diff --git a/src/public/app/components/app_context.js b/src/public/app/components/app_context.js
index eae71d199..5cf1b35dd 100644
--- a/src/public/app/components/app_context.js
+++ b/src/public/app/components/app_context.js
@@ -76,6 +76,10 @@ class AppContext extends Component {
         $("body").append($renderedWidget);
 
         $renderedWidget.on('click', "[data-trigger-command]", function() {
+            if ($(this).hasClass("disabled")) {
+                return;
+            }
+
             const commandName = $(this).attr('data-trigger-command');
             const $component = $(this).closest(".component");
             const component = $component.prop("component");
diff --git a/src/public/app/desktop.js b/src/public/app/desktop.js
index 7b0da9e35..eb0ac2c21 100644
--- a/src/public/app/desktop.js
+++ b/src/public/app/desktop.js
@@ -4,11 +4,9 @@ import noteTooltipService from './services/note_tooltip.js';
 import bundleService from "./services/bundle.js";
 import noteAutocompleteService from './services/note_autocomplete.js';
 import macInit from './services/mac_init.js';
-import contextMenu from "./menus/context_menu.js";
+import electronContextMenu from "./menus/electron_context_menu.js";
 import DesktopLayout from "./layouts/desktop_layout.js";
 import glob from "./services/glob.js";
-import zoomService from './components/zoom.js';
-import options from "./services/options.js";
 
 bundleService.getWidgetBundlesByParent().then(widgetBundles => {
     appContext.setLayout(new DesktopLayout(widgetBundles));
@@ -18,9 +16,8 @@ bundleService.getWidgetBundlesByParent().then(widgetBundles => {
 glob.setupGlobs();
 
 if (utils.isElectron()) {
-    utils.dynamicRequire('electron').ipcRenderer.on('globalShortcut', async function(event, actionName) {
-        appContext.triggerCommand(actionName);
-    });
+    utils.dynamicRequire('electron').ipcRenderer.on('globalShortcut',
+        async (event, actionName) => appContext.triggerCommand(actionName));
 }
 
 macInit.init();
@@ -30,131 +27,5 @@ noteTooltipService.setupGlobalTooltip();
 noteAutocompleteService.init();
 
 if (utils.isElectron()) {
-    const electron = utils.dynamicRequire('electron');
-
-    const remote = utils.dynamicRequire('@electron/remote');
-    const {webContents} = remote.getCurrentWindow();
-
-    webContents.on('context-menu', (event, params) => {
-        const {editFlags} = params;
-        const hasText = params.selectionText.trim().length > 0;
-        const isMac = process.platform === "darwin";
-        const platformModifier = isMac ? 'Meta' : 'Ctrl';
-
-        const items = [];
-
-        if (params.misspelledWord) {
-            for (const suggestion of params.dictionarySuggestions) {
-                items.push({
-                    title: suggestion,
-                    command: "replaceMisspelling",
-                    spellingSuggestion: suggestion,
-                    uiIcon: "bx bx-empty"
-                });
-            }
-
-            items.push({
-                title: `Add "${params.misspelledWord}" to dictionary`,
-                uiIcon: "bx bx-plus",
-                handler: () => webContents.session.addWordToSpellCheckerDictionary(params.misspelledWord)
-            });
-
-            items.push({ title: `----` });
-        }
-
-        if (params.isEditable) {
-            items.push({
-                enabled: editFlags.canCut && hasText,
-                title: `Cut <kbd>${platformModifier}+X`,
-                uiIcon: "bx bx-cut",
-                handler: () => webContents.cut()
-            });
-        }
-
-        if (params.isEditable || hasText) {
-            items.push({
-                enabled: editFlags.canCopy && hasText,
-                title: `Copy <kbd>${platformModifier}+C`,
-                uiIcon: "bx bx-copy",
-                handler: () => webContents.copy()
-            });
-        }
-
-        if (!["", "javascript:", "about:blank#blocked"].includes(params.linkURL) && params.mediaType === 'none') {
-            items.push({
-                title: `Copy link`,
-                uiIcon: "bx bx-copy",
-                handler: () => {
-                    electron.clipboard.write({
-                        bookmark: params.linkText,
-                        text: params.linkURL
-                    });
-                }
-            });
-        }
-
-        if (params.isEditable) {
-            items.push({
-                enabled: editFlags.canPaste,
-                title: `Paste <kbd>${platformModifier}+V`,
-                uiIcon: "bx bx-paste",
-                handler: () => webContents.paste()
-            });
-        }
-
-        if (params.isEditable) {
-            items.push({
-                enabled: editFlags.canPaste,
-                title: `Paste as plain text <kbd>${platformModifier}+Shift+V`,
-                uiIcon: "bx bx-paste",
-                handler: () => webContents.pasteAndMatchStyle()
-            });
-        }
-
-        if (hasText) {
-            const shortenedSelection = params.selectionText.length > 15
-                ? (`${params.selectionText.substr(0, 13)}…`)
-                : params.selectionText;
-
-            // Read the search engine from the options and fallback to DuckDuckGo if the option is not set.
-            const customSearchEngineName = options.get("customSearchEngineName");
-            const customSearchEngineUrl = options.get("customSearchEngineUrl");
-            let searchEngineName;
-            let searchEngineUrl;
-            if (customSearchEngineName && customSearchEngineUrl) {
-                searchEngineName = customSearchEngineName;
-                searchEngineUrl = customSearchEngineUrl;
-            } else {
-                searchEngineName = "Duckduckgo";
-                searchEngineUrl = "https://duckduckgo.com/?q={keyword}";
-            }
-
-            // Replace the placeholder with the real search keyword.
-            let searchUrl = searchEngineUrl.replace("{keyword}", encodeURIComponent(params.selectionText));
-
-            items.push({
-                enabled: editFlags.canPaste,
-                title: `Search for "${shortenedSelection}" with ${searchEngineName}`,
-                uiIcon: "bx bx-search-alt",
-                handler: () => electron.shell.openExternal(searchUrl)
-            });
-        }
-
-        if (items.length === 0) {
-            return;
-        }
-
-        const zoomLevel = zoomService.getCurrentZoom();
-
-        contextMenu.show({
-            x: params.x / zoomLevel,
-            y: params.y / zoomLevel,
-            items,
-            selectMenuItemHandler: ({command, spellingSuggestion}) => {
-                if (command === 'replaceMisspelling') {
-                    webContents.insertText(spellingSuggestion);
-                }
-            }
-        });
-    });
+    electronContextMenu.setupContextMenu();
 }
diff --git a/src/public/app/menus/electron_context_menu.js b/src/public/app/menus/electron_context_menu.js
new file mode 100644
index 000000000..6c455020b
--- /dev/null
+++ b/src/public/app/menus/electron_context_menu.js
@@ -0,0 +1,138 @@
+import utils from "../services/utils.js";
+import options from "../services/options.js";
+import zoomService from "../components/zoom.js";
+import contextMenu from "./context_menu.js";
+
+function setupContextMenu() {
+    const electron = utils.dynamicRequire('electron');
+
+    const remote = utils.dynamicRequire('@electron/remote');
+    const {webContents} = remote.getCurrentWindow();
+
+    webContents.on('context-menu', (event, params) => {
+        const {editFlags} = params;
+        const hasText = params.selectionText.trim().length > 0;
+        const isMac = process.platform === "darwin";
+        const platformModifier = isMac ? 'Meta' : 'Ctrl';
+
+        const items = [];
+
+        if (params.misspelledWord) {
+            for (const suggestion of params.dictionarySuggestions) {
+                items.push({
+                    title: suggestion,
+                    command: "replaceMisspelling",
+                    spellingSuggestion: suggestion,
+                    uiIcon: "bx bx-empty"
+                });
+            }
+
+            items.push({
+                title: `Add "${params.misspelledWord}" to dictionary`,
+                uiIcon: "bx bx-plus",
+                handler: () => webContents.session.addWordToSpellCheckerDictionary(params.misspelledWord)
+            });
+
+            items.push({ title: `----` });
+        }
+
+        if (params.isEditable) {
+            items.push({
+                enabled: editFlags.canCut && hasText,
+                title: `Cut <kbd>${platformModifier}+X`,
+                uiIcon: "bx bx-cut",
+                handler: () => webContents.cut()
+            });
+        }
+
+        if (params.isEditable || hasText) {
+            items.push({
+                enabled: editFlags.canCopy && hasText,
+                title: `Copy <kbd>${platformModifier}+C`,
+                uiIcon: "bx bx-copy",
+                handler: () => webContents.copy()
+            });
+        }
+
+        if (!["", "javascript:", "about:blank#blocked"].includes(params.linkURL) && params.mediaType === 'none') {
+            items.push({
+                title: `Copy link`,
+                uiIcon: "bx bx-copy",
+                handler: () => {
+                    electron.clipboard.write({
+                        bookmark: params.linkText,
+                        text: params.linkURL
+                    });
+                }
+            });
+        }
+
+        if (params.isEditable) {
+            items.push({
+                enabled: editFlags.canPaste,
+                title: `Paste <kbd>${platformModifier}+V`,
+                uiIcon: "bx bx-paste",
+                handler: () => webContents.paste()
+            });
+        }
+
+        if (params.isEditable) {
+            items.push({
+                enabled: editFlags.canPaste,
+                title: `Paste as plain text <kbd>${platformModifier}+Shift+V`,
+                uiIcon: "bx bx-paste",
+                handler: () => webContents.pasteAndMatchStyle()
+            });
+        }
+
+        if (hasText) {
+            const shortenedSelection = params.selectionText.length > 15
+                ? (`${params.selectionText.substr(0, 13)}…`)
+                : params.selectionText;
+
+            // Read the search engine from the options and fallback to DuckDuckGo if the option is not set.
+            const customSearchEngineName = options.get("customSearchEngineName");
+            const customSearchEngineUrl = options.get("customSearchEngineUrl");
+            let searchEngineName;
+            let searchEngineUrl;
+            if (customSearchEngineName && customSearchEngineUrl) {
+                searchEngineName = customSearchEngineName;
+                searchEngineUrl = customSearchEngineUrl;
+            } else {
+                searchEngineName = "Duckduckgo";
+                searchEngineUrl = "https://duckduckgo.com/?q={keyword}";
+            }
+
+            // Replace the placeholder with the real search keyword.
+            let searchUrl = searchEngineUrl.replace("{keyword}", encodeURIComponent(params.selectionText));
+
+            items.push({
+                enabled: editFlags.canPaste,
+                title: `Search for "${shortenedSelection}" with ${searchEngineName}`,
+                uiIcon: "bx bx-search-alt",
+                handler: () => electron.shell.openExternal(searchUrl)
+            });
+        }
+
+        if (items.length === 0) {
+            return;
+        }
+
+        const zoomLevel = zoomService.getCurrentZoom();
+
+        contextMenu.show({
+            x: params.x / zoomLevel,
+            y: params.y / zoomLevel,
+            items,
+            selectMenuItemHandler: ({command, spellingSuggestion}) => {
+                if (command === 'replaceMisspelling') {
+                    webContents.insertText(spellingSuggestion);
+                }
+            }
+        });
+    });
+}
+
+export default {
+    setupContextMenu
+};
diff --git a/src/public/app/services/note_tooltip.js b/src/public/app/services/note_tooltip.js
index f0cf15651..70f4a1c2e 100644
--- a/src/public/app/services/note_tooltip.js
+++ b/src/public/app/services/note_tooltip.js
@@ -27,7 +27,7 @@ async function mouseEnterHandler() {
         return;
     }
 
-    // this is to avoid showing tooltip from inside CKEditor link editor dialog
+    // this is to avoid showing tooltip from inside the CKEditor link editor dialog
     if ($link.closest(".ck-link-actions").length) {
         return;
     }
diff --git a/src/public/app/widgets/attachment_detail.js b/src/public/app/widgets/attachment_detail.js
index 4030ba2c6..8f4b9e43d 100644
--- a/src/public/app/widgets/attachment_detail.js
+++ b/src/public/app/widgets/attachment_detail.js
@@ -67,13 +67,13 @@ const TPL = `
 </div>`;
 
 export default class AttachmentDetailWidget extends BasicWidget {
-    constructor(attachment) {
+    constructor(attachment, isFullDetail) {
         super();
 
         this.contentSized();
         this.attachment = attachment;
-        this.attachmentActionsWidget = new AttachmentActionsWidget(attachment);
-        this.isFullDetail = true;
+        this.attachmentActionsWidget = new AttachmentActionsWidget(attachment, isFullDetail);
+        this.isFullDetail = isFullDetail;
         this.child(this.attachmentActionsWidget);
     }
 
diff --git a/src/public/app/widgets/buttons/attachments_actions.js b/src/public/app/widgets/buttons/attachments_actions.js
index 1e8240e78..6a909e0ac 100644
--- a/src/public/app/widgets/buttons/attachments_actions.js
+++ b/src/public/app/widgets/buttons/attachments_actions.js
@@ -29,10 +29,8 @@ const TPL = `
         aria-expanded="false" class="icon-action icon-action-always-border bx bx-dots-vertical-rounded"></button>
 
     <div class="dropdown-menu dropdown-menu-right">
-        <a data-trigger-command="openAttachment" class="dropdown-item">Open</a>
-        <a data-trigger-command="openAttachmentExternally" class="dropdown-item"
-           title="File will be open in an external application and watched for changes. You'll then be able to upload the modified version back to Trilium.">
-            Open externally</a>
+        <a data-trigger-command="openAttachment" class="dropdown-item"
+            title="File will be open in an external application and watched for changes. You'll then be able to upload the modified version back to Trilium.">Open externally</a>
         <a data-trigger-command="downloadAttachment" class="dropdown-item">Download</a>
         <a data-trigger-command="uploadNewAttachmentRevision" class="dropdown-item">Upload new revision</a>
         <a data-trigger-command="copyAttachmentReferenceToClipboard" class="dropdown-item">Copy reference to clipboard</a>
@@ -44,10 +42,11 @@ const TPL = `
 </div>`;
 
 export default class AttachmentActionsWidget extends BasicWidget {
-    constructor(attachment) {
+    constructor(attachment, isFullDetail) {
         super();
 
         this.attachment = attachment;
+        this.isFullDetail = isFullDetail;
     }
 
     get attachmentId() {
@@ -83,6 +82,17 @@ export default class AttachmentActionsWidget extends BasicWidget {
                 toastService.showError("Upload of a new attachment revision failed.");
             }
         });
+
+        if (!this.isFullDetail) {
+            // we deactivate this button because the WatchedFileUpdateStatusWidget assumes only one visible attachment
+            // in a note context, so it doesn't work in a list
+            const $openAttachmentButton = this.$widget.find("[data-trigger-command='openAttachment']");
+            $openAttachmentButton
+                .addClass("disabled")
+                .append($('<span class="disabled-tooltip"> (?)</span>')
+                    .attr("title", "Opening attachment externally is available only from the detail page, please first click on the attachment detail first and repeat the action.")
+                );
+        }
     }
 
     async openAttachmentCommand() {
@@ -101,10 +111,6 @@ export default class AttachmentActionsWidget extends BasicWidget {
         this.parent.copyAttachmentReferenceToClipboard();
     }
 
-    async openAttachmentExternallyCommand() {
-        await openService.openAttachmentExternally(this.attachmentId, this.attachment.mime);
-    }
-
     async deleteAttachmentCommand() {
         if (!await dialogService.confirm(`Are you sure you want to delete attachment '${this.attachment.title}'?`)) {
             return;
diff --git a/src/public/app/widgets/type_widgets/attachment_detail.js b/src/public/app/widgets/type_widgets/attachment_detail.js
index 449ad9323..b74b2cfa8 100644
--- a/src/public/app/widgets/type_widgets/attachment_detail.js
+++ b/src/public/app/widgets/type_widgets/attachment_detail.js
@@ -37,8 +37,7 @@ export default class AttachmentDetailTypeWidget extends TypeWidget {
             return;
         }
 
-        const attachmentDetailWidget = new AttachmentDetailWidget(attachment);
-        attachmentDetailWidget.isFullDetail = true;
+        const attachmentDetailWidget = new AttachmentDetailWidget(attachment, true);
         this.child(attachmentDetailWidget);
 
         this.$wrapper.append(attachmentDetailWidget.render());
diff --git a/src/public/app/widgets/type_widgets/attachment_list.js b/src/public/app/widgets/type_widgets/attachment_list.js
index e4876e995..1604ea313 100644
--- a/src/public/app/widgets/type_widgets/attachment_list.js
+++ b/src/public/app/widgets/type_widgets/attachment_list.js
@@ -39,8 +39,7 @@ export default class AttachmentListTypeWidget extends TypeWidget {
         }
 
         for (const attachment of attachments) {
-            const attachmentDetailWidget = new AttachmentDetailWidget(attachment);
-            attachmentDetailWidget.isFullDetail = false;
+            const attachmentDetailWidget = new AttachmentDetailWidget(attachment, false);
 
             this.child(attachmentDetailWidget);
 
diff --git a/src/public/app/widgets/watched_file_update_status.js b/src/public/app/widgets/watched_file_update_status.js
index 7e2818ac4..05e5567e7 100644
--- a/src/public/app/widgets/watched_file_update_status.js
+++ b/src/public/app/widgets/watched_file_update_status.js
@@ -12,7 +12,7 @@ const TPL = `
     </style>
     
     <p>File <code class="file-path"></code> has been last modified on <span class="file-last-modified"></span>.</p> 
-        
+
     <div style="display: flex; flex-direction: row; justify-content: space-evenly;">
         <button class="btn btn-sm file-upload-button">Upload modified file</button>
         
diff --git a/src/public/stylesheets/style.css b/src/public/stylesheets/style.css
index 02c3edc1a..f0d90056b 100644
--- a/src/public/stylesheets/style.css
+++ b/src/public/stylesheets/style.css
@@ -195,6 +195,12 @@ div.ui-tooltip {
     pointer-events: none;
 }
 
+.dropdown-menu .disabled .disabled-tooltip {
+    pointer-events: all;
+    color: var(--menu-text-color);
+    cursor: help;
+}
+
 .dropdown-menu a:hover:not(.disabled), .dropdown-item:hover:not(.disabled) {
     color: var(--hover-item-text-color) !important;
     background-color: var(--hover-item-background-color) !important;