diff --git a/chrome/content/zotero/reader.xhtml b/chrome/content/zotero/reader.xhtml
index 6301c630d0..a25b90ffe1 100644
--- a/chrome/content/zotero/reader.xhtml
+++ b/chrome/content/zotero/reader.xhtml
@@ -94,7 +94,7 @@
 
 	<tooltip id="iframeTooltip" page="true"/>
 	<menubar>
-		<menu id="fileMenu" label="&fileMenu.label;" accesskey="&fileMenu.accesskey;">
+		<menu id="fileMenu" label="&fileMenu.label;" accesskey="&fileMenu.accesskey;" onpopupshowing="onFileMenuOpen()">
 			<menupopup id="menu_FilePopup">
 				<menuitem
 						id="menu_transferFromPDF"
diff --git a/chrome/content/zotero/xpcom/reader.js b/chrome/content/zotero/xpcom/reader.js
index 4e4293dcab..7117905b13 100644
--- a/chrome/content/zotero/xpcom/reader.js
+++ b/chrome/content/zotero/xpcom/reader.js
@@ -1215,6 +1215,7 @@ class ReaderWindow extends ReaderInstance {
 		this._window.addEventListener('DOMContentLoaded', (event) => {
 			if (event.target === this._window.document) {
 				this._popupset = this._window.document.getElementById('zotero-reader-popupset');
+				this._window.onFileMenuOpen = this._onFileMenuOpen.bind(this);
 				this._window.onGoMenuOpen = this._onGoMenuOpen.bind(this);
 				this._window.onViewMenuOpen = this._onViewMenuOpen.bind(this);
 				this._window.reader = this;
@@ -1251,6 +1252,22 @@ class ReaderWindow extends ReaderInstance {
 		this._window.document.title = title;
 	}
 
+	_onFileMenuOpen() {
+		let item = Zotero.Items.get(this._item.id);
+		let library = Zotero.Libraries.get(item.libraryID);
+		if (item
+			&& library.filesEditable
+			&& library.editable
+			&& !(item.deleted || item.parentItem && item.parentItem.deleted)) {
+			let annotations = item.getAnnotations();
+			let canTransferFromPDF = annotations.find(x => x.annotationIsExternal);
+			this._window.document.getElementById('menu_transferFromPDF').setAttribute('disabled', !canTransferFromPDF);
+		}
+		else {
+			this._window.document.getElementById('menu_transferFromPDF').setAttribute('disabled', true);
+		}
+	}
+
 	_onViewMenuOpen() {
 		if (this._type === 'pdf' || this._type === 'epub') {
 			this._window.document.getElementById('view-menuitem-no-spreads').setAttribute('checked', this._internalReader.spreadMode === 0);