diff --git a/src/components/layout/AppUploadAndPrintBtn.vue b/src/components/layout/AppUploadAndPrintBtn.vue
index 55d893f377..84ddb85b33 100644
--- a/src/components/layout/AppUploadAndPrintBtn.vue
+++ b/src/components/layout/AppUploadAndPrintBtn.vue
@@ -49,8 +49,11 @@ export default class AppUploadAndPrintBtn extends Vue {
   fileChanged (e: Event) {
     const target = e.target as HTMLInputElement
 
-    if (target?.files?.length === 1) {
-      this.$emit('upload', target.files[0])
+    if (target) {
+      if (target.files?.length === 1) {
+        this.$emit('upload', target.files[0])
+      }
+
       target.value = ''
     }
   }
diff --git a/src/components/widgets/filesystem/FileSystem.vue b/src/components/widgets/filesystem/FileSystem.vue
index 99514655a2..e55f3c6a39 100644
--- a/src/components/widgets/filesystem/FileSystem.vue
+++ b/src/components/widgets/filesystem/FileSystem.vue
@@ -156,6 +156,7 @@ import FileSystemUploadDialog from './FileSystemUploadDialog.vue'
 import FilePreviewDialog from './FilePreviewDialog.vue'
 import Axios from 'axios'
 import { AppTableHeader } from '@/types'
+import { FileWithPath, getFilesFromDataTransfer } from '@/util/file-system-entry'
 
 /**
  * Represents the filesystem, bound to moonrakers supplied roots.
@@ -821,7 +822,7 @@ export default class FileSystem extends Mixins(StateMixin, FilesMixin, ServicesM
     }
   }
 
-  async handleUpload (files: FileList | File[], print: boolean) {
+  async handleUpload (files: FileList | File[] | FileWithPath[], print: boolean) {
     this.$store.dispatch('wait/addWait', this.$waits.onFileSystem)
     this.uploadFiles(files, this.visiblePath, this.currentRoot, print)
     this.$store.dispatch('wait/removeWait', this.$waits.onFileSystem)
@@ -912,8 +913,15 @@ export default class FileSystem extends Mixins(StateMixin, FilesMixin, ServicesM
 
   async handleDropFile (e: DragEvent) {
     this.dragState.overlay = false
-    if (e && e.dataTransfer && e.dataTransfer.files.length && !this.rootProperties.readonly) {
-      this.handleUpload(e.dataTransfer.files, false)
+
+    if (!e.dataTransfer || this.rootProperties.readonly) {
+      return
+    }
+
+    const files = await getFilesFromDataTransfer(e.dataTransfer)
+
+    if (files) {
+      this.handleUpload(files, false)
     }
   }
 }
diff --git a/src/components/widgets/filesystem/FileSystemMenu.vue b/src/components/widgets/filesystem/FileSystemMenu.vue
index 56f5838686..7447aeec33 100644
--- a/src/components/widgets/filesystem/FileSystemMenu.vue
+++ b/src/components/widgets/filesystem/FileSystemMenu.vue
@@ -40,7 +40,22 @@
           >
             $fileUpload
           </v-icon>
-          {{ $t('app.general.btn.upload') }}
+          {{ $t('app.general.btn.upload_files') }}
+        </v-list-item-title>
+      </v-list-item>
+      <v-list-item
+        v-if="!readonly"
+        :disabled="disabled"
+        @click="emulateClick(false, true)"
+      >
+        <v-list-item-title>
+          <v-icon
+            small
+            left
+          >
+            $folderUpload
+          </v-icon>
+          {{ $t('app.general.btn.upload_folder') }}
         </v-list-item-title>
       </v-list-item>
       <v-list-item
@@ -101,6 +116,7 @@
 </template>
 
 <script lang="ts">
+import { getFilesWithPathFromHTMLInputElement } from '@/util/file-system-entry'
 import { Component, Vue, Prop, Ref } from 'vue-property-decorator'
 
 @Component({})
@@ -129,23 +145,23 @@ export default class FileSystemMenu extends Vue {
     return this.$store.getters['files/getRootProperties'](this.root).canCreateDirectory
   }
 
-  emulateClick (startPrint: boolean) {
+  emulateClick (startPrint: boolean, folder = false) {
     this.andPrint = startPrint
     this.uploadFile.multiple = !startPrint // Can't start print with multiple files
+    this.uploadFile.webkitdirectory = folder
     this.uploadFile.click()
   }
 
-  fileChanged (e: Event) {
+  async fileChanged (e: Event) {
     const target = e.target as HTMLInputElement
-    const files = target.files
-    const fileList = []
 
-    if (target && files && files.length > 0) {
-      for (let i = 0; i < files.length; i++) {
-        fileList.push(files[i])
+    if (target) {
+      const files = await getFilesWithPathFromHTMLInputElement(target)
+
+      if (files) {
+        this.$emit('upload', files, this.andPrint)
       }
 
-      this.$emit('upload', fileList, this.andPrint)
       target.value = ''
     }
   }
diff --git a/src/globals.ts b/src/globals.ts
index 6fc653c528..95f4b8c7b7 100644
--- a/src/globals.ts
+++ b/src/globals.ts
@@ -134,7 +134,8 @@ import {
   mdiArchive,
   mdiArchivePlus,
   mdiTrayFull,
-  mdiTrayPlus
+  mdiTrayPlus,
+  mdiFolderArrowUp
 } from '@mdi/js'
 
 /**
@@ -253,6 +254,7 @@ export const Icons = Object.freeze({
   alertCircle: mdiAlertCircle,
   folderAdd: mdiFolderPlus,
   folderUp: mdiFolderUpload,
+  folderUpload: mdiFolderArrowUp,
   folder: mdiFolder,
   fileUpload: mdiUpload,
   fileAdd: mdiFilePlus,
diff --git a/src/locales/en.yaml b/src/locales/en.yaml
index e30830311d..10ac1bacf7 100644
--- a/src/locales/en.yaml
+++ b/src/locales/en.yaml
@@ -196,6 +196,8 @@ app:
       socket_reconnect: Re-Connect
       socket_refresh: Force refresh
       upload: Upload
+      upload_files: Upload Files
+      upload_folder: Upload Folder
       upload_print: Upload & Print
       view: View
       reset_stats: Reset Stats
diff --git a/src/mixins/files.ts b/src/mixins/files.ts
index 3d383fd509..6650cd79ff 100644
--- a/src/mixins/files.ts
+++ b/src/mixins/files.ts
@@ -3,6 +3,7 @@ import Vue from 'vue'
 import { Component } from 'vue-property-decorator'
 import Axios, { AxiosRequestConfig, CancelTokenSource } from 'axios'
 import { httpClientActions } from '@/api/httpClientActions'
+import { FileWithPath } from '@/util/file-system-entry'
 
 @Component
 export default class FilesMixin extends Vue {
@@ -208,11 +209,12 @@ export default class FilesMixin extends Vue {
   async uploadFile (file: File, path: string, root: string, andPrint: boolean, options?: AxiosRequestConfig) {
     const formData = new FormData()
     // let filename = file.name.replace(' ', '_')
-    let filepath = `${path}/${file.name}`
+    let filepath = `${path}${file.name}`
     filepath = (filepath.startsWith('/'))
       ? filepath
       : '/' + filepath
-    formData.append('file', file, filepath)
+    formData.append('file', file, file.name)
+    formData.append('path', path)
     formData.append('root', root)
     if (andPrint) {
       formData.append('print', 'true')
@@ -266,17 +268,33 @@ export default class FilesMixin extends Vue {
       })
   }
 
+  getFullPathAndFile (rootPath: string, file: File | FileWithPath): [string, File] {
+    if ('path' in file) {
+      return [
+        `${rootPath}/${file.path}`,
+        file.file
+      ]
+    } else {
+      return [
+        rootPath,
+        file
+      ]
+    }
+  }
+
   // Upload some files.
-  async uploadFiles (files: FileList | File[], path: string, root: string, andPrint: boolean) {
+  async uploadFiles (files: FileList | File[] | FileWithPath[], path: string, root: string, andPrint: boolean) {
     // For each file, adds the associated state.
     for (const file of files) {
-      let filepath = `${path}/${file.name}`
+      const [fullPath, fileObject] = this.getFullPathAndFile(path, file)
+
+      let filepath = `${fullPath}${fileObject.name}`
       filepath = (filepath.startsWith('/'))
         ? filepath
         : '/' + filepath
       this.$store.dispatch('files/updateFileUpload', {
         filepath,
-        size: file.size,
+        size: fileObject.size,
         loaded: 0,
         percent: 0,
         speed: 0,
@@ -290,7 +308,9 @@ export default class FilesMixin extends Vue {
     // processing of each file.
     if (files.length > 1) andPrint = false
     for (const file of files) {
-      let filepath = `${path}/${file.name}`
+      const [fullPath, fileObject] = this.getFullPathAndFile(path, file)
+
+      let filepath = `${fullPath}${fileObject.name}`
       filepath = (filepath.startsWith('/'))
         ? filepath
         : '/' + filepath
@@ -299,7 +319,7 @@ export default class FilesMixin extends Vue {
       if (fileState && !fileState?.cancelled) {
         try {
           this.cancelTokenSource = Axios.CancelToken.source()
-          await this.uploadFile(file, path, root, andPrint, {
+          await this.uploadFile(fileObject, fullPath, root, andPrint, {
             cancelToken: this.cancelTokenSource.token
           })
         } catch (e) {
diff --git a/src/util/file-system-entry.ts b/src/util/file-system-entry.ts
new file mode 100644
index 0000000000..6373a95e0e
--- /dev/null
+++ b/src/util/file-system-entry.ts
@@ -0,0 +1,96 @@
+import consola from 'consola'
+
+type EntryWithPath = {
+  entry: FileSystemEntry,
+  path: string
+}
+export type FileWithPath = {
+  file: File,
+  path: string
+}
+
+const isFile = (item: FileSystemEntry): item is FileSystemFileEntry => item.isFile
+
+const isDirectory = (item: FileSystemEntry): item is FileSystemDirectoryEntry => item.isDirectory
+
+const getFileAsync = async (fileEntry: FileSystemFileEntry) => {
+  try {
+    return new Promise<File>((resolve, reject) => fileEntry.file(resolve, reject))
+  } catch (e) {
+    consola.error('[FileSystemFileEntry] file', e)
+  }
+}
+
+const readEntriesAsync = async (directoryReader: FileSystemDirectoryReader) => {
+  try {
+    return new Promise<FileSystemEntry[]>((resolve, reject) => directoryReader.readEntries(resolve, reject))
+  } catch (e) {
+    consola.error('[FileSystemDirectoryReader] readEntries', e)
+  }
+}
+
+export const getFilesFromDataTransfer = async (dataTransfer: DataTransfer) => {
+  if (dataTransfer.items.length) {
+    const entries = [...dataTransfer.items]
+      .map(x => x.webkitGetAsEntry())
+      .filter((x): x is FileSystemEntry => !!x)
+
+    return await getFilesFromFileSystemEntries(entries)
+  } else if (dataTransfer.files.length) {
+    return convertFilesToFilesWithPath(dataTransfer.files)
+  }
+}
+
+export const getFilesWithPathFromHTMLInputElement = async (input: HTMLInputElement) => {
+  if (input.webkitEntries.length) {
+    return await getFilesFromFileSystemEntries(input.webkitEntries)
+  } else if (input.files?.length) {
+    return convertFilesToFilesWithPath(input.files)
+  }
+}
+
+export const convertFilesToFilesWithPath = (files: File[] | FileList) => {
+  return [...files]
+    .map(file => ({
+      file,
+      path: file.webkitRelativePath.slice(0, -file.name.length)
+    } as FileWithPath))
+}
+
+export const getFilesFromFileSystemEntries = async (entries: readonly FileSystemEntry[]) => {
+  const files: FileWithPath[] = []
+  const items = entries
+    .map(entry => ({
+      entry,
+      path: ''
+    } as EntryWithPath))
+
+  let item = items.pop()
+  while (item) {
+    if (isFile(item.entry)) {
+      const file = await getFileAsync(item.entry)
+
+      if (file) {
+        files.push({
+          file,
+          path: item.path
+        })
+      }
+    } else if (isDirectory(item.entry)) {
+      const subEntries = await readEntriesAsync(item.entry.createReader())
+
+      if (subEntries) {
+        for (const entry of subEntries) {
+          items.push({
+            entry,
+            path: item.path + item.entry.name + '/'
+          })
+        }
+      }
+    }
+
+    item = items.pop()
+  }
+
+  return files
+}