diff --git a/app/assets/javascripts/components/NotesContextMenu.tsx b/app/assets/javascripts/components/NotesContextMenu.tsx
index 17aa46cb4..b215f0463 100644
--- a/app/assets/javascripts/components/NotesContextMenu.tsx
+++ b/app/assets/javascripts/components/NotesContextMenu.tsx
@@ -31,13 +31,13 @@ const NotesContextMenu = observer(({ appState }: Props) => {
   return appState.notes.contextMenuOpen ? (
     <div
       ref={contextMenuRef}
-      className="sn-dropdown max-w-80 flex flex-col py-2 absolute"
-      style={{ ...appState.notes.contextMenuPosition }}
+      className="sn-dropdown max-h-120 max-w-80 flex flex-col py-2 overflow-y-scroll fixed"
+      style={{
+        ...appState.notes.contextMenuPosition,
+        maxHeight: appState.notes.contextMenuMaxHeight,
+      }}
     >
-      <NotesOptions
-        appState={appState}
-        closeOnBlur={closeOnBlur}
-      />
+      <NotesOptions appState={appState} closeOnBlur={closeOnBlur} />
     </div>
   ) : null;
 });
diff --git a/app/assets/javascripts/components/NotesOptions.tsx b/app/assets/javascripts/components/NotesOptions.tsx
index b6a05f96f..8c80f5f54 100644
--- a/app/assets/javascripts/components/NotesOptions.tsx
+++ b/app/assets/javascripts/components/NotesOptions.tsx
@@ -19,11 +19,16 @@ type Props = {
 export const NotesOptions = observer(
   ({ appState, closeOnBlur, onSubmenuChange }: Props) => {
     const [tagsMenuOpen, setTagsMenuOpen] = useState(false);
-    const [tagsMenuPosition, setTagsMenuPosition] = useState({
+    const [tagsMenuPosition, setTagsMenuPosition] = useState<{
+      top: number;
+      right?: number;
+      left?: number;
+    }>({
       top: 0,
       right: 0,
     });
-    const [tagsMenuMaxHeight, setTagsMenuMaxHeight] = useState<number | 'auto'>('auto');
+    const [tagsMenuMaxHeight, setTagsMenuMaxHeight] =
+      useState<number | 'auto'>('auto');
 
     const toggleOn = (condition: (note: SNNote) => boolean) => {
       const notesMatchingAttribute = notes.filter(condition);
@@ -62,24 +67,27 @@ export const NotesOptions = observer(
       const defaultFontSize = window.getComputedStyle(
         document.documentElement
       ).fontSize;
-      const maxTagsMenuSize = parseFloat(defaultFontSize) * 20;
-      const { clientWidth, clientHeight } = document.body;
+      const maxTagsMenuSize = parseFloat(defaultFontSize) * 30;
+      const { clientWidth, clientHeight } = document.documentElement;
       const buttonRect = tagsButtonRef.current.getBoundingClientRect();
-      const { offsetTop, offsetWidth } = tagsButtonRef.current;
       const footerHeight = 32;
 
-      if (buttonRect.top + maxTagsMenuSize > clientHeight - footerHeight) {
+      if ((buttonRect.top + maxTagsMenuSize) > (clientHeight - footerHeight)) {
         setTagsMenuMaxHeight(clientHeight - buttonRect.top - footerHeight - 2);
       }
 
-      setTagsMenuPosition({
-        top: offsetTop,
-        right:
-          buttonRect.right + maxTagsMenuSize >
-          clientWidth
-            ? offsetWidth
-            : -offsetWidth,
-      });
+      if ((buttonRect.right + maxTagsMenuSize) > clientWidth) {
+        setTagsMenuPosition({
+          top: buttonRect.top,
+          right: clientWidth - buttonRect.left,
+        });
+      } else {
+        setTagsMenuPosition({
+          top: buttonRect.top,
+          left: buttonRect.right,
+        });
+      }
+
 
       setTagsMenuOpen(!tagsMenuOpen);
     };
@@ -127,10 +135,7 @@ export const NotesOptions = observer(
         </Switch>
         <div className="h-1px my-2 bg-border"></div>
         {appState.tags.tagsCount > 0 && (
-          <Disclosure
-            open={tagsMenuOpen}
-            onChange={openTagsMenu}
-          >
+          <Disclosure open={tagsMenuOpen} onChange={openTagsMenu}>
             <DisclosureButton
               onKeyUp={(event) => {
                 if (event.key === 'Escape') {
@@ -145,10 +150,7 @@ export const NotesOptions = observer(
                 <Icon type="hashtag" className={iconClass} />
                 {'Add tag'}
               </div>
-              <Icon
-                type="chevron-right"
-                className="color-neutral"
-              />
+              <Icon type="chevron-right" className="color-neutral" />
             </DisclosureButton>
             <DisclosurePanel
               onKeyUp={(event) => {
@@ -160,8 +162,9 @@ export const NotesOptions = observer(
               style={{
                 ...tagsMenuPosition,
                 maxHeight: tagsMenuMaxHeight,
+                position: 'fixed',
               }}
-              className="sn-dropdown sn-dropdown-anchor-right flex flex-col py-2 max-h-80 absolute overflow-y-scroll"
+              className="sn-dropdown flex flex-col py-2 max-h-120 max-w-80 fixed overflow-y-scroll"
             >
               {appState.tags.tags.map((tag) => (
                 <button
@@ -278,10 +281,7 @@ export const NotesOptions = observer(
               }}
             >
               <div className="flex items-start">
-                <Icon
-                  type="trash-sweep"
-                  className="color-danger mr-2"
-                />
+                <Icon type="trash-sweep" className="color-danger mr-2" />
                 <div className="flex-row">
                   <div className="color-danger">Empty Trash</div>
                   <div className="text-xs">
diff --git a/app/assets/javascripts/components/NotesOptionsPanel.tsx b/app/assets/javascripts/components/NotesOptionsPanel.tsx
index 147010d02..93299f2d4 100644
--- a/app/assets/javascripts/components/NotesOptionsPanel.tsx
+++ b/app/assets/javascripts/components/NotesOptionsPanel.tsx
@@ -21,6 +21,7 @@ export const NotesOptionsPanel = observer(({ appState }: Props) => {
     top: 0,
     right: 0,
   });
+  const [maxHeight, setMaxHeight] = useState<number | 'auto'>('auto');
   const buttonRef = useRef<HTMLButtonElement>();
   const panelRef = useRef<HTMLDivElement>();
   const [closeOnBlur] = useCloseOnBlur(panelRef, setOpen);
@@ -35,6 +36,9 @@ export const NotesOptionsPanel = observer(({ appState }: Props) => {
       open={open}
       onChange={() => {
         const rect = buttonRef.current.getBoundingClientRect();
+        const { clientHeight } = document.documentElement;
+        const footerHeight = 32;
+        setMaxHeight(clientHeight - rect.bottom - footerHeight - 2);
         setPosition({
           top: rect.bottom,
           right: document.body.clientWidth - rect.right,
@@ -65,8 +69,9 @@ export const NotesOptionsPanel = observer(({ appState }: Props) => {
           ref={panelRef}
           style={{
             ...position,
+            maxHeight
           }}
-          className="sn-dropdown flex flex-col py-2"
+          className="sn-dropdown max-h-120 max-w-80 flex flex-col py-2 overflow-y-scroll fixed"
         >
           {open && (
             <NotesOptions
diff --git a/app/assets/javascripts/components/SearchOptions.tsx b/app/assets/javascripts/components/SearchOptions.tsx
index 7edad0eb2..193515ede 100644
--- a/app/assets/javascripts/components/SearchOptions.tsx
+++ b/app/assets/javascripts/components/SearchOptions.tsx
@@ -63,7 +63,7 @@ const SearchOptions = observer(({ appState }: Props) => {
         style={{
           top: optionsPanelTop,
         }}
-        className="sn-dropdown sn-dropdown-anchor-right grid gap-2 py-2"
+        className="sn-dropdown sn-dropdown-anchor-right absolute grid gap-2 py-2"
       >
         <Switch
           className="h-10"
diff --git a/app/assets/javascripts/ui_models/app_state/notes_state.ts b/app/assets/javascripts/ui_models/app_state/notes_state.ts
index 7570d0262..6688e4e97 100644
--- a/app/assets/javascripts/ui_models/app_state/notes_state.ts
+++ b/app/assets/javascripts/ui_models/app_state/notes_state.ts
@@ -27,6 +27,7 @@ export class NotesState {
     top: 0,
     left: 0,
   };
+  contextMenuMaxHeight: number | 'auto' = 'auto';
   showProtectedWarning = false;
 
   constructor(
@@ -45,6 +46,7 @@ export class NotesState {
 
       setContextMenuOpen: action,
       setContextMenuPosition: action,
+      setContextMenuMaxHeight: action,
       setShowProtectedWarning: action,
       unselectNotes: action,
     });
@@ -181,6 +183,10 @@ export class NotesState {
     this.contextMenuPosition = position;
   }
 
+  setContextMenuMaxHeight(maxHeight: number | 'auto'): void {
+    this.contextMenuMaxHeight = maxHeight;
+  }
+
   async changeSelectedNotes(
     mutate: (mutator: NoteMutator) => void
   ): Promise<void> {
diff --git a/app/assets/javascripts/views/notes/notes_view.ts b/app/assets/javascripts/views/notes/notes_view.ts
index fc8c8b15c..cfbbaf40b 100644
--- a/app/assets/javascripts/views/notes/notes_view.ts
+++ b/app/assets/javascripts/views/notes/notes_view.ts
@@ -308,12 +308,16 @@ class NotesViewCtrl extends PureViewCtrl<unknown, NotesCtrlState> {
       await this.selectNote(note);
     }
     if (this.state.selectedNotes[note.uuid]) {
-      const clientHeight = document.documentElement.clientHeight;
+      const { clientHeight } = document.documentElement;
       const defaultFontSize = window.getComputedStyle(
         document.documentElement
       ).fontSize;
-      const maxContextMenuHeight = parseFloat(defaultFontSize) * 20;
+      const maxContextMenuHeight = parseFloat(defaultFontSize) * 30;
       const footerHeight = 32;
+
+      // Open up-bottom is default behavior
+      let openUpBottom = true;
+
       const bottomSpace = clientHeight - footerHeight - e.clientY;
       const upSpace = e.clientY;
 
@@ -321,23 +325,41 @@ class NotesViewCtrl extends PureViewCtrl<unknown, NotesCtrlState> {
       if (maxContextMenuHeight > bottomSpace) {
         // If there's enough space, open bottom-up
         if (upSpace > maxContextMenuHeight) {
-          this.appState.notes.setContextMenuPosition({
-            bottom: clientHeight - e.clientY,
-            left: e.clientX,
-          });
-        // Else, open on top of screen
+          openUpBottom = false;
+          this.appState.notes.setContextMenuMaxHeight(
+            'auto'
+          );
+        // Else, reduce max height (menu will be scrollable) and open in whichever direction there's more space
         } else {
-          this.appState.notes.setContextMenuPosition({
-            top: 2,
-            left: e.clientX,
-          });
+          if (upSpace > bottomSpace) {
+            this.appState.notes.setContextMenuMaxHeight(
+              upSpace - 2
+            );
+            openUpBottom = false;
+          } else {
+            this.appState.notes.setContextMenuMaxHeight(
+              bottomSpace - 2
+            );
+          }
         }
       } else {
+        this.appState.notes.setContextMenuMaxHeight(
+          'auto'
+        );
+      }
+
+      if (openUpBottom) {
         this.appState.notes.setContextMenuPosition({
           top: e.clientY,
           left: e.clientX,
         });
+      } else {
+        this.appState.notes.setContextMenuPosition({
+          bottom: clientHeight - e.clientY,
+          left: e.clientX,
+        });
       }
+
       this.appState.notes.setContextMenuOpen(true);
     }
   }
diff --git a/app/assets/stylesheets/_sn.scss b/app/assets/stylesheets/_sn.scss
index 253373108..0218f6905 100644
--- a/app/assets/stylesheets/_sn.scss
+++ b/app/assets/stylesheets/_sn.scss
@@ -127,6 +127,10 @@
   max-width: 15rem;
 }
 
+.max-w-80 {
+  max-width: 20rem;
+}
+
 .h-1px {
   height: 1px;
 }
@@ -151,8 +155,12 @@
   height: 2.5rem;
 }
 
-.max-h-80 {
-  max-height: 20rem;
+.max-h-120 {
+  max-height: 30rem;
+}
+
+.fixed {
+  position: fixed;
 }
 
 .overflow-y-scroll {
@@ -198,7 +206,6 @@
 }
 
 .sn-dropdown {
-  @extend .absolute;
   @extend .bg-default;
   @extend .min-w-80;
   @extend .transition-transform;