diff --git a/com.microsoft.copilot.eclipse.ui/src/com/microsoft/copilot/eclipse/ui/chat/BaseTurnWidget.java b/com.microsoft.copilot.eclipse.ui/src/com/microsoft/copilot/eclipse/ui/chat/BaseTurnWidget.java
index 1218ce5a..9f099223 100644
--- a/com.microsoft.copilot.eclipse.ui/src/com/microsoft/copilot/eclipse/ui/chat/BaseTurnWidget.java
+++ b/com.microsoft.copilot.eclipse.ui/src/com/microsoft/copilot/eclipse/ui/chat/BaseTurnWidget.java
@@ -23,6 +23,7 @@
 import org.eclipse.ui.PlatformUI;
 import org.osgi.service.event.EventHandler;
 
+import com.microsoft.copilot.eclipse.core.Constants;
 import com.microsoft.copilot.eclipse.core.CopilotCore;
 import com.microsoft.copilot.eclipse.core.chat.ConfirmationContent;
 import com.microsoft.copilot.eclipse.core.events.CopilotEventConstants;
@@ -36,6 +37,7 @@
 import com.microsoft.copilot.eclipse.core.persistence.CopilotTurnData.EditAgentRoundData;
 import com.microsoft.copilot.eclipse.core.persistence.CopilotTurnData.ReplyData;
 import com.microsoft.copilot.eclipse.core.persistence.CopilotTurnData.ToolCallData;
+import com.microsoft.copilot.eclipse.ui.CopilotUi;
 import com.microsoft.copilot.eclipse.ui.chat.services.AvatarService;
 import com.microsoft.copilot.eclipse.ui.chat.services.ChatServiceManager;
 import com.microsoft.copilot.eclipse.ui.utils.SwtUtils;
@@ -604,16 +606,16 @@ protected void ensureFooterAtBottom() {
    * @param code the server error code
    * @param modelProviderName the BYOK model-provider name, or {@code null} for built-in models
    */
-  protected void createWarnDialog(String message, int code, String modelProviderName) {
+  protected Composite createWarnDialog(String message, int code, String modelProviderName) {
     // TODO: Remove this legacy fallback after TBB is officially released.
     // When the language server has not enabled token-based billing yet, restore the original
     // main-branch warning behavior (no plan-driven actions; single upgrade button on the legacy
     // 30-day free trial message).
     if (!this.serviceManager.getAuthStatusManager().getQuotaStatus().tokenBasedBillingEnabled()) {
-      new WarnWidget(this, SWT.BOTTOM, message, code);
+      WarnWidget warnWidget = new WarnWidget(this, SWT.BOTTOM, message, code);
       ensureFooterAtBottom();
       requestLayout();
-      return;
+      return warnWidget;
     }
     boolean byokQuotaExceeded = QuotaActions.isByokQuotaExceeded(code, modelProviderName);
     String displayMessage = byokQuotaExceeded ? Messages.chat_warnWidget_byokQuotaUsageMessage : message;
@@ -627,9 +629,11 @@ protected void createWarnDialog(String message, int code, String modelProviderNa
           && quotaStatus.premiumInteractions().overagePermitted();
       canUpgradePlan = quotaStatus.canUpgradePlan();
     }
-    new WarnWidget(this, SWT.NONE, displayMessage, planForActions, overageEnabled, canUpgradePlan);
+    WarnWidget warnWidget =
+        new WarnWidget(this, SWT.NONE, displayMessage, planForActions, overageEnabled, canUpgradePlan);
     ensureFooterAtBottom();
     requestLayout();
+    return warnWidget;
   }
 
   /**
@@ -666,6 +670,19 @@ public CompletableFuture<LanguageModelToolConfirmationResult> requestToolExecuti
 
     this.getParent().requestLayout();
 
+    // Ensure the chat content viewer scrolls to show the newly created confirmation
+    // dialog. Walk up the composite hierarchy to find a ChatContentViewer
+    // and request scrolling. Use async exec because layout needs to complete first.
+    SwtUtils.invokeOnDisplayThreadAsync(() -> {
+      ChatContentViewer viewer = SwtUtils.findParentOfType(this.getParent(), ChatContentViewer.class);
+      if (viewer != null) {
+        if (this.confirmDialog != null && !this.confirmDialog.isDisposed()) {
+          viewer.showControl(this.confirmDialog);
+        }
+      }
+
+    }, this.getParent());
+
     return toolConfirmationFuture;
   }
 
diff --git a/com.microsoft.copilot.eclipse.ui/src/com/microsoft/copilot/eclipse/ui/chat/ChatContentViewer.java b/com.microsoft.copilot.eclipse.ui/src/com/microsoft/copilot/eclipse/ui/chat/ChatContentViewer.java
index 83e197e7..b3db64b4 100644
--- a/com.microsoft.copilot.eclipse.ui/src/com/microsoft/copilot/eclipse/ui/chat/ChatContentViewer.java
+++ b/com.microsoft.copilot.eclipse.ui/src/com/microsoft/copilot/eclipse/ui/chat/ChatContentViewer.java
@@ -468,9 +468,17 @@ public BaseTurnWidget getTurnWidget(String turnId) {
   }
 
   private void renderWarnMessageWithUpgradePlanButton(String errorMessage, int code, String modelProviderName) {
-    latestTurnWidget.createWarnDialog(errorMessage, code, modelProviderName);
+    Composite warnWidget = latestTurnWidget.createWarnDialog(errorMessage, code, modelProviderName);
     refreshLayoutFull();
     scrollToLatestUserTurn();
+    // Ensure the chat content viewer scrolls to show the newly created warning banner. Walk up the composite hierarchy
+    // to find a ChatContentViewer and request scrolling. Use async exec because layout needs to complete first.
+    SwtUtils.invokeOnDisplayThreadAsync(() -> {
+      if (warnWidget != null && !warnWidget.isDisposed()) {
+        showControl(warnWidget);
+      }
+
+    }, this.getParent());
   }
 
   /**
@@ -483,6 +491,12 @@ public void renderErrorMessage(String errorMessage) {
     this.errorWidget = new ErrorWidget(cmpContent, SWT.BOTTOM, errorMessage);
     refreshLayoutFull();
     scrollToLatestUserTurn();
+    // Ensure the chat content viewer scrolls to show the newly created error banner.
+    SwtUtils.invokeOnDisplayThreadAsync(() -> {
+      if (this.errorWidget != null && !this.errorWidget.isDisposed()) {
+        this.showControl(this.errorWidget);
+      }
+    }, this.getParent());
   }
 
   /**
@@ -770,6 +784,50 @@ private int topOf(Control target) {
     return running;
   }
 
+  /**
+   * Scrolls the viewport to make {@code target} visible, equivalent to
+   * {@link org.eclipse.swt.custom.ScrolledComposite#showControl(Control)}.
+   *
+   * <p>Walks up the widget tree to find the direct child of {@code cmpContent} that contains
+   * {@code target}, computes the content-coordinate position of {@code target} by summing
+   * the turn's {@link #topOf} value with the local y offsets down to {@code target}, then
+   * adjusts {@link #scrollOffset} by the minimum amount needed to bring {@code target} fully
+   * into the viewport.</p>
+   */
+  public void showControl(Composite target) {
+    if (target == null || target.isDisposed()) {
+      return;
+    }
+    // Walk up to find the direct child of cmpContent that is the ancestor of target.
+    Control ancestor = target;
+    while (ancestor != null && ancestor.getParent() != cmpContent) {
+      ancestor = ancestor.getParent();
+    }
+    if (ancestor == null || ancestor.getParent() != cmpContent) {
+      return;
+    }
+    // Content-coordinate top of the enclosing turn widget.
+    int ancestorTop = topOf(ancestor);
+    // Accumulate the local y offset by walking from target up to (but not including) ancestor.
+    int localY = 0;
+    for (Control c = target; c != ancestor; c = c.getParent()) {
+      localY += c.getLocation().y;
+    }
+    int targetTop = ancestorTop + localY;
+    int targetBottom = targetTop + target.getSize().y;
+    int viewport = getClientArea().height;
+    // Scroll the minimum amount: down if target is below the visible area, up if above.
+    int newOffset = scrollOffset;
+    if (targetBottom > scrollOffset + viewport) {
+      newOffset = targetBottom - viewport;
+    }
+    if (targetTop < newOffset) {
+      newOffset = targetTop;
+    }
+    scrollOffset = clampOffset(newOffset);
+    relayoutWindow();
+  }
+
   @Override
   public void dispose() {
     pendingEvents.clear();
diff --git a/com.microsoft.copilot.eclipse.ui/src/com/microsoft/copilot/eclipse/ui/utils/SwtUtils.java b/com.microsoft.copilot.eclipse.ui/src/com/microsoft/copilot/eclipse/ui/utils/SwtUtils.java
index 0a054490..73180b8c 100644
--- a/com.microsoft.copilot.eclipse.ui/src/com/microsoft/copilot/eclipse/ui/utils/SwtUtils.java
+++ b/com.microsoft.copilot.eclipse.ui/src/com/microsoft/copilot/eclipse/ui/utils/SwtUtils.java
@@ -48,8 +48,30 @@ private SwtUtils() {
   }
 
   private static final String INLINE_ANNOTATION_COLOR_KEY = "org.eclipse.ui.editors.inlineAnnotationColor";
+
   private static final int DEFAULT_GHOST_TEXT_SCALE = 128;
 
+  /**
+   * Walks up the parent chain of the given control and returns the first ancestor that is an instance of the specified
+   * type, or {@code null} if none is found.
+   *
+   * @param <T> the target type
+   * @param control the starting control (may be {@code null})
+   * @param type the class to search for
+   * @return the first matching ancestor, or {@code null}
+   */
+  @Nullable
+  public static <T> T findParentOfType(Control control, Class<T> type) {
+    Control current = control;
+    while (current != null) {
+      if (type.isInstance(current)) {
+        return type.cast(current);
+      }
+      current = current.getParent();
+    }
+    return null;
+  }
+
   /**
    * Invokes the given runnable on the display thread.
    */