diff --git a/src/cloud/components/ContentManager/index.tsx b/src/cloud/components/ContentManager/index.tsx
index 946e75a32c..30e8ffc6cb 100644
--- a/src/cloud/components/ContentManager/index.tsx
+++ b/src/cloud/components/ContentManager/index.tsx
@@ -42,6 +42,8 @@ const ContentManager = ({
   folders,
   workspacesMap,
   currentUserIsCoreMember,
+  currentWorkspaceId,
+  currentFolderId,
   page,
 }: ContentManagerProps) => {
   const { preferences, setPreferences } = usePreferences()
@@ -118,8 +120,12 @@ const ContentManager = ({
     [setPreferences]
   )
 
-  const { dropInDocOrFolder, saveDocTransferData, clearDragTransferData } =
-    useCloudDnd()
+  const {
+    dropFilesAsDocs,
+    dropInDocOrFolder,
+    saveDocTransferData,
+    clearDragTransferData,
+  } = useCloudDnd()
 
   const onDragStartDoc = useCallback(
     (event: any, doc: SerializedDocWithSupplemental) => {
@@ -145,8 +151,28 @@ const ContentManager = ({
     [clearDragTransferData]
   )
 
+  const onDragOverFiles = useCallback((event: React.DragEvent) => {
+    if (event.dataTransfer.types.includes('Files')) {
+      event.preventDefault()
+    }
+  }, [])
+
+  const onDropFiles = useCallback(
+    (event: React.DragEvent) => {
+      if (currentWorkspaceId == null) {
+        return
+      }
+
+      dropFilesAsDocs(event, team, {
+        workspaceId: currentWorkspaceId,
+        parentFolderId: currentFolderId,
+      })
+    },
+    [currentFolderId, currentWorkspaceId, dropFilesAsDocs, team]
+  )
+
   return (
-    <Container>
+    <Container onDragOver={onDragOverFiles} onDrop={onDropFiles}>
       <Scroller className='cm__scroller'>
         <StyledContentManagerHeader>
           <div className='header__left' />
diff --git a/src/cloud/lib/hooks/sidebar/useCloudDnd.ts b/src/cloud/lib/hooks/sidebar/useCloudDnd.ts
index 292b694103..75dc0d9380 100644
--- a/src/cloud/lib/hooks/sidebar/useCloudDnd.ts
+++ b/src/cloud/lib/hooks/sidebar/useCloudDnd.ts
@@ -1,5 +1,9 @@
 import { useCallback } from 'react'
-import { UpdateDocRequestBody } from '../../../api/teams/docs'
+import {
+  createDoc,
+  CreateDocRequestBody,
+  UpdateDocRequestBody,
+} from '../../../api/teams/docs'
 import { UpdateFolderRequestBody } from '../../../api/teams/folders'
 import { moveResource } from '../../../api/teams/resources'
 import {
@@ -20,23 +24,107 @@ import {
 } from '../../utils/patterns'
 import { SerializedFolderWithBookmark } from '../../../interfaces/db/folder'
 import { SerializedDocWithSupplemental } from '../../../interfaces/db/doc'
+import { SerializedTeam } from '../../../interfaces/db/team'
 import { SidebarDragState } from '../../../../design/lib/dnd'
 import { useToast } from '../../../../design/lib/stores/toast'
 import { getMapFromEntityArray } from '../../../../design/lib/utils/array'
 
+const textFileExtensions = new Set(['.md', '.txt', '.html', '.htm'])
+
+function getDroppedFiles(event: any) {
+  return Array.from<File>(event.dataTransfer?.files || []).filter((file) => {
+    const lowerCaseName = file.name.toLowerCase()
+    return Array.from(textFileExtensions).some((extension) =>
+      lowerCaseName.endsWith(extension)
+    )
+  })
+}
+
+function getDocTitleFromFileName(fileName: string) {
+  const matchingExtension = Array.from(textFileExtensions).find((extension) =>
+    fileName.toLowerCase().endsWith(extension)
+  )
+
+  if (matchingExtension == null) {
+    return fileName
+  }
+
+  return fileName.slice(0, -matchingExtension.length) || fileName
+}
+
+function readTextFile(file: File) {
+  return new Promise<string>((resolve, reject) => {
+    const reader = new FileReader()
+    reader.onload = () => resolve(String(reader.result || ''))
+    reader.onerror = () => reject(reader.error)
+    reader.readAsText(file)
+  })
+}
+
 export function useCloudDnd() {
   const {
     updateFoldersMap,
     updateDocsMap,
     updateWorkspacesMap,
+    updateParentFolderOfDoc,
+    updateParentWorkspaceOfDoc,
     setCurrentPath,
   } = useNav()
   const { pageDoc, pageFolder } = usePage()
   const { pushApiErrorMessage } = useToast()
 
+  const dropFilesAsDocs = useCallback(
+    async (
+      event: any,
+      team: SerializedTeam,
+      destination: Pick<CreateDocRequestBody, 'workspaceId' | 'parentFolderId'>
+    ) => {
+      const files = getDroppedFiles(event)
+      if (files.length === 0) {
+        return false
+      }
+
+      event.preventDefault()
+      event.stopPropagation()
+
+      try {
+        for (const file of files) {
+          const content = await readTextFile(file)
+          const { doc } = await createDoc(
+            { id: team.id },
+            {
+              ...destination,
+              title: getDocTitleFromFileName(file.name),
+              content,
+            }
+          )
+
+          updateDocsMap([doc.id, doc])
+
+          if (doc.parentFolder != null) {
+            updateParentFolderOfDoc(doc)
+          } else if (doc.workspace != null) {
+            updateParentWorkspaceOfDoc(doc)
+          }
+        }
+      } catch (error) {
+        pushApiErrorMessage(error)
+      }
+
+      return true
+    },
+    [
+      pushApiErrorMessage,
+      updateDocsMap,
+      updateParentFolderOfDoc,
+      updateParentWorkspaceOfDoc,
+    ]
+  )
+
   const dropInWorkspace = useCallback(
     async (
       event: any,
+      team: SerializedTeam,
       workspaceId: string,
       updateFolder: (
         folder: FolderDataTransferItem,
@@ -47,6 +135,11 @@ export function useCloudDnd() {
         body: UpdateDocRequestBody
       ) => Promise<void>
     ) => {
+      const droppedFiles = await dropFilesAsDocs(event, team, { workspaceId })
+      if (droppedFiles) {
+        return
+      }
+
       const draggedResource = getDraggedResource(event)
       if (draggedResource === null) {
         return
@@ -69,7 +162,7 @@ export function useCloudDnd() {
         })
       }
     },
-    []
+    [dropFilesAsDocs]
   )
 
   const dropInDocOrFolder = useCallback(
@@ -171,6 +264,7 @@ export function useCloudDnd() {
   }, [])
 
   return {
+    dropFilesAsDocs,
     dropInWorkspace,
     dropInDocOrFolder,
     saveFolderTransferData,
diff --git a/src/cloud/lib/hooks/sidebar/useCloudSidebarTree.tsx b/src/cloud/lib/hooks/sidebar/useCloudSidebarTree.tsx
index aaee5fd9e3..7be81c5caa 100644
--- a/src/cloud/lib/hooks/sidebar/useCloudSidebarTree.tsx
+++ b/src/cloud/lib/hooks/sidebar/useCloudSidebarTree.tsx
@@ -109,6 +109,7 @@ export function useCloudSidebarTree() {
   } = useSidebarCollapse()
 
   const {
+    dropFilesAsDocs,
     dropInDocOrFolder,
     dropInWorkspace,
     saveFolderTransferData,
@@ -263,7 +264,7 @@ export function useCloudSidebarTree() {
           ? {
               dropIn: true,
               onDrop: (event: any) =>
-                dropInWorkspace(event, wp.id, updateFolder, updateDoc),
+                dropInWorkspace(event, team, wp.id, updateFolder, updateDoc),
               controls: [
                 {
                   icon: mdiTextBoxPlus,
@@ -339,15 +340,24 @@ export function useCloudSidebarTree() {
       const coreRestrictedFeatures: Partial<CloudTreeItem> =
         currentUserIsCoreMember
           ? {
-              onDrop: (event: any, position: SidebarDragState) =>
-                dropInDocOrFolder(
+              onDrop: async (event: any, position: SidebarDragState) => {
+                const droppedFiles = await dropFilesAsDocs(event, team, {
+                  parentFolderId: folder.id,
+                  workspaceId: folder.workspaceId,
+                })
+                if (droppedFiles) {
+                  return
+                }
+
+                return dropInDocOrFolder(
                   event,
                   {
                     type: 'folder',
                     resource: folderToDataTransferItem(folder),
                   },
                   position
-                ),
+                )
+              },
               onDragStart: (event: any) => {
                 saveFolderTransferData(event, folder)
               },
@@ -941,6 +951,7 @@ export function useCloudSidebarTree() {
     treeSendingMap,
     sideBarOpenedFolderIdsSet,
     dropInDocOrFolder,
+    dropFilesAsDocs,
     saveFolderTransferData,
     clearDragTransferData,
     toggleFolderBookmark,