diff --git a/client/components/tables/LibraryFilesTable.vue b/client/components/tables/LibraryFilesTable.vue
index d941e6085..b73c96b04 100644
--- a/client/components/tables/LibraryFilesTable.vue
+++ b/client/components/tables/LibraryFilesTable.vue
@@ -18,25 +18,10 @@
             <th class="text-left px-4">{{ $strings.LabelPath }}</th>
             <th class="text-left w-24 min-w-24">{{ $strings.LabelSize }}</th>
             <th class="text-left px-4 w-24">{{ $strings.LabelType }}</th>
-            <th v-if="userCanDownload && !isMissing" class="text-center w-20">{{ $strings.LabelDownload }}</th>
+            <th v-if="userCanDelete || userCanDownload" class="text-center w-16"></th>
           </tr>
           <template v-for="file in files">
-            <tr :key="file.path">
-              <td class="px-4">
-                {{ showFullPath ? file.metadata.path : file.metadata.relPath }}
-              </td>
-              <td class="font-mono">
-                {{ $bytesPretty(file.metadata.size) }}
-              </td>
-              <td class="text-xs">
-                <div class="flex items-center">
-                  <p>{{ file.fileType }}</p>
-                </div>
-              </td>
-              <td v-if="userCanDownload && !isMissing" class="text-center">
-                <a :href="`${$config.routerBasePath}/s/item/${libraryItemId}/${$encodeUriPath(file.metadata.relPath).replace(/^\//, '')}?token=${userToken}`" download><span class="material-icons icon-text">download</span></a>
-              </td>
-            </tr>
+            <tables-library-files-table-row :key="file.path" :libraryItemId="libraryItemId" :showFullPath="showFullPath" :file="file" />
           </template>
         </table>
       </div>
@@ -68,6 +53,9 @@ export default {
     userCanDownload() {
       return this.$store.getters['user/getUserCanDownload']
     },
+    userCanDelete() {
+      return this.$store.getters['user/getUserCanDelete']
+    },
     userIsAdmin() {
       return this.$store.getters['user/getIsAdminOrUp']
     }
diff --git a/client/components/tables/LibraryFilesTableRow.vue b/client/components/tables/LibraryFilesTableRow.vue
new file mode 100644
index 000000000..b104b968a
--- /dev/null
+++ b/client/components/tables/LibraryFilesTableRow.vue
@@ -0,0 +1,105 @@
+<template>
+  <tr>
+    <td class="px-4">
+      {{ showFullPath ? file.metadata.path : file.metadata.relPath }}
+    </td>
+    <td class="font-mono">
+      {{ $bytesPretty(file.metadata.size) }}
+    </td>
+    <td class="text-xs">
+      <div class="flex items-center">
+        <p>{{ file.fileType }}</p>
+      </div>
+    </td>
+    <td v-if="contextMenuItems.length" class="text-center">
+      <ui-context-menu-dropdown :items="contextMenuItems" menu-width="110px" @action="contextMenuAction" />
+    </td>
+  </tr>
+</template>
+
+<script>
+export default {
+  props: {
+    libraryItemId: String,
+    showFullPath: Boolean,
+    file: {
+      type: Object,
+      default: () => {}
+    }
+  },
+  data() {
+    return {}
+  },
+  computed: {
+    userToken() {
+      return this.$store.getters['user/getToken']
+    },
+    userCanDownload() {
+      return this.$store.getters['user/getUserCanDownload']
+    },
+    userCanDelete() {
+      return this.$store.getters['user/getUserCanDelete']
+    },
+    downloadUrl() {
+      return `${process.env.serverUrl}/s/item/${this.libraryItemId}/${this.$encodeUriPath(this.file.metadata.relPath).replace(/^\//, '')}?token=${this.userToken}`
+    },
+    contextMenuItems() {
+      const items = []
+      if (this.userCanDownload) {
+        items.push({
+          text: this.$strings.LabelDownload,
+          action: 'download'
+        })
+      }
+      if (this.userCanDelete) {
+        items.push({
+          text: this.$strings.ButtonDelete,
+          action: 'delete'
+        })
+      }
+      return items
+    }
+  },
+  methods: {
+    contextMenuAction(action) {
+      if (action === 'delete') {
+        this.deleteLibraryFile()
+      } else if (action === 'download') {
+        this.downloadLibraryFile()
+      }
+    },
+    deleteLibraryFile() {
+      const payload = {
+        message: 'This will delete the file from your file system. Are you sure?',
+        callback: (confirmed) => {
+          if (confirmed) {
+            this.$axios
+              .$delete(`/api/items/${this.libraryItemId}/file/${this.file.ino}`)
+              .then(() => {
+                this.$toast.success('File deleted')
+              })
+              .catch((error) => {
+                console.error('Failed to delete file', error)
+                this.$toast.error('Failed to delete file')
+              })
+          }
+        },
+        type: 'yesNo'
+      }
+      this.$store.commit('globals/setConfirmPrompt', payload)
+    },
+    downloadLibraryFile() {
+      const a = document.createElement('a')
+      a.style.display = 'none'
+      a.href = this.downloadUrl
+      a.download = this.file.metadata.filename
+      document.body.appendChild(a)
+      a.click()
+      setTimeout(() => {
+        a.remove()
+      })
+    }
+  },
+  mounted() {}
+}
+</script>
\ No newline at end of file
diff --git a/client/components/ui/ContextMenuDropdown.vue b/client/components/ui/ContextMenuDropdown.vue
index 018bf34b8..6f486d5d6 100644
--- a/client/components/ui/ContextMenuDropdown.vue
+++ b/client/components/ui/ContextMenuDropdown.vue
@@ -1,11 +1,13 @@
 <template>
   <div class="relative h-9 w-9" v-click-outside="clickOutsideObj">
-    <button type="button" :disabled="disabled" class="relative h-full w-full flex items-center justify-center shadow-sm pl-3 pr-3 text-left focus:outline-none cursor-pointer text-gray-100 hover:text-gray-200 rounded-full hover:bg-white/5" aria-haspopup="listbox" :aria-expanded="showMenu" @click.stop.prevent="clickShowMenu">
-      <span class="material-icons" :class="iconClass">more_vert</span>
-    </button>
+    <slot :disabled="disabled" :showMenu="showMenu" :clickShowMenu="clickShowMenu">
+      <button type="button" :disabled="disabled" class="relative h-full w-full flex items-center justify-center shadow-sm pl-3 pr-3 text-left focus:outline-none cursor-pointer text-gray-100 hover:text-gray-200 rounded-full hover:bg-white/5" aria-haspopup="listbox" :aria-expanded="showMenu" @click.stop.prevent="clickShowMenu">
+        <span class="material-icons" :class="iconClass">more_vert</span>
+      </button>
+    </slot>
 
     <transition name="menu">
-      <div v-show="showMenu" class="absolute right-0 mt-1 z-10 bg-bg border border-black-200 shadow-lg max-h-56 w-48 rounded-md py-1 overflow-auto focus:outline-none sm:text-sm">
+      <div v-show="showMenu" class="absolute right-0 mt-1 z-10 bg-bg border border-black-200 shadow-lg max-h-56 rounded-md py-1 overflow-auto focus:outline-none sm:text-sm" :style="{ width: menuWidth }">
         <template v-for="(item, index) in items">
           <div :key="index" class="flex items-center px-2 py-1.5 hover:bg-white hover:bg-opacity-5 text-white text-xs cursor-pointer" @click.stop="clickAction(item.action)">
             <p>{{ item.text }}</p>
@@ -27,6 +29,10 @@ export default {
     iconClass: {
       type: String,
       default: ''
+    },
+    menuWidth: {
+      type: String,
+      default: '192px'
     }
   },
   data() {
diff --git a/client/pages/item/_id/index.vue b/client/pages/item/_id/index.vue
index dce627899..2d3766468 100644
--- a/client/pages/item/_id/index.vue
+++ b/client/pages/item/_id/index.vue
@@ -201,34 +201,18 @@
               <ui-read-icon-btn :disabled="isProcessingReadUpdate" :is-read="userIsFinished" class="mx-0.5" @click="toggleFinished" />
             </ui-tooltip>
 
-            <ui-tooltip v-if="showCollectionsButton" :text="$strings.LabelCollections" direction="top">
-              <ui-icon-btn icon="collections_bookmark" class="mx-0.5" outlined @click="collectionsClick" />
-            </ui-tooltip>
-
-            <ui-tooltip v-if="!isPodcast && tracks.length" :text="$strings.LabelYourPlaylists" direction="top">
-              <ui-icon-btn icon="playlist_add" class="mx-0.5" outlined @click="playlistsClick" />
-            </ui-tooltip>
-
             <!-- Only admin or root user can download new episodes -->
             <ui-tooltip v-if="isPodcast && userIsAdminOrUp" :text="$strings.LabelFindEpisodes" direction="top">
               <ui-icon-btn icon="search" class="mx-0.5" :loading="fetchingRSSFeed" outlined @click="findEpisodesClick" />
             </ui-tooltip>
 
-            <ui-tooltip v-if="bookmarks.length" :text="$strings.LabelYourBookmarks" direction="top">
-              <ui-icon-btn :icon="bookmarks.length ? 'bookmarks' : 'bookmark_border'" class="mx-0.5" @click="clickBookmarksBtn" />
-            </ui-tooltip>
-
-            <!-- RSS feed -->
-            <ui-tooltip v-if="showRssFeedBtn" :text="$strings.LabelOpenRSSFeed" direction="top">
-              <ui-icon-btn icon="rss_feed" class="mx-0.5" :bg-color="rssFeed ? 'success' : 'primary'" outlined @click="clickRSSFeed" />
-            </ui-tooltip>
-
-            <!-- Download -->
-            <ui-tooltip v-if="userCanDownload" :text="$strings.LabelDownload" direction="top">
-              <a :href="downloadPath" class="h-9 w-9 mx-0.5 rounded-md flex items-center justify-center relative bg-primary border border-gray-600">
-                <span class="material-icons-outlined" :style="{ fontSize: '1.4rem' }">download</span>
-              </a>
-            </ui-tooltip>
+            <ui-context-menu-dropdown v-if="contextMenuItems.length" :items="contextMenuItems" menu-width="148px" @action="contextMenuAction">
+              <template #default="{ showMenu, clickShowMenu, disabled }">
+                <button type="button" :disabled="disabled" class="mx-0.5 icon-btn bg-primary border border-gray-600 w-9 h-9 rounded-md flex items-center justify-center relative" aria-haspopup="listbox" :aria-expanded="showMenu" @click.stop.prevent="clickShowMenu">
+                  <span class="material-icons">more_vert</span>
+                </button>
+              </template>
+            </ui-context-menu-dropdown>
           </div>
 
           <div class="my-4 max-w-2xl">
@@ -294,7 +278,7 @@ export default {
     userToken() {
       return this.$store.getters['user/getToken']
     },
-    downloadPath() {
+    downloadUrl() {
       return `${process.env.serverUrl}/api/items/${this.libraryItemId}/download?token=${this.userToken}`
     },
     dateFormat() {
@@ -309,9 +293,6 @@ export default {
     userIsAdminOrUp() {
       return this.$store.getters['user/getIsAdminOrUp']
     },
-    isFile() {
-      return this.libraryItem.isFile
-    },
     bookCoverAspectRatio() {
       return this.$store.getters['libraries/getBookCoverAspectRatio']
     },
@@ -321,6 +302,9 @@ export default {
     isDeveloperMode() {
       return this.$store.state.developerMode
     },
+    isFile() {
+      return this.libraryItem.isFile
+    },
     isBook() {
       return this.libraryItem.mediaType === 'book'
     },
@@ -539,12 +523,56 @@ export default {
     },
     showCollectionsButton() {
       return this.isBook && this.userCanUpdate
+    },
+    contextMenuItems() {
+      const items = []
+
+      if (this.showCollectionsButton) {
+        items.push({
+          text: this.$strings.LabelCollections,
+          action: 'collections'
+        })
+      }
+
+      if (!this.isPodcast && this.tracks.length) {
+        items.push({
+          text: this.$strings.LabelYourPlaylists,
+          action: 'playlists'
+        })
+      }
+
+      if (this.bookmarks.length) {
+        items.push({
+          text: this.$strings.LabelYourBookmarks,
+          action: 'bookmarks'
+        })
+      }
+
+      if (this.showRssFeedBtn) {
+        items.push({
+          text: this.$strings.LabelOpenRSSFeed,
+          action: 'rss-feeds'
+        })
+      }
+
+      if (this.userCanDownload) {
+        items.push({
+          text: this.$strings.LabelDownload,
+          action: 'download'
+        })
+      }
+
+      // if (this.userCanDelete) {
+      //   items.push({
+      //     text: this.$strings.ButtonDelete,
+      //     action: 'delete'
+      //   })
+      // }
+
+      return items
     }
   },
   methods: {
-    clickBookmarksBtn() {
-      this.showBookmarksModal = true
-    },
     selectBookmark(bookmark) {
       if (!bookmark) return
       if (this.isStreaming) {
@@ -720,14 +748,6 @@ export default {
           })
       }
     },
-    collectionsClick() {
-      this.$store.commit('setSelectedLibraryItem', this.libraryItem)
-      this.$store.commit('globals/setShowCollectionsModal', true)
-    },
-    playlistsClick() {
-      this.$store.commit('globals/setSelectedPlaylistItems', [{ libraryItem: this.libraryItem }])
-      this.$store.commit('globals/setShowPlaylistsModal', true)
-    },
     clickRSSFeed() {
       this.$store.commit('globals/setRSSFeedOpenCloseModal', {
         id: this.libraryItemId,
@@ -785,6 +805,54 @@ export default {
         }
         this.$store.commit('addItemToQueue', queueItem)
       }
+    },
+    downloadLibraryItem() {
+      const a = document.createElement('a')
+      a.style.display = 'none'
+      a.href = this.downloadUrl
+      document.body.appendChild(a)
+      a.click()
+      setTimeout(() => {
+        a.remove()
+      })
+    },
+    deleteLibraryItem() {
+      const payload = {
+        message: 'This will delete the library item files from your file system. Are you sure?',
+        callback: (confirmed) => {
+          if (confirmed) {
+            this.$axios
+              .$delete(`/api/items/${this.libraryItemId}?hard=1`)
+              .then(() => {
+                this.$toast.success('Item deleted')
+                this.$router.replace(`/library/${this.libraryId}/bookshelf`)
+              })
+              .catch((error) => {
+                console.error('Failed to delete item', error)
+                this.$toast.error('Failed to delete item')
+              })
+          }
+        },
+        type: 'yesNo'
+      }
+      this.$store.commit('globals/setConfirmPrompt', payload)
+    },
+    contextMenuAction(action) {
+      if (action === 'collections') {
+        this.$store.commit('setSelectedLibraryItem', this.libraryItem)
+        this.$store.commit('globals/setShowCollectionsModal', true)
+      } else if (action === 'playlists') {
+        this.$store.commit('globals/setSelectedPlaylistItems', [{ libraryItem: this.libraryItem }])
+        this.$store.commit('globals/setShowPlaylistsModal', true)
+      } else if (action === 'bookmarks') {
+        this.showBookmarksModal = true
+      } else if (action === 'rss-feeds') {
+        this.clickRSSFeed()
+      } else if (action === 'download') {
+        this.downloadLibraryItem()
+      } else if (action === 'delete') {
+        this.deleteLibraryItem()
+      }
     }
   },
   mounted() {
diff --git a/server/controllers/LibraryItemController.js b/server/controllers/LibraryItemController.js
index b1b8cc6ad..842db1777 100644
--- a/server/controllers/LibraryItemController.js
+++ b/server/controllers/LibraryItemController.js
@@ -482,6 +482,28 @@ class LibraryItemController {
     res.json(toneData)
   }
 
+  async deleteLibraryFile(req, res) {
+    const libraryFile = req.libraryItem.libraryFiles.find(lf => lf.ino === req.params.ino)
+    if (!libraryFile) {
+      Logger.error(`[LibraryItemController] Unable to delete library file. Not found. "${req.params.ino}"`)
+      return res.sendStatus(404)
+    }
+
+    await fs.remove(libraryFile.metadata.path)
+    req.libraryItem.removeLibraryFile(req.params.ino)
+
+    if (req.libraryItem.media.removeFileWithInode(req.params.ino)) {
+      // If book has no more media files then mark it as missing
+      if (req.libraryItem.mediaType === 'book' && !req.libraryItem.media.hasMediaEntities) {
+        req.libraryItem.setMissing()
+      }
+    }
+    req.libraryItem.updatedAt = Date.now()
+    await this.db.updateLibraryItem(req.libraryItem)
+    SocketAuthority.emitter('item_updated', req.libraryItem.toJSONExpanded())
+    res.sendStatus(200)
+  }
+
   middleware(req, res, next) {
     const item = this.db.libraryItems.find(li => li.id === req.params.id)
     if (!item || !item.media) return res.sendStatus(404)
diff --git a/server/objects/mediaTypes/Podcast.js b/server/objects/mediaTypes/Podcast.js
index efce8bb28..46c34a394 100644
--- a/server/objects/mediaTypes/Podcast.js
+++ b/server/objects/mediaTypes/Podcast.js
@@ -166,7 +166,11 @@ class Podcast {
   }
 
   removeFileWithInode(inode) {
-    this.episodes = this.episodes.filter(ep => ep.audioFile.ino !== inode)
+    const hasEpisode = this.episodes.some(ep => ep.audioFile.ino === inode)
+    if (hasEpisode) {
+      this.episodes = this.episodes.filter(ep => ep.audioFile.ino !== inode)
+    }
+    return hasEpisode
   }
 
   findFileWithInode(inode) {
diff --git a/server/routers/ApiRouter.js b/server/routers/ApiRouter.js
index 7850adcb4..194833670 100644
--- a/server/routers/ApiRouter.js
+++ b/server/routers/ApiRouter.js
@@ -112,6 +112,7 @@ class ApiRouter {
     this.router.get('/items/:id/tone-object', LibraryItemController.middleware.bind(this), LibraryItemController.getToneMetadataObject.bind(this))
     this.router.post('/items/:id/chapters', LibraryItemController.middleware.bind(this), LibraryItemController.updateMediaChapters.bind(this))
     this.router.post('/items/:id/tone-scan/:index?', LibraryItemController.middleware.bind(this), LibraryItemController.toneScan.bind(this))
+    this.router.delete('/items/:id/file/:ino', LibraryItemController.middleware.bind(this), LibraryItemController.deleteLibraryFile.bind(this))
 
     this.router.post('/items/batch/delete', LibraryItemController.batchDelete.bind(this))
     this.router.post('/items/batch/update', LibraryItemController.batchUpdate.bind(this))