diff --git a/packages/core/src/lib/hooks/useMediaInsert.ts b/packages/core/src/lib/hooks/useMediaInsert.ts
index bb1c3d9f..8e755a2b 100644
--- a/packages/core/src/lib/hooks/useMediaInsert.ts
+++ b/packages/core/src/lib/hooks/useMediaInsert.ts
@@ -1,4 +1,4 @@
-import { useCallback, useEffect, useMemo, useState } from 'react';
+import { useCallback, useEffect, useMemo } from 'react';
 import { v4 as uuid } from 'uuid';
 
 import { openMediaLibrary, removeInsertedMedia } from '@staticcms/core/actions/mediaLibrary';
@@ -39,17 +39,15 @@ export default function useMediaInsert<T extends string | string[], F extends Me
   const finalControlID = useMemo(() => controlID ?? uuid(), [controlID]);
   const mediaPathSelector = useMemo(() => selectMediaPath(finalControlID), [finalControlID]);
   const mediaPath = useAppSelector(mediaPathSelector);
-  const [selected, setSelected] = useState(false);
 
   useEffect(() => {
-    if (!selected && mediaPath && (mediaPath.path !== value.path || mediaPath.alt !== value.alt)) {
-      setSelected(true);
+    if (mediaPath && (mediaPath.path !== value.path || mediaPath.alt !== value.alt)) {
       setTimeout(() => {
         callback(mediaPath as MediaPath<T>);
         dispatch(removeInsertedMedia(finalControlID));
       });
     }
-  }, [callback, finalControlID, dispatch, mediaPath, value, selected]);
+  }, [callback, finalControlID, dispatch, mediaPath, value]);
 
   const handleOpenMediaLibrary = useCallback(
     (e?: MouseEvent, { replaceIndex }: { replaceIndex?: number } = {}) => {
@@ -69,7 +67,6 @@ export default function useMediaInsert<T extends string | string[], F extends Me
           insertOptions,
         }),
       );
-      setSelected(false);
     },
     [
       dispatch,
diff --git a/packages/core/src/lib/util/path.ts b/packages/core/src/lib/util/path.ts
index 7353d2ea..b90107c8 100644
--- a/packages/core/src/lib/util/path.ts
+++ b/packages/core/src/lib/util/path.ts
@@ -1,4 +1,4 @@
-const absolutePath = new RegExp('^(?:[a-z]+:)?//', 'i');
+const absolutePath = new RegExp('^(?:(?:[a-z]+:)?//)|(?:mailto:)|(?:tel:)', 'i');
 
 function normalizePath(path: string) {
   return path.replace(/[\\/]+/g, '/');
diff --git a/packages/core/src/widgets/markdown/plate/components/balloon-toolbar/BalloonToolbar.tsx b/packages/core/src/widgets/markdown/plate/components/balloon-toolbar/BalloonToolbar.tsx
index 755736a7..12ebda08 100644
--- a/packages/core/src/widgets/markdown/plate/components/balloon-toolbar/BalloonToolbar.tsx
+++ b/packages/core/src/widgets/markdown/plate/components/balloon-toolbar/BalloonToolbar.tsx
@@ -249,42 +249,44 @@ const BalloonToolbar: FC<BalloonToolbarProps> = ({
           left: `${selectionBoundingClientRect?.x}px`,
         }}
       />
-      <PopperUnstyled
-        open={Boolean(debouncedOpen && anchorEl.current)}
-        component="div"
-        placement="top"
-        anchorEl={anchorEl.current ?? null}
-        onFocus={handleFocus}
-        onBlur={handleBlur}
-        tabIndex={0}
-        className="
-          absolute
-          max-h-60
-          overflow-auto
-          rounded-md
-          bg-white
-          p-1
-          text-base
-          shadow-lg
-          ring-1
-          ring-black
-          ring-opacity-5
-          focus:outline-none
-          sm:text-sm
-          z-40
-          dark:bg-slate-700
-        "
-      >
-        <div
-          data-testid="balloon-toolbar"
+      {groups.length > 0 || debouncedGroups.length > 0 ? (
+        <PopperUnstyled
+          open={Boolean(debouncedOpen && anchorEl.current)}
+          component="div"
+          placement="top"
+          anchorEl={anchorEl.current ?? null}
+          onFocus={handleFocus}
+          onBlur={handleBlur}
+          tabIndex={0}
           className="
-            flex
-            gap-0.5
+            absolute
+            max-h-60
+            overflow-auto
+            rounded-md
+            bg-white
+            p-1
+            text-base
+            shadow-lg
+            ring-1
+            ring-black
+            ring-opacity-5
+            focus:outline-none
+            sm:text-sm
+            z-40
+            dark:bg-slate-700
           "
         >
-          {groups.length > 0 ? groups : debouncedGroups}
-        </div>
-      </PopperUnstyled>
+          <div
+            data-testid="balloon-toolbar"
+            className="
+              flex
+              gap-0.5
+            "
+          >
+            {groups.length > 0 ? groups : debouncedGroups}
+          </div>
+        </PopperUnstyled>
+      ) : null}
     </>
   );
 };
diff --git a/packages/core/src/widgets/markdown/plate/components/buttons/InsertImageToolbarButton.tsx b/packages/core/src/widgets/markdown/plate/components/buttons/InsertImageToolbarButton.tsx
index d116a474..dbf0f95a 100644
--- a/packages/core/src/widgets/markdown/plate/components/buttons/InsertImageToolbarButton.tsx
+++ b/packages/core/src/widgets/markdown/plate/components/buttons/InsertImageToolbarButton.tsx
@@ -1,6 +1,6 @@
 import { Image as ImageIcon } from '@styled-icons/material/Image';
-import { insertImage } from '@udecode/plate';
-import React, { useCallback, useMemo } from 'react';
+import { ELEMENT_IMAGE, getAboveNode, setNodes } from '@udecode/plate';
+import React, { useCallback, useMemo, useState } from 'react';
 
 import useMediaInsert from '@staticcms/core/lib/hooks/useMediaInsert';
 import { isNotEmpty } from '@staticcms/core/lib/util/string.util';
@@ -8,7 +8,9 @@ import { useMdPlateEditorState } from '@staticcms/markdown/plate/plateTypes';
 import ToolbarButton from './common/ToolbarButton';
 
 import type { Collection, MarkdownField, MediaPath } from '@staticcms/core/interface';
+import type { MdImageElement } from '@staticcms/markdown/plate/plateTypes';
 import type { FC } from 'react';
+import type { BaseSelection } from 'slate';
 
 export interface InsertImageToolbarButtonProps {
   variant: 'button' | 'menu';
@@ -25,14 +27,42 @@ const InsertImageToolbarButton: FC<InsertImageToolbarButtonProps> = ({
   currentValue,
   disabled,
 }) => {
+  const [selection, setSelection] = useState<BaseSelection>();
   const editor = useMdPlateEditorState();
   const handleInsert = useCallback(
     (newUrl: MediaPath<string>) => {
       if (isNotEmpty(newUrl.path)) {
-        insertImage(editor, newUrl.path);
+        const image: MdImageElement = {
+          type: ELEMENT_IMAGE,
+          url: newUrl.path,
+          children: [{ text: '' }],
+        };
+
+        const imageAbove = getAboveNode<MdImageElement>(editor, {
+          at: selection?.focus,
+          match: { type: ELEMENT_IMAGE },
+        });
+
+        if (imageAbove) {
+          if (newUrl.path !== imageAbove[0]?.url || newUrl.alt !== imageAbove[0]?.alt) {
+            setNodes<MdImageElement>(
+              editor,
+              { url: newUrl.path, alt: newUrl.alt },
+              {
+                at: imageAbove[1],
+              },
+            );
+          }
+
+          return;
+        }
+
+        setNodes<MdImageElement>(editor, image, {
+          at: selection?.focus,
+        });
       }
     },
-    [editor],
+    [editor, selection],
   );
 
   const chooseUrl = useMemo(() => field.choose_url ?? true, [field.choose_url]);
@@ -46,12 +76,17 @@ const InsertImageToolbarButton: FC<InsertImageToolbarButtonProps> = ({
     handleInsert,
   );
 
+  const handleOpenMediaLibrary = useCallback(() => {
+    setSelection(editor.selection);
+    openMediaLibrary();
+  }, [editor.selection, openMediaLibrary]);
+
   return (
     <ToolbarButton
       label="Image"
       tooltip="Insert image"
       icon={ImageIcon}
-      onClick={openMediaLibrary}
+      onClick={handleOpenMediaLibrary}
       disabled={disabled}
       variant={variant}
     />
diff --git a/packages/core/src/widgets/markdown/plate/components/buttons/InsertLinkToolbarButton.tsx b/packages/core/src/widgets/markdown/plate/components/buttons/InsertLinkToolbarButton.tsx
index 3138e777..269e1cb1 100644
--- a/packages/core/src/widgets/markdown/plate/components/buttons/InsertLinkToolbarButton.tsx
+++ b/packages/core/src/widgets/markdown/plate/components/buttons/InsertLinkToolbarButton.tsx
@@ -1,6 +1,15 @@
 import { Link as LinkIcon } from '@styled-icons/material/Link';
-import { ELEMENT_LINK, getSelectionText, insertLink, someNode } from '@udecode/plate';
-import React, { useCallback, useMemo } from 'react';
+import {
+  ELEMENT_LINK,
+  getEditorString,
+  getNode,
+  getSelectionText,
+  insertLink,
+  replaceNodeChildren,
+  setNodes,
+  someNode,
+} from '@udecode/plate';
+import React, { useCallback, useMemo, useState } from 'react';
 
 import useMediaInsert from '@staticcms/core/lib/hooks/useMediaInsert';
 import useUUID from '@staticcms/core/lib/hooks/useUUID';
@@ -9,7 +18,10 @@ import { useMdPlateEditorState } from '@staticcms/markdown/plate/plateTypes';
 import ToolbarButton from './common/ToolbarButton';
 
 import type { Collection, MarkdownField, MediaPath } from '@staticcms/core/interface';
+import type { MdLinkElement } from '@staticcms/markdown/plate/plateTypes';
+import type { TText } from '@udecode/plate';
 import type { FC } from 'react';
+import type { Path } from 'slate';
 
 export interface InsertLinkToolbarButtonProps {
   variant: 'button' | 'menu';
@@ -26,18 +38,49 @@ const InsertLinkToolbarButton: FC<InsertLinkToolbarButtonProps> = ({
   currentValue,
   disabled,
 }) => {
+  const [selection, setSelection] = useState<Path>();
   const editor = useMdPlateEditorState();
   const handleInsert = useCallback(
     ({ path: newUrl, alt: newText }: MediaPath<string>) => {
-      if (isNotEmpty(newUrl)) {
+      if (isNotEmpty(newUrl) && selection) {
+        const text = isNotEmpty(newText) ? newText : newUrl;
+        const linkAt = getNode<MdLinkElement>(editor, selection);
+
+        if (linkAt && linkAt.type === ELEMENT_LINK) {
+          if (newUrl !== linkAt.url || text !== linkAt.children[0].text) {
+            setNodes<MdLinkElement>(
+              editor,
+              { url: newUrl, children: [{ text: newText }] },
+              { at: selection },
+            );
+
+            if (text !== getEditorString(editor, selection)) {
+              replaceNodeChildren<TText>(editor, {
+                at: selection,
+                nodes: { text },
+                insertOptions: {
+                  select: true,
+                },
+              });
+            }
+          }
+
+          return;
+        }
+
         insertLink(
           editor,
-          { url: newUrl, text: isNotEmpty(newText) ? newText : newUrl },
-          { at: editor.selection ?? editor.prevSelection! },
+          { url: newUrl, text },
+          {
+            at: selection,
+          },
         );
+        const newSelection = [...selection];
+        const lastIndex = newSelection.pop() ?? 0;
+        setSelection([...newSelection, lastIndex + 1]);
       }
     },
-    [editor],
+    [editor, selection],
   );
 
   const chooseUrl = useMemo(() => field.choose_url ?? true, [field.choose_url]);
@@ -62,12 +105,17 @@ const InsertLinkToolbarButton: FC<InsertLinkToolbarButtonProps> = ({
     handleInsert,
   );
 
+  const handleOpenMediaLibrary = useCallback(() => {
+    setSelection(editor.selection?.focus.path);
+    openMediaLibrary();
+  }, [editor.selection, openMediaLibrary]);
+
   return (
     <ToolbarButton
       label="Link"
       tooltip="Insert link"
       icon={LinkIcon}
-      onClick={openMediaLibrary}
+      onClick={handleOpenMediaLibrary}
       active={isLink}
       disabled={disabled}
       variant={variant}
diff --git a/packages/core/src/widgets/markdown/plate/components/nodes/image/withImageElement.tsx b/packages/core/src/widgets/markdown/plate/components/nodes/image/withImageElement.tsx
index c6978c09..50c54a26 100644
--- a/packages/core/src/widgets/markdown/plate/components/nodes/image/withImageElement.tsx
+++ b/packages/core/src/widgets/markdown/plate/components/nodes/image/withImageElement.tsx
@@ -6,7 +6,7 @@ import {
   setSelection,
   usePlateSelection,
 } from '@udecode/plate';
-import React, { useCallback, useEffect, useRef, useState } from 'react';
+import React, { useCallback, useEffect, useMemo, useRef, useState } from 'react';
 import { useFocused } from 'slate-react';
 
 import useMediaAsset from '@staticcms/core/lib/hooks/useMediaAsset';
@@ -32,8 +32,7 @@ const withImageElement = ({ collection, entry, field }: WithImageElementProps) =
     editor,
     children,
   }) => {
-    const { url, alt } = element;
-    const [internalValue, setInternalValue] = useState<MediaPath<string>>({ path: url, alt });
+    const { url, alt } = useMemo(() => element, [element]);
     const [popoverHasFocus, setPopoverHasFocus] = useState(false);
     const debouncedPopoverHasFocus = useDebounce(popoverHasFocus, 100);
 
@@ -100,7 +99,6 @@ const withImageElement = ({ collection, entry, field }: WithImageElementProps) =
       (newValue: MediaPath<string>) => {
         handleChange(newValue.path, 'url');
         handleChange(newValue.alt ?? '', 'alt');
-        setInternalValue(newValue);
       },
       [handleChange],
     );
@@ -179,8 +177,8 @@ const withImageElement = ({ collection, entry, field }: WithImageElementProps) =
           anchorEl={anchorEl}
           collection={collection}
           field={field}
-          url={internalValue.path}
-          text={internalValue.alt}
+          url={url}
+          text={alt}
           onMediaChange={handleMediaChange}
           onRemove={handleRemove}
           forImage
diff --git a/packages/core/src/widgets/markdown/plate/components/nodes/link/withLinkElement.tsx b/packages/core/src/widgets/markdown/plate/components/nodes/link/withLinkElement.tsx
index 031856f1..5e906e53 100644
--- a/packages/core/src/widgets/markdown/plate/components/nodes/link/withLinkElement.tsx
+++ b/packages/core/src/widgets/markdown/plate/components/nodes/link/withLinkElement.tsx
@@ -8,7 +8,7 @@ import {
   unwrapLink,
   usePlateSelection,
 } from '@udecode/plate';
-import React, { useCallback, useEffect, useRef, useState } from 'react';
+import React, { useCallback, useEffect, useMemo, useRef, useState } from 'react';
 import { useFocused } from 'slate-react';
 
 import useDebounce from '@staticcms/core/lib/hooks/useDebounce';
@@ -34,13 +34,10 @@ const withLinkElement = ({ collection, field }: WithLinkElementProps) => {
   }) => {
     const urlRef = useRef<HTMLAnchorElement | null>(null);
 
-    const { url } = element;
     const path = findNodePath(editor, element);
 
-    const [internalValue, setInternalValue] = useState<MediaPath<string>>({
-      path: url,
-      alt: getEditorString(editor, path),
-    });
+    const { url } = useMemo(() => element, [element]);
+    const alt = useMemo(() => getEditorString(editor, path), [editor, path]);
     const [popoverHasFocus, setPopoverHasFocus] = useState(false);
     const debouncedPopoverHasFocus = useDebounce(popoverHasFocus, 100);
 
@@ -114,7 +111,6 @@ const withLinkElement = ({ collection, field }: WithLinkElementProps) => {
     const handleMediaChange = useCallback(
       (newValue: MediaPath<string>) => {
         handleChange(newValue.path, newValue.alt ?? '');
-        setInternalValue(newValue);
       },
       [handleChange],
     );
@@ -217,8 +213,8 @@ const withLinkElement = ({ collection, field }: WithLinkElementProps) => {
           anchorEl={anchorEl}
           collection={collection}
           field={field}
-          url={internalValue.path}
-          text={internalValue.alt}
+          url={url}
+          text={alt}
           onMediaChange={handleMediaChange}
           onRemove={handleRemove}
           onFocus={handlePopoverFocus}