diff --git a/web/chat/typeahead-tooltip.react.js b/web/chat/typeahead-tooltip.react.js
--- a/web/chat/typeahead-tooltip.react.js
+++ b/web/chat/typeahead-tooltip.react.js
@@ -8,6 +8,7 @@
 
 import type { InputState } from '../input/input-state';
 import {
+  getTypeaheadOverlayScroll,
   getTypeaheadTooltipActions,
   getTypeaheadTooltipButtons,
   getTypeaheadTooltipPosition,
@@ -36,6 +37,8 @@
     setChosenPositionInOverlay,
   ] = React.useState<number>(0);
 
+  const overlayRef = React.useRef<?HTMLDivElement>();
+
   React.useEffect(() => {
     setChosenPositionInOverlay(0);
   }, [suggestedUsers]);
@@ -143,6 +146,16 @@
     inputState.setTypeaheadState,
   ]);
 
+  React.useEffect(() => {
+    const current = overlayRef.current;
+    if (current) {
+      current.scrollTop = getTypeaheadOverlayScroll(
+        current.scrollTop,
+        chosenPositionInOverlay,
+      );
+    }
+  }, [chosenPositionInOverlay]);
+
   if (suggestedUsers.length === 0) {
     return null;
   }
@@ -153,7 +166,11 @@
   });
 
   return (
-    <div className={overlayClasses} style={tooltipPositionStyle}>
+    <div
+      ref={overlayRef}
+      className={overlayClasses}
+      style={tooltipPositionStyle}
+    >
       {tooltipButtons}
     </div>
   );
diff --git a/web/utils/typeahead-utils.js b/web/utils/typeahead-utils.js
--- a/web/utils/typeahead-utils.js
+++ b/web/utils/typeahead-utils.js
@@ -153,6 +153,30 @@
   });
 }
 
+function getTypeaheadOverlayScroll(
+  currentScrollTop: number,
+  chosenActionPosition: number,
+): number {
+  const upperButtonBoundary = chosenActionPosition * typeaheadStyle.rowHeight;
+  const lowerButtonBoundary =
+    (chosenActionPosition + 1) * typeaheadStyle.rowHeight;
+
+  if (upperButtonBoundary < currentScrollTop) {
+    return upperButtonBoundary;
+  } else if (
+    lowerButtonBoundary - typeaheadStyle.tooltipMaxHeight >
+    currentScrollTop
+  ) {
+    return (
+      lowerButtonBoundary +
+      typeaheadStyle.tooltipVerticalPadding -
+      typeaheadStyle.tooltipMaxHeight
+    );
+  }
+
+  return currentScrollTop;
+}
+
 function getTypeaheadTooltipPosition(
   textarea: HTMLTextAreaElement,
   actionsLength: number,
@@ -188,5 +212,6 @@
   getCaretOffsets,
   getTypeaheadTooltipActions,
   getTypeaheadTooltipButtons,
+  getTypeaheadOverlayScroll,
   getTypeaheadTooltipPosition,
 };