/components/shared/rightRail/ViewerAnnotationControls';
-import { useChatbot } from '@app/contexts/ChatbotContext';
 import { useFileState } from '@app/contexts/FileContext';
 
 export function useViewerRightRailButtons() {
   const { t } = useTranslation();
   const viewer = useViewer();
-  const { openChat } = useChatbot();
   const { selectors } = useFileState();
   const filesSignature = selectors.getFilesSignature();
   const files = useMemo(() => selectors.getFiles(), [selectors, filesSignature]);
-  const activeFile = files[viewer.activeFileIndex] || files[0];
   const [isPanning, setIsPanning] = useState<boolean>(() => viewer.getPanState()?.isPanning ?? false);
 
   // Lift i18n labels out of memo for clarity
@@ -26,7 +23,6 @@ export function useViewerRightRailButtons() {
   const rotateLeftLabel = t('rightRail.rotateLeft', 'Rotate Left');
   const rotateRightLabel = t('rightRail.rotateRight', 'Rotate Right');
   const sidebarLabel = t('rightRail.toggleSidebar', 'Toggle Sidebar');
-  const chatLabel = t('chatbot.viewerButton', 'Chat about this PDF');
 
   const viewerButtons = useMemo<RightRailButtonWithAction[]>(() => {
     return [
@@ -61,20 +57,6 @@ export function useViewerRightRailButtons() {
           </Tooltip>
         )
       },
-      {
-        id: 'viewer-chatbot',
-        icon: <LocalIcon icon="smart-toy-rounded" width="1.5rem" height="1.5rem" />,
-        tooltip: chatLabel,
-        ariaLabel: chatLabel,
-        section: 'top' as const,
-        order: 15,
-        disabled: !activeFile,
-        onClick: () => {
-          if (activeFile) {
-            openChat({ source: 'viewer', fileId: activeFile.fileId });
-          }
-        },
-      },
       {
         id: 'viewer-pan-mode',
         tooltip: panLabel,
@@ -150,9 +132,6 @@ export function useViewerRightRailButtons() {
     rotateLeftLabel,
     rotateRightLabel,
     sidebarLabel,
-    chatLabel,
-    openChat,
-    activeFile?.fileId,
   ]);
 
   useRightRailButtons(viewerButtons);