diff --git a/packages/web/src/javascripts/Components/SuperEditor/Plugins/FloatingLinkEditorPlugin/LinkEditor.tsx b/packages/web/src/javascripts/Components/SuperEditor/Plugins/FloatingLinkEditorPlugin/LinkEditor.tsx
index a3d37c45d..1997ba297 100644
--- a/packages/web/src/javascripts/Components/SuperEditor/Plugins/FloatingLinkEditorPlugin/LinkEditor.tsx
+++ b/packages/web/src/javascripts/Components/SuperEditor/Plugins/FloatingLinkEditorPlugin/LinkEditor.tsx
@@ -6,6 +6,7 @@ import { sanitizeUrl } from '../../Lexical/Utils/sanitizeUrl'
 import { TOGGLE_LINK_COMMAND } from '@lexical/link'
 import { useCallback, useState } from 'react'
 import { GridSelection, LexicalEditor, NodeSelection, RangeSelection } from 'lexical'
+import { classNames } from '@standardnotes/snjs'
 
 type Props = {
   linkUrl: string
@@ -13,9 +14,10 @@ type Props = {
   setEditMode: (isEditMode: boolean) => void
   editor: LexicalEditor
   lastSelection: RangeSelection | GridSelection | NodeSelection | null
+  isAutoLink: boolean
 }
 
-const LinkEditor = ({ linkUrl, isEditMode, setEditMode, editor, lastSelection }: Props) => {
+const LinkEditor = ({ linkUrl, isEditMode, setEditMode, editor, lastSelection, isAutoLink }: Props) => {
   const [editedLinkUrl, setEditedLinkUrl] = useState('')
 
   const handleLinkSubmission = () => {
@@ -80,7 +82,10 @@ const LinkEditor = ({ linkUrl, isEditMode, setEditMode, editor, lastSelection }:
   ) : (
     <div className="flex items-center gap-1">
       <a
-        className="mr-1 flex flex-grow items-center gap-2 overflow-hidden whitespace-nowrap underline"
+        className={classNames(
+          'mr-1 flex flex-grow items-center gap-2 overflow-hidden whitespace-nowrap underline',
+          isAutoLink && 'py-2.5',
+        )}
         href={linkUrl}
         target="_blank"
         rel="noopener noreferrer"
@@ -88,31 +93,35 @@ const LinkEditor = ({ linkUrl, isEditMode, setEditMode, editor, lastSelection }:
         <Icon type="open-in" className="ml-1 flex-shrink-0" />
         <div className="max-w-[35ch] overflow-hidden text-ellipsis">{linkUrl}</div>
       </a>
-      <button
-        className="flex rounded-lg p-3 hover:bg-contrast hover:text-text disabled:cursor-not-allowed"
-        onClick={() => {
-          setEditedLinkUrl(linkUrl)
-          setEditMode(true)
-        }}
-        aria-label="Edit link"
-        onMouseDown={(event) => event.preventDefault()}
-      >
-        <IconComponent size={15}>
-          <PencilFilledIcon />
-        </IconComponent>
-      </button>
-      <button
-        className="flex rounded-lg p-3 hover:bg-contrast hover:text-text disabled:cursor-not-allowed"
-        onClick={() => {
-          editor.dispatchCommand(TOGGLE_LINK_COMMAND, null)
-        }}
-        aria-label="Remove link"
-        onMouseDown={(event) => event.preventDefault()}
-      >
-        <IconComponent size={15}>
-          <TrashFilledIcon />
-        </IconComponent>
-      </button>
+      {!isAutoLink && (
+        <>
+          <button
+            className="flex rounded-lg p-3 hover:bg-contrast hover:text-text disabled:cursor-not-allowed"
+            onClick={() => {
+              setEditedLinkUrl(linkUrl)
+              setEditMode(true)
+            }}
+            aria-label="Edit link"
+            onMouseDown={(event) => event.preventDefault()}
+          >
+            <IconComponent size={15}>
+              <PencilFilledIcon />
+            </IconComponent>
+          </button>
+          <button
+            className="flex rounded-lg p-3 hover:bg-contrast hover:text-text disabled:cursor-not-allowed"
+            onClick={() => {
+              editor.dispatchCommand(TOGGLE_LINK_COMMAND, null)
+            }}
+            aria-label="Remove link"
+            onMouseDown={(event) => event.preventDefault()}
+          >
+            <IconComponent size={15}>
+              <TrashFilledIcon />
+            </IconComponent>
+          </button>
+        </>
+      )}
     </div>
   )
 }
diff --git a/packages/web/src/javascripts/Components/SuperEditor/Plugins/FloatingLinkEditorPlugin/index.tsx b/packages/web/src/javascripts/Components/SuperEditor/Plugins/FloatingLinkEditorPlugin/index.tsx
index fa7476dc2..71fa94369 100644
--- a/packages/web/src/javascripts/Components/SuperEditor/Plugins/FloatingLinkEditorPlugin/index.tsx
+++ b/packages/web/src/javascripts/Components/SuperEditor/Plugins/FloatingLinkEditorPlugin/index.tsx
@@ -28,7 +28,15 @@ import { getPositionedPopoverStyles } from '@/Components/Popover/GetPositionedPo
 import { getAdjustedStylesForNonPortalPopover } from '@/Components/Popover/Utils/getAdjustedStylesForNonPortal'
 import LinkEditor from './LinkEditor'
 
-function FloatingLinkEditor({ editor, anchorElem }: { editor: LexicalEditor; anchorElem: HTMLElement }): JSX.Element {
+function FloatingLinkEditor({
+  editor,
+  anchorElem,
+  isAutoLink,
+}: {
+  editor: LexicalEditor
+  anchorElem: HTMLElement
+  isAutoLink: boolean
+}): JSX.Element {
   const editorRef = useRef<HTMLDivElement | null>(null)
   const [linkUrl, setLinkUrl] = useState('')
   const [isEditMode, setEditMode] = useState(false)
@@ -154,6 +162,7 @@ function FloatingLinkEditor({ editor, anchorElem }: { editor: LexicalEditor; anc
         setEditMode={setEditMode}
         editor={editor}
         lastSelection={lastSelection}
+        isAutoLink={isAutoLink}
       />
     </div>
   )
@@ -162,6 +171,7 @@ function FloatingLinkEditor({ editor, anchorElem }: { editor: LexicalEditor; anc
 function useFloatingLinkEditorToolbar(editor: LexicalEditor, anchorElem: HTMLElement): JSX.Element | null {
   const [activeEditor, setActiveEditor] = useState(editor)
   const [isLink, setIsLink] = useState(false)
+  const [isAutoLink, setIsAutoLink] = useState(false)
 
   const updateToolbar = useCallback(() => {
     const selection = $getSelection()
@@ -170,11 +180,17 @@ function useFloatingLinkEditorToolbar(editor: LexicalEditor, anchorElem: HTMLEle
       const linkParent = $findMatchingParent(node, $isLinkNode)
       const autoLinkParent = $findMatchingParent(node, $isAutoLinkNode)
 
-      if (linkParent != null && autoLinkParent == null) {
+      if (linkParent != null) {
         setIsLink(true)
       } else {
         setIsLink(false)
       }
+
+      if (autoLinkParent != null) {
+        setIsAutoLink(true)
+      } else {
+        setIsAutoLink(false)
+      }
     }
   }, [])
 
@@ -197,7 +213,12 @@ function useFloatingLinkEditorToolbar(editor: LexicalEditor, anchorElem: HTMLEle
     )
   }, [editor, updateToolbar])
 
-  return isLink ? createPortal(<FloatingLinkEditor editor={activeEditor} anchorElem={anchorElem} />, anchorElem) : null
+  return isLink
+    ? createPortal(
+        <FloatingLinkEditor editor={activeEditor} anchorElem={anchorElem} isAutoLink={isAutoLink} />,
+        anchorElem,
+      )
+    : null
 }
 
 export default function FloatingLinkEditorPlugin({
diff --git a/packages/web/src/javascripts/Components/SuperEditor/Plugins/FloatingTextFormatToolbarPlugin/index.tsx b/packages/web/src/javascripts/Components/SuperEditor/Plugins/FloatingTextFormatToolbarPlugin/index.tsx
index c707d3a8f..18fadaae9 100644
--- a/packages/web/src/javascripts/Components/SuperEditor/Plugins/FloatingTextFormatToolbarPlugin/index.tsx
+++ b/packages/web/src/javascripts/Components/SuperEditor/Plugins/FloatingTextFormatToolbarPlugin/index.tsx
@@ -7,7 +7,7 @@
  */
 
 import { $isCodeHighlightNode } from '@lexical/code'
-import { $isLinkNode, TOGGLE_LINK_COMMAND } from '@lexical/link'
+import { $isLinkNode, $isAutoLinkNode, TOGGLE_LINK_COMMAND } from '@lexical/link'
 import { useLexicalComposerContext } from '@lexical/react/LexicalComposerContext'
 import { mergeRegister, $findMatchingParent, $getNearestNodeOfType } from '@lexical/utils'
 import {
@@ -92,6 +92,7 @@ function TextFormatFloatingToolbar({
   anchorElem,
   isText,
   isLink,
+  isAutoLink,
   isBold,
   isItalic,
   isUnderline,
@@ -109,6 +110,7 @@ function TextFormatFloatingToolbar({
   isCode: boolean
   isItalic: boolean
   isLink: boolean
+  isAutoLink: boolean
   isStrikethrough: boolean
   isSubscript: boolean
   isSuperscript: boolean
@@ -276,6 +278,7 @@ function TextFormatFloatingToolbar({
           linkUrl={linkUrl}
           isEditMode={isLinkEditMode}
           setEditMode={setIsLinkEditMode}
+          isAutoLink={isAutoLink}
           editor={editor}
           lastSelection={lastSelection}
         />
@@ -387,6 +390,7 @@ function useFloatingTextFormatToolbar(editor: LexicalEditor, anchorElem: HTMLEle
   const [activeEditor, setActiveEditor] = useState(editor)
   const [isText, setIsText] = useState(false)
   const [isLink, setIsLink] = useState(false)
+  const [isAutoLink, setIsAutoLink] = useState(false)
   const [isBold, setIsBold] = useState(false)
   const [isItalic, setIsItalic] = useState(false)
   const [isUnderline, setIsUnderline] = useState(false)
@@ -471,6 +475,11 @@ function useFloatingTextFormatToolbar(editor: LexicalEditor, anchorElem: HTMLEle
       } else {
         setIsLink(false)
       }
+      if ($isAutoLinkNode(parent) || $isAutoLinkNode(node)) {
+        setIsAutoLink(true)
+      } else {
+        setIsAutoLink(false)
+      }
 
       if (!$isCodeHighlightNode(selection.anchor.getNode()) && selection.getTextContent() !== '') {
         setIsText($isTextNode(node))
@@ -515,6 +524,7 @@ function useFloatingTextFormatToolbar(editor: LexicalEditor, anchorElem: HTMLEle
       anchorElem={anchorElem}
       isText={isText}
       isLink={isLink}
+      isAutoLink={isAutoLink}
       isBold={isBold}
       isItalic={isItalic}
       isStrikethrough={isStrikethrough}