diff --git a/packages/twenty-front/src/modules/ai/components/AiChatQuestionCard.tsx b/packages/twenty-front/src/modules/ai/components/AiChatQuestionCard.tsx
index e36ec0eb1b..b181c10f36 100644
--- a/packages/twenty-front/src/modules/ai/components/AiChatQuestionCard.tsx
+++ b/packages/twenty-front/src/modules/ai/components/AiChatQuestionCard.tsx
@@ -330,6 +330,13 @@ export const AiChatQuestionCard = ({
   const handleKeyDown = (event: KeyboardEvent<HTMLTextAreaElement>) => {
     if (event.key === 'Enter' && !event.shiftKey) {
       event.preventDefault();
+
+      if (!isLastQuestion) {
+        setCurrentIndex(currentIndex + 1);
+
+        return;
+      }
+
       handleSend();
     }
   };
diff --git a/packages/twenty-front/src/modules/ai/components/AiChatQuestionStatusRenderer.tsx b/packages/twenty-front/src/modules/ai/components/AiChatQuestionStatusRenderer.tsx
index 6f8e855d69..27fd4b383e 100644
--- a/packages/twenty-front/src/modules/ai/components/AiChatQuestionStatusRenderer.tsx
+++ b/packages/twenty-front/src/modules/ai/components/AiChatQuestionStatusRenderer.tsx
@@ -22,26 +22,40 @@ const StyledContainer = styled.div`
   }
 `;
 
-const StyledContent = styled.div`
-  display: flex;
-  flex-direction: column;
-  gap: ${themeCssVariables.spacing['0.5']};
-  min-width: 0;
-`;
-
 const StyledMessage = styled.span`
   color: ${themeCssVariables.font.color.tertiary};
   font-size: ${themeCssVariables.font.size.md};
   font-weight: ${themeCssVariables.font.weight.medium};
 `;
 
-const StyledAnswerLine = styled.span`
+const StyledAnswersCard = styled.div`
+  background-color: ${themeCssVariables.background.transparent.lighter};
+  border: 1px solid ${themeCssVariables.border.color.medium};
+  border-radius: ${themeCssVariables.border.radius.sm};
+  box-sizing: border-box;
+  display: flex;
+  flex-direction: column;
+  gap: ${themeCssVariables.spacing[2]};
+  padding: ${themeCssVariables.spacing[3]};
+`;
+
+const StyledAnswerBlock = styled.div`
+  display: flex;
+  flex-direction: column;
+  gap: ${themeCssVariables.spacing['0.5']};
+  min-width: 0;
+`;
+
+const StyledAnswerQuestion = styled.span`
   color: ${themeCssVariables.font.color.tertiary};
   font-size: ${themeCssVariables.font.size.sm};
+  overflow-wrap: anywhere;
 `;
 
 const StyledAnswerValue = styled.span`
   color: ${themeCssVariables.font.color.secondary};
+  font-size: ${themeCssVariables.font.size.sm};
+  overflow-wrap: anywhere;
 `;
 
 export const AiChatQuestionStatusRenderer = ({
@@ -79,34 +93,32 @@ export const AiChatQuestionStatusRenderer = ({
   const answers = result?.answers ?? [];
 
   return (
-    <StyledContainer>
-      <IconHelpCircle size={theme.icon.size.sm} />
-      <StyledContent>
-        <StyledMessage>{t`Questions answered`}</StyledMessage>
-        {questions.map((question, index) => {
-          const answer = answers.find(
-            (candidate) => candidate.questionIndex === index,
-          );
-          const selectedLabels = (answer?.selectedOptionIndices ?? [])
-            .map((optionIndex) => question.options[optionIndex]?.label)
-            .filter(isNonEmptyString);
-          const freeTextAnswer = answer?.freeText ?? '';
-          const value =
-            freeTextAnswer.length > 0
-              ? freeTextAnswer
-              : selectedLabels.join(', ');
+    <StyledAnswersCard>
+      <StyledMessage>{t`Answers`}</StyledMessage>
+      {questions.map((question, index) => {
+        const answer = answers.find(
+          (candidate) => candidate.questionIndex === index,
+        );
+        const selectedLabels = (answer?.selectedOptionIndices ?? [])
+          .map((optionIndex) => question.options[optionIndex]?.label)
+          .filter(isNonEmptyString);
+        const freeTextAnswer = answer?.freeText ?? '';
+        const value =
+          freeTextAnswer.length > 0
+            ? freeTextAnswer
+            : selectedLabels.join(', ');
 
-          if (value.length === 0) {
-            return null;
-          }
+        if (value.length === 0) {
+          return null;
+        }
 
-          return (
-            <StyledAnswerLine key={index}>
-              {question.header}: <StyledAnswerValue>{value}</StyledAnswerValue>
-            </StyledAnswerLine>
-          );
-        })}
-      </StyledContent>
-    </StyledContainer>
+        return (
+          <StyledAnswerBlock key={index}>
+            <StyledAnswerQuestion>{question.question}</StyledAnswerQuestion>
+            <StyledAnswerValue>{value}</StyledAnswerValue>
+          </StyledAnswerBlock>
+        );
+      })}
+    </StyledAnswersCard>
   );
 };
diff --git a/packages/twenty-front/src/modules/ai/utils/groupContiguousThinkingStepParts.ts b/packages/twenty-front/src/modules/ai/utils/groupContiguousThinkingStepParts.ts
index 663d4c2cbb..f63d92f73b 100644
--- a/packages/twenty-front/src/modules/ai/utils/groupContiguousThinkingStepParts.ts
+++ b/packages/twenty-front/src/modules/ai/utils/groupContiguousThinkingStepParts.ts
@@ -1,6 +1,7 @@
 import { type ExtendedUIMessagePart } from 'twenty-shared/ai';
 
 import { type AssistantMessageRenderItem } from '@/ai/utils/assistantMessageRenderItem';
+import { isAskQuestionsToolPart } from '@/ai/utils/isAskQuestionsToolPart';
 import { isThinkingStepPart } from '@/ai/utils/isThinkingStepPart';
 import { type ThinkingStepPart } from '@/ai/utils/thinkingStepPart';
 
@@ -25,7 +26,7 @@ export const groupContiguousThinkingStepParts = (
       continue;
     }
 
-    if (isThinkingStepPart(part)) {
+    if (isThinkingStepPart(part) && !isAskQuestionsToolPart(part)) {
       currentThinkingParts.push(part);
       continue;
     }
diff --git a/packages/twenty-front/src/modules/ai/utils/isAskQuestionsToolPart.ts b/packages/twenty-front/src/modules/ai/utils/isAskQuestionsToolPart.ts
new file mode 100644
index 0000000000..69fe625e49
--- /dev/null
+++ b/packages/twenty-front/src/modules/ai/utils/isAskQuestionsToolPart.ts
@@ -0,0 +1,8 @@
+import { getToolName, isToolUIPart } from 'ai';
+import {
+  ASK_QUESTIONS_TOOL_NAME,
+  type ExtendedUIMessagePart,
+} from 'twenty-shared/ai';
+
+export const isAskQuestionsToolPart = (part: ExtendedUIMessagePart): boolean =>
+  isToolUIPart(part) && getToolName(part) === ASK_QUESTIONS_TOOL_NAME;