diff --git a/editor/src/messages/layout/utility_types/widgets/menu_widgets.rs b/editor/src/messages/layout/utility_types/widgets/menu_widgets.rs
index a321876f..3f0855e9 100644
--- a/editor/src/messages/layout/utility_types/widgets/menu_widgets.rs
+++ b/editor/src/messages/layout/utility_types/widgets/menu_widgets.rs
@@ -37,12 +37,14 @@ pub struct MenuBarEntry {
 	pub shortcut: Option<ActionKeys>,
 	pub action: WidgetHolder,
 	pub children: MenuBarEntryChildren,
+	pub disabled: bool,
 }
 
 impl MenuBarEntry {
-	pub fn new_root(label: String, children: MenuBarEntryChildren) -> Self {
+	pub fn new_root(label: String, disabled: bool, children: MenuBarEntryChildren) -> Self {
 		Self {
 			label,
+			disabled,
 			children,
 			..Default::default()
 		}
@@ -67,6 +69,7 @@ impl Default for MenuBarEntry {
 			shortcut: None,
 			action: MenuBarEntry::no_action(),
 			children: MenuBarEntryChildren::empty(),
+			disabled: false,
 		}
 	}
 }
diff --git a/editor/src/messages/portfolio/menu_bar/menu_bar_message_handler.rs b/editor/src/messages/portfolio/menu_bar/menu_bar_message_handler.rs
index d147ef74..e4e09d50 100644
--- a/editor/src/messages/portfolio/menu_bar/menu_bar_message_handler.rs
+++ b/editor/src/messages/portfolio/menu_bar/menu_bar_message_handler.rs
@@ -6,12 +6,15 @@ use crate::messages::portfolio::document::utility_types::clipboards::Clipboard;
 use crate::messages::prelude::*;
 
 #[derive(Debug, Clone, Default)]
-pub struct MenuBarMessageHandler {}
+pub struct MenuBarMessageHandler {
+	no_active_document: bool,
+}
 
-impl MessageHandler<MenuBarMessage, ()> for MenuBarMessageHandler {
+impl MessageHandler<MenuBarMessage, bool> for MenuBarMessageHandler {
 	#[remain::check]
-	fn process_message(&mut self, message: MenuBarMessage, responses: &mut VecDeque<Message>, _data: ()) {
+	fn process_message(&mut self, message: MenuBarMessage, responses: &mut VecDeque<Message>, has_active_document: bool) {
 		use MenuBarMessage::*;
+		self.no_active_document = !has_active_document;
 
 		#[remain::sorted]
 		match message {
@@ -26,75 +29,13 @@ impl MessageHandler<MenuBarMessage, ()> for MenuBarMessageHandler {
 
 impl PropertyHolder for MenuBarMessageHandler {
 	fn properties(&self) -> Layout {
-		Layout::MenuLayout(MenuLayout::new(vec![
-			MenuBarEntry {
-				icon: Some("GraphiteLogo".into()),
-				action: MenuBarEntry::create_action(|_| FrontendMessage::TriggerVisitLink { url: "https://graphite.rs".into() }.into()),
-				..Default::default()
-			},
-			MenuBarEntry::new_root(
-				"File".into(),
-				MenuBarEntryChildren(vec![
-					vec![
-						MenuBarEntry {
-							label: "New…".into(),
-							icon: Some("File".into()),
-							action: MenuBarEntry::create_action(|_| DialogMessage::RequestNewDocumentDialog.into()),
-							shortcut: action_keys!(DialogMessageDiscriminant::RequestNewDocumentDialog),
-							children: MenuBarEntryChildren::empty(),
-						},
-						MenuBarEntry {
-							label: "Open…".into(),
-							shortcut: action_keys!(PortfolioMessageDiscriminant::OpenDocument),
-							action: MenuBarEntry::create_action(|_| PortfolioMessage::OpenDocument.into()),
-							..MenuBarEntry::default()
-						},
-					],
-					vec![
-						MenuBarEntry {
-							label: "Close".into(),
-							shortcut: action_keys!(PortfolioMessageDiscriminant::CloseActiveDocumentWithConfirmation),
-							action: MenuBarEntry::create_action(|_| PortfolioMessage::CloseActiveDocumentWithConfirmation.into()),
-							..MenuBarEntry::default()
-						},
-						MenuBarEntry {
-							label: "Close All".into(),
-							shortcut: action_keys!(DialogMessageDiscriminant::CloseAllDocumentsWithConfirmation),
-							action: MenuBarEntry::create_action(|_| DialogMessage::CloseAllDocumentsWithConfirmation.into()),
-							..MenuBarEntry::default()
-						},
-					],
-					vec![MenuBarEntry {
-						label: "Save".into(),
-						shortcut: action_keys!(DocumentMessageDiscriminant::SaveDocument),
-						action: MenuBarEntry::create_action(|_| DocumentMessage::SaveDocument.into()),
-						..MenuBarEntry::default()
-					}],
-					vec![
-						MenuBarEntry {
-							label: "Import…".into(),
-							shortcut: action_keys!(PortfolioMessageDiscriminant::Import),
-							action: MenuBarEntry::create_action(|_| PortfolioMessage::Import.into()),
-							..MenuBarEntry::default()
-						},
-						MenuBarEntry {
-							label: "Export…".into(),
-							shortcut: action_keys!(DialogMessageDiscriminant::RequestExportDialog),
-							action: MenuBarEntry::create_action(|_| DialogMessage::RequestExportDialog.into()),
-							..MenuBarEntry::default()
-						},
-					],
-					vec![MenuBarEntry {
-						label: "Preferences…".into(),
-						icon: Some("Settings".into()),
-						shortcut: action_keys!(DialogMessageDiscriminant::RequestPreferencesDialog),
-						action: MenuBarEntry::create_action(|_| DialogMessage::RequestPreferencesDialog.into()),
-						..MenuBarEntry::default()
-					}],
-				]),
-			),
+		let no_active_document = self.no_active_document;
+
+		// enable these only if there's an active document
+		let conditional_menu_entries = vec![
 			MenuBarEntry::new_root(
 				"Edit".into(),
+				no_active_document,
 				MenuBarEntryChildren(vec![
 					vec![
 						MenuBarEntry {
@@ -136,6 +77,7 @@ impl PropertyHolder for MenuBarMessageHandler {
 			),
 			MenuBarEntry::new_root(
 				"Layer".into(),
+				no_active_document,
 				MenuBarEntryChildren(vec![
 					vec![
 						MenuBarEntry {
@@ -213,6 +155,7 @@ impl PropertyHolder for MenuBarMessageHandler {
 			),
 			MenuBarEntry::new_root(
 				"Document".into(),
+				no_active_document,
 				MenuBarEntryChildren(vec![vec![MenuBarEntry {
 					label: "Clear Artboards".into(),
 					action: MenuBarEntry::create_action(|_| ArtboardMessage::ClearArtboards.into()),
@@ -221,6 +164,7 @@ impl PropertyHolder for MenuBarMessageHandler {
 			),
 			MenuBarEntry::new_root(
 				"View".into(),
+				no_active_document,
 				MenuBarEntryChildren(vec![vec![
 					MenuBarEntry {
 						label: "Zoom to Selected".into(),
@@ -248,8 +192,84 @@ impl PropertyHolder for MenuBarMessageHandler {
 					},
 				]]),
 			),
+		];
+
+		let mut menu_bar_entries = vec![
+			MenuBarEntry {
+				icon: Some("GraphiteLogo".into()),
+				action: MenuBarEntry::create_action(|_| FrontendMessage::TriggerVisitLink { url: "https://graphite.rs".into() }.into()),
+				..Default::default()
+			},
+			MenuBarEntry::new_root(
+				"File".into(),
+				false,
+				MenuBarEntryChildren(vec![
+					vec![
+						MenuBarEntry {
+							label: "New…".into(),
+							icon: Some("File".into()),
+							action: MenuBarEntry::create_action(|_| DialogMessage::RequestNewDocumentDialog.into()),
+							shortcut: action_keys!(DialogMessageDiscriminant::RequestNewDocumentDialog),
+							children: MenuBarEntryChildren::empty(),
+							..MenuBarEntry::default()
+						},
+						MenuBarEntry {
+							label: "Open…".into(),
+							shortcut: action_keys!(PortfolioMessageDiscriminant::OpenDocument),
+							action: MenuBarEntry::create_action(|_| PortfolioMessage::OpenDocument.into()),
+							..MenuBarEntry::default()
+						},
+					],
+					vec![
+						MenuBarEntry {
+							label: "Close".into(),
+							shortcut: action_keys!(PortfolioMessageDiscriminant::CloseActiveDocumentWithConfirmation),
+							action: MenuBarEntry::create_action(|_| PortfolioMessage::CloseActiveDocumentWithConfirmation.into()),
+							disabled: no_active_document,
+							..MenuBarEntry::default()
+						},
+						MenuBarEntry {
+							label: "Close All".into(),
+							shortcut: action_keys!(DialogMessageDiscriminant::CloseAllDocumentsWithConfirmation),
+							action: MenuBarEntry::create_action(|_| DialogMessage::CloseAllDocumentsWithConfirmation.into()),
+							disabled: no_active_document,
+							..MenuBarEntry::default()
+						},
+					],
+					vec![MenuBarEntry {
+						label: "Save".into(),
+						shortcut: action_keys!(DocumentMessageDiscriminant::SaveDocument),
+						action: MenuBarEntry::create_action(|_| DocumentMessage::SaveDocument.into()),
+						disabled: no_active_document,
+						..MenuBarEntry::default()
+					}],
+					vec![
+						MenuBarEntry {
+							label: "Import…".into(),
+							shortcut: action_keys!(PortfolioMessageDiscriminant::Import),
+							action: MenuBarEntry::create_action(|_| PortfolioMessage::Import.into()),
+							..MenuBarEntry::default()
+						},
+						MenuBarEntry {
+							label: "Export…".into(),
+							shortcut: action_keys!(DialogMessageDiscriminant::RequestExportDialog),
+							action: MenuBarEntry::create_action(|_| DialogMessage::RequestExportDialog.into()),
+							disabled: no_active_document,
+							..MenuBarEntry::default()
+						},
+					],
+					vec![MenuBarEntry {
+						label: "Preferences…".into(),
+						icon: Some("Settings".into()),
+						shortcut: action_keys!(DialogMessageDiscriminant::RequestPreferencesDialog),
+						action: MenuBarEntry::create_action(|_| DialogMessage::RequestPreferencesDialog.into()),
+						..MenuBarEntry::default()
+					}],
+				]),
+			),
 			MenuBarEntry::new_root(
 				"Help".into(),
+				true,
 				MenuBarEntryChildren(vec![
 					vec![MenuBarEntry {
 						label: "About Graphite".into(),
@@ -327,6 +347,11 @@ impl PropertyHolder for MenuBarMessageHandler {
 					],
 				]),
 			),
-		]))
+		];
+
+		if !no_active_document {
+			menu_bar_entries.splice(2..2, conditional_menu_entries);
+		}
+		Layout::MenuLayout(MenuLayout::new(menu_bar_entries))
 	}
 }
diff --git a/editor/src/messages/portfolio/portfolio_message_handler.rs b/editor/src/messages/portfolio/portfolio_message_handler.rs
index b62c6774..3edb8cba 100644
--- a/editor/src/messages/portfolio/portfolio_message_handler.rs
+++ b/editor/src/messages/portfolio/portfolio_message_handler.rs
@@ -33,11 +33,13 @@ pub struct PortfolioMessageHandler {
 impl MessageHandler<PortfolioMessage, (&InputPreprocessorMessageHandler, &PreferencesMessageHandler)> for PortfolioMessageHandler {
 	#[remain::check]
 	fn process_message(&mut self, message: PortfolioMessage, responses: &mut VecDeque<Message>, (ipp, preferences): (&InputPreprocessorMessageHandler, &PreferencesMessageHandler)) {
+		let has_active_document = self.active_document_id.is_some();
+
 		#[remain::sorted]
 		match message {
 			// Sub-messages
 			#[remain::unsorted]
-			PortfolioMessage::MenuBar(message) => self.menu_bar_message_handler.process_message(message, responses, ()),
+			PortfolioMessage::MenuBar(message) => self.menu_bar_message_handler.process_message(message, responses, has_active_document),
 			#[remain::unsorted]
 			PortfolioMessage::Document(message) => {
 				if let Some(document_id) = self.active_document_id {
@@ -109,6 +111,7 @@ impl MessageHandler<PortfolioMessage, (&InputPreprocessorMessageHandler, &Prefer
 					let hint_data = HintData(vec![HintGroup(vec![])]);
 					responses.add(FrontendMessage::UpdateInputHints { hint_data });
 				}
+
 				// Actually delete the document (delay to delete document is required to let the document and properties panel messages above get processed)
 				responses.add(PortfolioMessage::DeleteDocument { document_id });
 
@@ -179,6 +182,7 @@ impl MessageHandler<PortfolioMessage, (&InputPreprocessorMessageHandler, &Prefer
 
 				if self.document_ids.is_empty() {
 					self.active_document_id = None;
+					responses.add(MenuBarMessage::SendLayout);
 				} else if self.active_document_id.is_some() {
 					let document_id = if document_index == self.document_ids.len() {
 						// If we closed the last document take the one previous (same as last)
@@ -195,6 +199,7 @@ impl MessageHandler<PortfolioMessage, (&InputPreprocessorMessageHandler, &Prefer
 				self.documents.clear();
 				self.document_ids.clear();
 				self.active_document_id = None;
+				responses.add(MenuBarMessage::SendLayout);
 			}
 			PortfolioMessage::FontLoaded {
 				font_family,
@@ -462,7 +467,10 @@ impl MessageHandler<PortfolioMessage, (&InputPreprocessorMessageHandler, &Prefer
 				responses.add(PortfolioMessage::UpdateDocumentWidgets);
 				responses.add(NavigationMessage::TranslateCanvas { delta: (0., 0.).into() });
 			}
-			PortfolioMessage::SetActiveDocument { document_id } => self.active_document_id = Some(document_id),
+			PortfolioMessage::SetActiveDocument { document_id } => {
+				self.active_document_id = Some(document_id);
+				responses.add(MenuBarMessage::SendLayout);
+			}
 			PortfolioMessage::SetImageBlobUrl {
 				document_id,
 				layer_path,
diff --git a/editor/src/messages/tool/tool_messages/fill_tool.rs b/editor/src/messages/tool/tool_messages/fill_tool.rs
index 2f953d33..ab686753 100644
--- a/editor/src/messages/tool/tool_messages/fill_tool.rs
+++ b/editor/src/messages/tool/tool_messages/fill_tool.rs
@@ -7,6 +7,7 @@ use crate::messages::tool::utility_types::{EventToMessageMap, Fsm, ToolActionHan
 use crate::messages::tool::utility_types::{HintData, HintGroup, HintInfo};
 
 use document_legacy::intersection::Quad;
+use document_legacy::layers::layer_layer::CachedOutputData;
 use document_legacy::layers::style::Fill;
 
 use glam::DVec2;
@@ -103,6 +104,17 @@ impl Fsm for FillToolFsmState {
 					let quad = Quad::from_box([mouse_pos - tolerance, mouse_pos + tolerance]);
 
 					if let Some(path) = document.document_legacy.intersects_quad_root(quad, render_data).last() {
+						let is_bitmap = document
+							.document_legacy
+							.layer(path)
+							.ok()
+							.and_then(|layer| layer.as_layer().ok())
+							.map_or(false, |layer| matches!(layer.cached_output_data, CachedOutputData::BlobURL(_) | CachedOutputData::SurfaceId(_)));
+
+						if is_bitmap {
+							return self;
+						}
+
 						let color = match lmb_or_rmb {
 							LeftPointerDown => global_tool_data.primary_color,
 							RightPointerDown => global_tool_data.secondary_color,
diff --git a/editor/src/messages/tool/tool_messages/gradient_tool.rs b/editor/src/messages/tool/tool_messages/gradient_tool.rs
index 613aeeda..efffb9fc 100644
--- a/editor/src/messages/tool/tool_messages/gradient_tool.rs
+++ b/editor/src/messages/tool/tool_messages/gradient_tool.rs
@@ -11,6 +11,7 @@ use crate::messages::tool::utility_types::{HintData, HintGroup, HintInfo};
 
 use document_legacy::intersection::Quad;
 use document_legacy::layers::layer_info::Layer;
+use document_legacy::layers::layer_layer::CachedOutputData;
 use document_legacy::layers::style::{Fill, Gradient, GradientType, PathStyle, RenderData, Stroke};
 use document_legacy::LayerId;
 use document_legacy::Operation;
@@ -420,9 +421,6 @@ impl Fsm for GradientToolFsmState {
 					}
 
 					for path in document.selected_visible_layers() {
-						if !document.document_legacy.multiply_transforms(path).unwrap().inverse().is_finite() {
-							continue;
-						}
 						let layer = document.document_legacy.layer(path).unwrap();
 
 						if let Ok(Fill::Gradient(gradient)) = layer.style().map(|style| style.fill()) {
@@ -568,7 +566,18 @@ impl Fsm for GradientToolFsmState {
 						let quad = Quad::from_box([input.mouse.position - tolerance, input.mouse.position + tolerance]);
 						let intersection = document.document_legacy.intersects_quad_root(quad, render_data).pop();
 
+						// the intersection is the layer where the gradient is being applied
 						if let Some(intersection) = intersection {
+							let is_bitmap = document
+								.document_legacy
+								.layer(&intersection)
+								.ok()
+								.and_then(|layer| layer.as_layer().ok())
+								.map_or(false, |layer| matches!(layer.cached_output_data, CachedOutputData::BlobURL(_) | CachedOutputData::SurfaceId(_)));
+							if is_bitmap {
+								return self;
+							}
+
 							if !document.selected_layers_contains(&intersection) {
 								let replacement_selected_layers = vec![intersection.clone()];
 
diff --git a/frontend/src/components/widgets/inputs/MenuBarInput.svelte b/frontend/src/components/widgets/inputs/MenuBarInput.svelte
index a1dce1f4..7ca66876 100644
--- a/frontend/src/components/widgets/inputs/MenuBarInput.svelte
+++ b/frontend/src/components/widgets/inputs/MenuBarInput.svelte
@@ -63,7 +63,7 @@
 				// New fields in `MenuListEntry`
 				shortcutRequiresLock: entry.shortcut ? shortcutRequiresLock(entry.shortcut.keys) : undefined,
 				value: undefined,
-				disabled: undefined,
+				disabled: entry.disabled ?? undefined,
 				font: undefined,
 				ref: undefined,
 			});
diff --git a/frontend/src/wasm-communication/messages.ts b/frontend/src/wasm-communication/messages.ts
index 81addb4c..7dcdb1fe 100644
--- a/frontend/src/wasm-communication/messages.ts
+++ b/frontend/src/wasm-communication/messages.ts
@@ -774,6 +774,7 @@ type MenuEntryCommon = {
 export type MenuBarEntry = MenuEntryCommon & {
 	action: Widget;
 	children?: MenuBarEntry[][];
+    disabled?: boolean,
 };
 
 // An entry in the all-encompassing MenuList component which defines all types of menus ranging from `MenuBarInput` to `DropdownInput` widgets
@@ -1300,6 +1301,7 @@ function createMenuLayoutRecursive(children: any[][]): MenuBarEntry[][] {
 			...entry,
 			action: hoistWidgetHolders([entry.action])[0],
 			children: entry.children ? createMenuLayoutRecursive(entry.children) : undefined,
+            disabled: entry.disabled ?? false,
 		}))
 	);
 }