diff --git a/Userland/Libraries/LibWebView/OutOfProcessWebView.cpp b/Userland/Libraries/LibWebView/OutOfProcessWebView.cpp
index 640b4109fc..2077f283a6 100644
--- a/Userland/Libraries/LibWebView/OutOfProcessWebView.cpp
+++ b/Userland/Libraries/LibWebView/OutOfProcessWebView.cpp
@@ -348,20 +348,22 @@ void OutOfProcessWebView::notify_server_did_request_image_context_menu(Badge<Web
 void OutOfProcessWebView::notify_server_did_request_alert(Badge<WebContentClient>, String const& message)
 {
     GUI::MessageBox::show(window(), message, "Alert"sv, GUI::MessageBox::Type::Information);
+    client().async_alert_closed();
 }
 
-bool OutOfProcessWebView::notify_server_did_request_confirm(Badge<WebContentClient>, String const& message)
+void OutOfProcessWebView::notify_server_did_request_confirm(Badge<WebContentClient>, String const& message)
 {
     auto confirm_result = GUI::MessageBox::show(window(), message, "Confirm"sv, GUI::MessageBox::Type::Warning, GUI::MessageBox::InputType::OKCancel);
-    return confirm_result == GUI::Dialog::ExecResult::OK;
+    client().async_confirm_closed(confirm_result == GUI::Dialog::ExecResult::OK);
 }
 
-String OutOfProcessWebView::notify_server_did_request_prompt(Badge<WebContentClient>, String const& message, String const& default_)
+void OutOfProcessWebView::notify_server_did_request_prompt(Badge<WebContentClient>, String const& message, String const& default_)
 {
     String response { default_ };
     if (GUI::InputBox::show(window(), response, message, "Prompt"sv) == GUI::InputBox::ExecResult::OK)
-        return response;
-    return {};
+        client().async_prompt_closed(move(response));
+    else
+        client().async_prompt_closed({});
 }
 
 void OutOfProcessWebView::notify_server_did_get_source(const AK::URL& url, String const& source)
diff --git a/Userland/Libraries/LibWebView/OutOfProcessWebView.h b/Userland/Libraries/LibWebView/OutOfProcessWebView.h
index 8ee72fcad8..9d6370bff1 100644
--- a/Userland/Libraries/LibWebView/OutOfProcessWebView.h
+++ b/Userland/Libraries/LibWebView/OutOfProcessWebView.h
@@ -156,8 +156,8 @@ private:
     virtual void notify_server_did_request_link_context_menu(Badge<WebContentClient>, Gfx::IntPoint const&, const AK::URL&, String const& target, unsigned modifiers) override;
     virtual void notify_server_did_request_image_context_menu(Badge<WebContentClient>, Gfx::IntPoint const&, const AK::URL&, String const& target, unsigned modifiers, Gfx::ShareableBitmap const&) override;
     virtual void notify_server_did_request_alert(Badge<WebContentClient>, String const& message) override;
-    virtual bool notify_server_did_request_confirm(Badge<WebContentClient>, String const& message) override;
-    virtual String notify_server_did_request_prompt(Badge<WebContentClient>, String const& message, String const& default_) override;
+    virtual void notify_server_did_request_confirm(Badge<WebContentClient>, String const& message) override;
+    virtual void notify_server_did_request_prompt(Badge<WebContentClient>, String const& message, String const& default_) override;
     virtual void notify_server_did_get_source(const AK::URL& url, String const& source) override;
     virtual void notify_server_did_get_dom_tree(String const& dom_tree) override;
     virtual void notify_server_did_get_dom_node_properties(i32 node_id, String const& specified_style, String const& computed_style, String const& custom_properties, String const& node_box_sizing) override;
diff --git a/Userland/Libraries/LibWebView/ViewImplementation.h b/Userland/Libraries/LibWebView/ViewImplementation.h
index 4d72c53af6..43a41dacf7 100644
--- a/Userland/Libraries/LibWebView/ViewImplementation.h
+++ b/Userland/Libraries/LibWebView/ViewImplementation.h
@@ -42,8 +42,8 @@ public:
     virtual void notify_server_did_request_link_context_menu(Badge<WebContentClient>, Gfx::IntPoint const&, const AK::URL&, String const& target, unsigned modifiers) = 0;
     virtual void notify_server_did_request_image_context_menu(Badge<WebContentClient>, Gfx::IntPoint const&, const AK::URL&, String const& target, unsigned modifiers, Gfx::ShareableBitmap const&) = 0;
     virtual void notify_server_did_request_alert(Badge<WebContentClient>, String const& message) = 0;
-    virtual bool notify_server_did_request_confirm(Badge<WebContentClient>, String const& message) = 0;
-    virtual String notify_server_did_request_prompt(Badge<WebContentClient>, String const& message, String const& default_) = 0;
+    virtual void notify_server_did_request_confirm(Badge<WebContentClient>, String const& message) = 0;
+    virtual void notify_server_did_request_prompt(Badge<WebContentClient>, String const& message, String const& default_) = 0;
     virtual void notify_server_did_get_source(const AK::URL& url, String const& source) = 0;
     virtual void notify_server_did_get_dom_tree(String const& dom_tree) = 0;
     virtual void notify_server_did_get_dom_node_properties(i32 node_id, String const& specified_style, String const& computed_style, String const& custom_properties, String const& node_box_sizing) = 0;
diff --git a/Userland/Libraries/LibWebView/WebContentClient.cpp b/Userland/Libraries/LibWebView/WebContentClient.cpp
index bea1d30057..ec579542c8 100644
--- a/Userland/Libraries/LibWebView/WebContentClient.cpp
+++ b/Userland/Libraries/LibWebView/WebContentClient.cpp
@@ -181,14 +181,14 @@ void WebContentClient::did_request_alert(String const& message)
     m_view.notify_server_did_request_alert({}, message);
 }
 
-Messages::WebContentClient::DidRequestConfirmResponse WebContentClient::did_request_confirm(String const& message)
+void WebContentClient::did_request_confirm(String const& message)
 {
-    return m_view.notify_server_did_request_confirm({}, message);
+    m_view.notify_server_did_request_confirm({}, message);
 }
 
-Messages::WebContentClient::DidRequestPromptResponse WebContentClient::did_request_prompt(String const& message, String const& default_)
+void WebContentClient::did_request_prompt(String const& message, String const& default_)
 {
-    return m_view.notify_server_did_request_prompt({}, message, default_);
+    m_view.notify_server_did_request_prompt({}, message, default_);
 }
 
 void WebContentClient::did_change_favicon(Gfx::ShareableBitmap const& favicon)
diff --git a/Userland/Libraries/LibWebView/WebContentClient.h b/Userland/Libraries/LibWebView/WebContentClient.h
index 5f05a31c4a..7c53edea82 100644
--- a/Userland/Libraries/LibWebView/WebContentClient.h
+++ b/Userland/Libraries/LibWebView/WebContentClient.h
@@ -58,8 +58,8 @@ private:
     virtual void did_get_js_console_messages(i32 start_index, Vector<String> const& message_types, Vector<String> const& messages) override;
     virtual void did_change_favicon(Gfx::ShareableBitmap const&) override;
     virtual void did_request_alert(String const&) override;
-    virtual Messages::WebContentClient::DidRequestConfirmResponse did_request_confirm(String const&) override;
-    virtual Messages::WebContentClient::DidRequestPromptResponse did_request_prompt(String const&, String const&) override;
+    virtual void did_request_confirm(String const&) override;
+    virtual void did_request_prompt(String const&, String const&) override;
     virtual Messages::WebContentClient::DidRequestAllCookiesResponse did_request_all_cookies(AK::URL const&) override;
     virtual Messages::WebContentClient::DidRequestNamedCookieResponse did_request_named_cookie(AK::URL const&, String const&) override;
     virtual Messages::WebContentClient::DidRequestCookieResponse did_request_cookie(AK::URL const&, u8) override;
diff --git a/Userland/Services/WebContent/ConnectionFromClient.cpp b/Userland/Services/WebContent/ConnectionFromClient.cpp
index 5d31679859..420c432f5b 100644
--- a/Userland/Services/WebContent/ConnectionFromClient.cpp
+++ b/Userland/Services/WebContent/ConnectionFromClient.cpp
@@ -576,4 +576,19 @@ void ConnectionFromClient::set_system_visibility_state(bool visible)
             : Web::HTML::VisibilityState::Hidden);
 }
 
+void ConnectionFromClient::alert_closed()
+{
+    m_page_host->alert_closed();
+}
+
+void ConnectionFromClient::confirm_closed(bool accepted)
+{
+    m_page_host->confirm_closed(accepted);
+}
+
+void ConnectionFromClient::prompt_closed(String const& response)
+{
+    m_page_host->prompt_closed(response);
+}
+
 }
diff --git a/Userland/Services/WebContent/ConnectionFromClient.h b/Userland/Services/WebContent/ConnectionFromClient.h
index 3de21bb633..d6194eebb0 100644
--- a/Userland/Services/WebContent/ConnectionFromClient.h
+++ b/Userland/Services/WebContent/ConnectionFromClient.h
@@ -84,6 +84,10 @@ private:
     virtual void run_javascript(String const&) override;
     virtual void js_console_request_messages(i32) override;
 
+    virtual void alert_closed() override;
+    virtual void confirm_closed(bool accepted) override;
+    virtual void prompt_closed(String const& response) override;
+
     virtual Messages::WebContentServer::TakeDocumentScreenshotResponse take_document_screenshot() override;
 
     virtual Messages::WebContentServer::GetLocalStorageEntriesResponse get_local_storage_entries() override;
diff --git a/Userland/Services/WebContent/PageHost.cpp b/Userland/Services/WebContent/PageHost.cpp
index 8e48db996d..f328109226 100644
--- a/Userland/Services/WebContent/PageHost.cpp
+++ b/Userland/Services/WebContent/PageHost.cpp
@@ -7,13 +7,17 @@
 
 #include "PageHost.h"
 #include "ConnectionFromClient.h"
+#include <AK/SourceLocation.h>
 #include <LibGfx/Painter.h>
 #include <LibGfx/ShareableBitmap.h>
 #include <LibGfx/SystemTheme.h>
 #include <LibWeb/Cookie/ParsedCookie.h>
 #include <LibWeb/HTML/BrowsingContext.h>
+#include <LibWeb/HTML/EventLoop/EventLoop.h>
+#include <LibWeb/HTML/Scripting/Environments.h>
 #include <LibWeb/Layout/InitialContainingBlock.h>
 #include <LibWeb/Painting/PaintableBox.h>
+#include <LibWeb/Platform/EventLoopPlugin.h>
 #include <LibWeb/Platform/Timer.h>
 #include <WebContent/WebContentClientEndpoint.h>
 #include <WebContent/WebDriverConnection.h>
@@ -233,33 +237,72 @@ void PageHost::page_did_request_link_context_menu(Gfx::IntPoint const& content_p
     m_client.async_did_request_link_context_menu(content_position, url, target, modifiers);
 }
 
+template<typename ResponseType>
+static ResponseType spin_event_loop_until_dialog_closed(ConnectionFromClient& client, Optional<ResponseType>& response, SourceLocation location = SourceLocation::current())
+{
+    auto& event_loop = Web::HTML::current_settings_object().responsible_event_loop();
+
+    ScopeGuard guard { [&] { event_loop.set_execution_paused(false); } };
+    event_loop.set_execution_paused(true);
+
+    Web::Platform::EventLoopPlugin::the().spin_until([&]() {
+        return response.has_value() || !client.is_open();
+    });
+
+    if (!client.is_open()) {
+        dbgln("WebContent client disconnected during {}. Exiting peacefully.", location.function_name());
+        exit(0);
+    }
+
+    return response.release_value();
+}
+
 void PageHost::page_did_request_alert(String const& message)
 {
-    auto response = m_client.send_sync_but_allow_failure<Messages::WebContentClient::DidRequestAlert>(message);
-    if (!response) {
-        dbgln("WebContent client disconnected during DidRequestAlert. Exiting peacefully.");
-        exit(0);
+    m_pending_dialog = PendingDialog::Alert;
+    m_client.async_did_request_alert(message);
+
+    spin_event_loop_until_dialog_closed(m_client, m_pending_alert_response);
+}
+
+void PageHost::alert_closed()
+{
+    if (m_pending_dialog == PendingDialog::Alert) {
+        m_pending_dialog = PendingDialog::None;
+        m_pending_alert_response = Empty {};
     }
 }
 
 bool PageHost::page_did_request_confirm(String const& message)
 {
-    auto response = m_client.send_sync_but_allow_failure<Messages::WebContentClient::DidRequestConfirm>(message);
-    if (!response) {
-        dbgln("WebContent client disconnected during DidRequestConfirm. Exiting peacefully.");
-        exit(0);
+    m_pending_dialog = PendingDialog::Confirm;
+    m_client.async_did_request_confirm(message);
+
+    return spin_event_loop_until_dialog_closed(m_client, m_pending_confirm_response);
+}
+
+void PageHost::confirm_closed(bool accepted)
+{
+    if (m_pending_dialog == PendingDialog::Confirm) {
+        m_pending_dialog = PendingDialog::None;
+        m_pending_confirm_response = accepted;
     }
-    return response->take_result();
 }
 
 String PageHost::page_did_request_prompt(String const& message, String const& default_)
 {
-    auto response = m_client.send_sync_but_allow_failure<Messages::WebContentClient::DidRequestPrompt>(message, default_);
-    if (!response) {
-        dbgln("WebContent client disconnected during DidRequestPrompt. Exiting peacefully.");
-        exit(0);
+    m_pending_dialog = PendingDialog::Prompt;
+    m_client.async_did_request_prompt(message, default_);
+
+    return spin_event_loop_until_dialog_closed(m_client, m_pending_prompt_response);
+}
+
+void PageHost::prompt_closed(String response)
+{
+    if (m_pending_dialog == PendingDialog::Prompt) {
+        m_pending_dialog = PendingDialog::None;
+        m_pending_prompt_response = move(response);
     }
-    return response->take_response();
 }
 
 void PageHost::page_did_change_favicon(Gfx::Bitmap const& favicon)
diff --git a/Userland/Services/WebContent/PageHost.h b/Userland/Services/WebContent/PageHost.h
index f40222f958..15ba8fc6fc 100644
--- a/Userland/Services/WebContent/PageHost.h
+++ b/Userland/Services/WebContent/PageHost.h
@@ -43,6 +43,19 @@ public:
 
     ErrorOr<void> connect_to_webdriver(String const& webdriver_ipc_path);
 
+    void alert_closed();
+    void confirm_closed(bool accepted);
+    void prompt_closed(String response);
+
+    enum class PendingDialog {
+        None,
+        Alert,
+        Confirm,
+        Prompt,
+    };
+    bool has_pending_dialog() const { return m_pending_dialog != PendingDialog::None; }
+    PendingDialog pending_dialog() const { return m_pending_dialog; }
+
 private:
     // ^PageClient
     virtual Gfx::Palette palette() const override;
@@ -95,6 +108,11 @@ private:
     Web::CSS::PreferredColorScheme m_preferred_color_scheme { Web::CSS::PreferredColorScheme::Auto };
 
     RefPtr<WebDriverConnection> m_webdriver;
+
+    PendingDialog m_pending_dialog { PendingDialog::None };
+    Optional<Empty> m_pending_alert_response;
+    Optional<bool> m_pending_confirm_response;
+    Optional<String> m_pending_prompt_response;
 };
 
 }
diff --git a/Userland/Services/WebContent/WebContentClient.ipc b/Userland/Services/WebContent/WebContentClient.ipc
index fa770e8400..6fa9c350a6 100644
--- a/Userland/Services/WebContent/WebContentClient.ipc
+++ b/Userland/Services/WebContent/WebContentClient.ipc
@@ -29,9 +29,9 @@ endpoint WebContentClient
     did_request_context_menu(Gfx::IntPoint content_position) =|
     did_request_link_context_menu(Gfx::IntPoint content_position, URL url, String target, unsigned modifiers) =|
     did_request_image_context_menu(Gfx::IntPoint content_position, URL url, String target, unsigned modifiers, Gfx::ShareableBitmap bitmap) =|
-    did_request_alert(String message) => ()
-    did_request_confirm(String message) => (bool result)
-    did_request_prompt(String message, String default_) => (String response)
+    did_request_alert(String message) =|
+    did_request_confirm(String message) =|
+    did_request_prompt(String message, String default_) =|
     did_get_source(URL url, String source) =|
     did_get_dom_tree(String dom_tree) =|
     did_get_dom_node_properties(i32 node_id, String specified_style, String computed_style, String custom_properties, String node_box_sizing_json) =|
diff --git a/Userland/Services/WebContent/WebContentServer.ipc b/Userland/Services/WebContent/WebContentServer.ipc
index 4e311de7cb..45d70f5356 100644
--- a/Userland/Services/WebContent/WebContentServer.ipc
+++ b/Userland/Services/WebContent/WebContentServer.ipc
@@ -65,4 +65,8 @@ endpoint WebContentServer
     handle_file_return(i32 error, Optional<IPC::File> file, i32 request_id) =|
 
     set_system_visibility_state(bool visible) =|
+
+    alert_closed() =|
+    confirm_closed(bool accepted) =|
+    prompt_closed(String response) =|
 }