diff --git a/client/common/Tooltip.tsx b/client/common/Tooltip.tsx
new file mode 100644
index 0000000000..f5e5778c3d
--- /dev/null
+++ b/client/common/Tooltip.tsx
@@ -0,0 +1,79 @@
+import React, { ReactElement, useRef, useState } from 'react';
+
+export type TooltipDirection = 'n' | 's' | 'e' | 'w';
+
+export type TooltipProps = {
+  content: string;
+  direction?: TooltipDirection;
+  noDelay?: boolean;
+  children: ReactElement;
+};
+
+export function Tooltip({
+  content,
+  direction = 'n',
+  noDelay = false,
+  children
+}: TooltipProps) {
+  const [open, setOpen] = useState(false);
+  const tooltipIdRef = useRef(`tooltip-${Math.random().toString(36).slice(2)}`);
+
+  const childProps: Record<string, unknown> = {
+    'aria-label': content,
+    className: [
+      (children.props && children.props.className) || '',
+      'tooltipped',
+      `tooltipped-${direction}`,
+      noDelay ? 'tooltipped-no-delay' : ''
+    ]
+      .filter(Boolean)
+      .join(' '),
+    'aria-describedby': tooltipIdRef.current,
+    onFocus: (e: React.FocusEvent) => {
+      setOpen(true);
+      if (children.props && typeof children.props.onFocus === 'function') {
+        children.props.onFocus(e);
+      }
+    },
+    onBlur: (e: React.FocusEvent) => {
+      setOpen(false);
+      if (children.props && typeof children.props.onBlur === 'function') {
+        children.props.onBlur(e);
+      }
+    },
+    onMouseEnter: (e: React.MouseEvent) => {
+      setOpen(true);
+      if (children.props && typeof children.props.onMouseEnter === 'function') {
+        children.props.onMouseEnter(e);
+      }
+    },
+    onMouseLeave: (e: React.MouseEvent) => {
+      setOpen(false);
+      if (children.props && typeof children.props.onMouseLeave === 'function') {
+        children.props.onMouseLeave(e);
+      }
+    },
+    onKeyDown: (e: React.KeyboardEvent) => {
+      if (e.key === 'Escape') {
+        setOpen(false);
+        (e.target as HTMLElement)?.blur();
+      }
+      if (children.props && typeof children.props.onKeyDown === 'function') {
+        children.props.onKeyDown(e);
+      }
+    }
+  };
+
+  const trigger = React.cloneElement(children, childProps);
+
+  return (
+    <span className="tooltip-wrapper">
+      {trigger}
+      {open && (
+        <span id={tooltipIdRef.current} role="tooltip" className="sr-only">
+          {content}
+        </span>
+      )}
+    </span>
+  );
+}
diff --git a/client/components/Menubar/MenubarItem.tsx b/client/components/Menubar/MenubarItem.tsx
index d2b3a1b1a3..9b69d24304 100644
--- a/client/components/Menubar/MenubarItem.tsx
+++ b/client/components/Menubar/MenubarItem.tsx
@@ -1,6 +1,7 @@
 import React, { useEffect, useContext, useRef } from 'react';
 import { MenubarContext, SubmenuContext, ParentMenuContext } from './contexts';
 import { ButtonOrLink, ButtonOrLinkProps } from '../../common/ButtonOrLink';
+import { Tooltip, TooltipDirection } from '../../common/Tooltip';
 
 export enum MenubarItemRole {
   MENU_ITEM = 'menuitem',
@@ -13,6 +14,8 @@ export interface MenubarItemProps extends Omit<ButtonOrLinkProps, 'role'> {
    */
   role?: MenubarItemRole;
   selected?: boolean;
+  tooltipContent?: string;
+  tooltipDirection?: TooltipDirection;
 }
 
 /**
@@ -54,6 +57,8 @@ export function MenubarItem({
   role: customRole = MenubarItemRole.MENU_ITEM,
   isDisabled = false,
   selected = false,
+  tooltipContent,
+  tooltipDirection,
   ...rest
 }: MenubarItemProps) {
   const { createMenuItemHandlers, hasFocus } = useContext(MenubarContext);
@@ -86,6 +91,26 @@ export function MenubarItem({
     return unregister;
   }, [submenuItems, registerSubmenuItem]);
 
+  const buttonOrLink = (
+    <ButtonOrLink
+      {...rest}
+      {...handlers}
+      {...ariaSelected}
+      role={role}
+      tabIndex={-1}
+      id={id}
+      isDisabled={isDisabled}
+    />
+  );
+
+  const content = tooltipContent ? (
+    <Tooltip content={tooltipContent} direction={tooltipDirection}>
+      {buttonOrLink}
+    </Tooltip>
+  ) : (
+    buttonOrLink
+  );
+
   return (
     <li
       className={`${className} ${
@@ -94,15 +119,7 @@ export function MenubarItem({
       ref={menuItemRef}
       onMouseEnter={handleMouseEnter}
     >
-      <ButtonOrLink
-        {...rest}
-        {...handlers}
-        {...ariaSelected}
-        role={role}
-        tabIndex={-1}
-        id={id}
-        isDisabled={isDisabled}
-      />
+      {content}
     </li>
   );
 }
diff --git a/client/modules/IDE/components/Header/Nav.jsx b/client/modules/IDE/components/Header/Nav.jsx
index 28995a2d56..48e0935ae9 100644
--- a/client/modules/IDE/components/Header/Nav.jsx
+++ b/client/modules/IDE/components/Header/Nav.jsx
@@ -185,7 +185,12 @@ const ProjectMenu = () => {
           isDisabled={
             !user.authenticated ||
             !isLoginEnabled ||
-            (project?.owner && !isUserOwner)
+            (!!project?.owner && !isUserOwner)
+          }
+          tooltipContent={
+            !user.authenticated || !isLoginEnabled
+              ? t('Nav.File.SaveTooltipUnauthenticated')
+              : undefined
           }
           onClick={() => saveSketch(cmRef.current)}
         >
@@ -194,7 +199,12 @@ const ProjectMenu = () => {
         </MenubarItem>
         <MenubarItem
           id="file-duplicate"
-          isDisabled={isUnsaved || !user.authenticated}
+          isDisabled={!user.authenticated || isUnsaved}
+          tooltipContent={
+            !user.authenticated
+              ? t('Nav.File.DuplicateTooltipUnauthenticated')
+              : undefined
+          }
           onClick={() => dispatch(cloneProject())}
         >
           {t('Nav.File.Duplicate')}
@@ -202,6 +212,9 @@ const ProjectMenu = () => {
         <MenubarItem
           id="file-share"
           isDisabled={isUnsaved}
+          tooltipContent={
+            isUnsaved ? t('Nav.File.ShareTooltipUnsaved') : undefined
+          }
           onClick={shareSketch}
         >
           {t('Nav.File.Share')}
@@ -209,6 +222,9 @@ const ProjectMenu = () => {
         <MenubarItem
           id="file-download"
           isDisabled={isUnsaved}
+          tooltipContent={
+            isUnsaved ? t('Nav.File.DownloadTooltipUnsaved') : undefined
+          }
           onClick={downloadSketch}
         >
           {t('Nav.File.Download')}
@@ -216,6 +232,11 @@ const ProjectMenu = () => {
         <MenubarItem
           id="file-open"
           isDisabled={!user.authenticated}
+          tooltipContent={
+            !user.authenticated
+              ? t('Nav.File.OpenTooltipUnauthenticated')
+              : undefined
+          }
           href={`/${user.username}/sketches`}
         >
           {t('Nav.File.Open')}
@@ -223,7 +244,12 @@ const ProjectMenu = () => {
         <MenubarItem
           id="file-add-to-collection"
           isDisabled={
-            !isUiCollectionsEnabled || !user.authenticated || isUnsaved
+            !user.authenticated || !isUiCollectionsEnabled || isUnsaved
+          }
+          tooltipContent={
+            !user.authenticated
+              ? t('Nav.File.AddToCollectionTooltipUnauthenticated')
+              : undefined
           }
           href={`/${user.username}/sketches/${project?.id}/add-to-collection`}
         >
diff --git a/client/modules/IDE/components/Sidebar.jsx b/client/modules/IDE/components/Sidebar.jsx
index 24fd487c9a..a7f6169bf3 100644
--- a/client/modules/IDE/components/Sidebar.jsx
+++ b/client/modules/IDE/components/Sidebar.jsx
@@ -16,6 +16,7 @@ import { getAuthenticated, selectCanEditSketch } from '../selectors/users';
 import ConnectedFileNode from './FileNode';
 import { PlusIcon } from '../../../common/icons';
 import { FileDrawer } from './Editor/MobileEditor';
+import { Tooltip } from '../../../common/Tooltip';
 
 // TODO: use a generic Dropdown UI component
 
@@ -124,8 +125,8 @@ export default function SideBar() {
                     {t('Sidebar.AddFile')}
                   </button>
                 </li>
-                {isAuthenticated && (
-                  <li>
+                <li>
+                  {isAuthenticated ? (
                     <button
                       aria-label={t('Sidebar.UploadFileARIA')}
                       onClick={() => {
@@ -135,8 +136,25 @@ export default function SideBar() {
                     >
                       {t('Sidebar.UploadFile')}
                     </button>
-                  </li>
-                )}
+                  ) : (
+                    <Tooltip
+                      content={t('Sidebar.UploadFileTooltipUnauthenticated')}
+                      direction="n"
+                    >
+                      <button
+                        aria-label={t('Sidebar.UploadFileARIA')}
+                        aria-disabled
+                        onClick={(e) => {
+                          // prevent any action when unauthenticated
+                          e.preventDefault();
+                          e.stopPropagation();
+                        }}
+                      >
+                        {t('Sidebar.UploadFile')}
+                      </button>
+                    </Tooltip>
+                  )}
+                </li>
               </ul>
             )}
           </div>
diff --git a/client/styles/components/_nav.scss b/client/styles/components/_nav.scss
index 5d597596ac..dfd08cf4c2 100644
--- a/client/styles/components/_nav.scss
+++ b/client/styles/components/_nav.scss
@@ -174,8 +174,8 @@
 .nav__dropdown {
   @extend %dropdown-open-left;
   display: none;
-  max-height: 60vh;
-  overflow-y: auto;
+  max-height: none;
+  overflow: visible;
   .nav__item--open & {
     display: flex;
   }
@@ -253,6 +253,7 @@
 .nav__keyboard-shortcut {
   font-size: #{math.div(12, $base-font-size)}rem;
   font-family: Inconsololata, monospace;
+  margin-left: auto;
 
   @include themify() {
     color: getThemifyVariable('keyboard-shortcut-color');
diff --git a/client/styles/components/_tooltip.scss b/client/styles/components/_tooltip.scss
new file mode 100644
index 0000000000..d4249fc443
--- /dev/null
+++ b/client/styles/components/_tooltip.scss
@@ -0,0 +1,31 @@
+.tooltip-wrapper {
+  position: relative;
+  display: inline-flex;
+}
+
+.tooltip-wrapper .tooltipped::after {
+  @include themify() {
+    background-color: getThemifyVariable('button-background-hover-color');
+    color: getThemifyVariable('button-hover-color');
+  }
+  font-family: Montserrat, sans-serif;
+  font-size: 1rem;
+  padding: 0.5rem 0.75rem;
+  max-width: none;
+  white-space: nowrap;
+  left: 1rem;
+  right: auto;
+  transform: translateX(0);
+  text-align: left;
+}
+
+.tooltip-wrapper .tooltipped-n::before,
+.tooltip-wrapper .tooltipped::before {
+  @include themify() {
+    color: getThemifyVariable('button-background-hover-color');
+    border-top-color: getThemifyVariable('button-background-hover-color');
+  }
+  left: 1.75rem;
+  right: auto;
+  transform: translateX(0);
+}
diff --git a/client/styles/main.scss b/client/styles/main.scss
index 3792c192f1..400da75bfb 100644
--- a/client/styles/main.scss
+++ b/client/styles/main.scss
@@ -58,6 +58,7 @@
 @import 'components/admonition';
 @import 'components/banner';
 @import 'components/visibility-dropdown';
+@import 'components/tooltip';
 
 @import 'layout/dashboard';
 @import 'layout/ide';
\ No newline at end of file
diff --git a/translations/locales/en-US/translations.json b/translations/locales/en-US/translations.json
index 1d254a5afc..3198d1a42e 100644
--- a/translations/locales/en-US/translations.json
+++ b/translations/locales/en-US/translations.json
@@ -8,7 +8,13 @@
       "Open": "Open",
       "Download": "Download",
       "AddToCollection": "Add to Collection",
-      "Examples": "Examples"
+      "Examples": "Examples",
+      "SaveTooltipUnauthenticated": "Log in to save your sketch",
+      "DuplicateTooltipUnauthenticated": "Log in to duplicate this sketch",
+      "OpenTooltipUnauthenticated": "Log in to open your sketches",
+      "AddToCollectionTooltipUnauthenticated": "Log in to add to collections",
+      "ShareTooltipUnsaved": "Save your sketch before sharing",
+      "DownloadTooltipUnsaved": "Save your sketch before downloading"
     },
     "Edit": {
       "Title": "Edit",
@@ -275,7 +281,8 @@
     "AddFile": "Create file",
     "AddFileARIA": "add file",
     "UploadFile": "Upload file",
-    "UploadFileARIA": "upload file"
+    "UploadFileARIA": "upload file",
+    "UploadFileTooltipUnauthenticated": "Log in to upload files"
   },
   "FileNode": {
     "OpenFolderARIA": "Open folder contents",