diff --git a/app/browser/reducers/sitesReducer.js b/app/browser/reducers/sitesReducer.js
index fefb6768717..17dde85f0fb 100644
--- a/app/browser/reducers/sitesReducer.js
+++ b/app/browser/reducers/sitesReducer.js
@@ -96,7 +96,7 @@ const sitesReducer = (state, action, immutableAction) => {
 
         if (closestKey != null) {
           const sourceKey = siteUtil.getSiteKey(site)
-          state = siteUtil.moveSite(state, sourceKey, closestKey, false, false, true)
+          state = siteUtil.moveSite(state, sourceKey, closestKey, !!action.isLeftSide, false, true)
         }
 
         if (isSyncEnabled) {
diff --git a/app/renderer/components/bookmarks/bookmarksToolbar.js b/app/renderer/components/bookmarks/bookmarksToolbar.js
index 5ec443ffa8a..485a668282c 100644
--- a/app/renderer/components/bookmarks/bookmarksToolbar.js
+++ b/app/renderer/components/bookmarks/bookmarksToolbar.js
@@ -48,15 +48,18 @@ class BookmarksToolbar extends React.Component {
 
   onDrop (e) {
     e.preventDefault()
-    const bookmark = dnd.prepareBookmarkDataFromCompatible(e.dataTransfer)
-    if (bookmark) {
-      // Figure out the droppedOn element filtering out the source drag item
-      let droppedOn = dnd.closestFromXOffset(this.bookmarkRefs.filter((bookmarkRef) => {
+    const getClosestFromPos = (clientX, sourceKey) =>
+      dnd.closestFromXOffset(this.bookmarkRefs.filter((bookmarkRef) => {
         if (!bookmarkRef) {
           return false
         }
-        return bookmarkRef.props.bookmarkKey !== bookmark.get('bookmarkKey')
+        return bookmarkRef.props.bookmarkKey !== sourceKey
       }), e.clientX)
+    const bookmark = dnd.prepareBookmarkDataFromCompatible(e.dataTransfer)
+    if (bookmark) {
+      // Figure out the droppedOn element filtering out the source drag item
+      const bookmarkKey = bookmark.get('bookmarkKey')
+      const droppedOn = getClosestFromPos(e.clientX, bookmarkKey)
       if (droppedOn.selectedRef) {
         const isLeftSide = dnd.isLeftSide(ReactDOM.findDOMNode(droppedOn.selectedRef), e.clientX)
         const droppedOnKey = droppedOn.selectedRef.props.bookmarkKey
@@ -66,6 +69,15 @@ class BookmarksToolbar extends React.Component {
       }
       return
     }
+
+    const droppedOn = getClosestFromPos(e.clientX, undefined)
+    let isLeftSide = false
+    let closestKey
+    if (droppedOn.selectedRef) {
+      closestKey = droppedOn.selectedRef.props.bookmarkKey
+      isLeftSide = dnd.isLeftSide(ReactDOM.findDOMNode(droppedOn.selectedRef), e.clientX)
+    }
+
     const droppedHTML = e.dataTransfer.getData('text/html')
     if (droppedHTML) {
       const parser = new window.DOMParser()
@@ -75,14 +87,14 @@ class BookmarksToolbar extends React.Component {
         appActions.addBookmark({
           title: a.innerText,
           location: e.dataTransfer.getData('text/plain')
-        }, siteTags.BOOKMARK)
+        }, siteTags.BOOKMARK, closestKey, isLeftSide)
         return
       }
     }
 
     if (e.dataTransfer.files.length > 0) {
       Array.from(e.dataTransfer.items).forEach((item) => {
-        item.getAsString((name) => appActions.addBookmark({ location: item.type, title: name }, siteTags.BOOKMARK))
+        item.getAsString((name) => appActions.addBookmark({ location: item.type, title: name }, siteTags.BOOKMARK, closestKey, isLeftSide))
       })
       return
     }
@@ -92,7 +104,7 @@ class BookmarksToolbar extends React.Component {
       .map((x) => x.trim())
       .filter((x) => !x.startsWith('#') && x.length > 0)
       .forEach((url) =>
-        appActions.addBookmark({ location: url }, siteTags.BOOKMARK))
+        appActions.addBookmark({ location: url }, siteTags.BOOKMARK, closestKey, isLeftSide))
   }
 
   onDragEnter (e) {
diff --git a/js/actions/appActions.js b/js/actions/appActions.js
index a1cc4660b4c..130820c22e2 100644
--- a/js/actions/appActions.js
+++ b/js/actions/appActions.js
@@ -1517,12 +1517,13 @@ const appActions = {
     })
   },
 
-  addBookmark: function (siteDetail, tag, closestKey) {
+  addBookmark: function (siteDetail, tag, closestKey, isLeftSide = false) {
     dispatch({
       actionType: appConstants.APP_ADD_BOOKMARK,
       siteDetail,
       tag,
-      closestKey
+      closestKey,
+      isLeftSide
     })
   },
 
diff --git a/test/unit/app/browser/reducers/sitesReducerTest.js b/test/unit/app/browser/reducers/sitesReducerTest.js
index c63d752b73c..6a63a2b1336 100644
--- a/test/unit/app/browser/reducers/sitesReducerTest.js
+++ b/test/unit/app/browser/reducers/sitesReducerTest.js
@@ -332,6 +332,92 @@ describe('sitesReducerTest', function () {
       const result = sitesReducer(state, action)
       assert.deepEqual(result.get('sites').toJS(), newSites)
     })
+
+    it('add a bookmark with a close bookmark prepending', function () {
+      const state = initState.set('sites', makeImmutable({
+        'https://www.clifton.io|0|0': {
+          lastAccessedTime: 0,
+          tags: [siteTags.BOOKMARK],
+          objectId: undefined,
+          title: 'Brave',
+          order: 0,
+          location: 'https://www.brave.com',
+          parentFolderId: 0
+        },
+        'https://www.bbondy.io|0|0': {
+          lastAccessedTime: 0,
+          tags: [siteTags.BOOKMARK],
+          objectId: undefined,
+          title: 'Brave',
+          order: 1,
+          location: 'https://www.bbondy.io',
+          parentFolderId: 0
+        },
+        'https://www.bridiver.io|0|0': {
+          lastAccessedTime: 0,
+          tags: [siteTags.BOOKMARK],
+          objectId: undefined,
+          title: 'Brave',
+          order: 2,
+          location: 'https://www.bridiver.io',
+          parentFolderId: 0
+        }
+      }))
+
+      const action = {
+        actionType: appConstants.APP_ADD_BOOKMARK,
+        siteDetail: makeImmutable({
+          parentFolderId: 0,
+          title: 'Brave',
+          location: 'https://www.brave.com'
+        }),
+        tag: siteTags.BOOKMARK,
+        closestKey: 'https://www.bbondy.io|0|0',
+        isLeftSide: true
+      }
+
+      const newSites = {
+        'https://www.clifton.io|0|0': {
+          lastAccessedTime: 0,
+          tags: [siteTags.BOOKMARK],
+          objectId: undefined,
+          title: 'Brave',
+          order: 0,
+          location: 'https://www.brave.com',
+          parentFolderId: 0
+        },
+        'https://www.bbondy.io|0|0': {
+          lastAccessedTime: 0,
+          tags: [siteTags.BOOKMARK],
+          objectId: undefined,
+          title: 'Brave',
+          order: 2,
+          location: 'https://www.bbondy.io',
+          parentFolderId: 0
+        },
+        'https://www.brave.com|0|0': {
+          lastAccessedTime: 0,
+          tags: [siteTags.BOOKMARK],
+          objectId: undefined,
+          title: 'Brave',
+          order: 1,
+          location: 'https://www.brave.com',
+          parentFolderId: 0
+        },
+        'https://www.bridiver.io|0|0': {
+          lastAccessedTime: 0,
+          tags: [siteTags.BOOKMARK],
+          objectId: undefined,
+          title: 'Brave',
+          order: 3,
+          location: 'https://www.bridiver.io',
+          parentFolderId: 0
+        }
+      }
+
+      const result = sitesReducer(state, action)
+      assert.deepEqual(result.get('sites').toJS(), newSites)
+    })
   })
 
   describe('APP_EDIT_BOOKMARK', function () {