diff --git a/client/web/src/components/widgets/buttons/IconButton.vue b/client/web/src/components/widgets/buttons/IconButton.vue
index d2dec1077..6fdacfa88 100644
--- a/client/web/src/components/widgets/buttons/IconButton.vue
+++ b/client/web/src/components/widgets/buttons/IconButton.vue
@@ -1,5 +1,5 @@
 <template>
-	<button class="icon-button" :class="`size-${String(size)}`">
+	<button class="icon-button" :class="`size-${String(size)}`" @click="onClick">
 		<IconLabel :icon="icon" />
 	</button>
 </template>
@@ -60,6 +60,7 @@ export default defineComponent({
 		icon: { type: String, required: true },
 		size: { type: Number, required: true },
 		gapAfter: { type: Boolean, default: false },
+		onClick: Function,
 	},
 	components: { IconLabel },
 });
diff --git a/client/web/src/components/widgets/options/ToolOptions.vue b/client/web/src/components/widgets/options/ToolOptions.vue
index 87d647811..f4aafdb66 100644
--- a/client/web/src/components/widgets/options/ToolOptions.vue
+++ b/client/web/src/components/widgets/options/ToolOptions.vue
@@ -1,7 +1,7 @@
 <template>
 	<div class="tool-options">
 		<template v-for="(option, index) in optionsMap.get(activeTool) || []" :key="index">
-			<IconButton v-if="option.kind === 'icon_button'" :icon="option.icon" :size="24" :title="option.title" />
+			<IconButton v-if="option.kind === 'icon_button'" :icon="option.icon" :size="24" :title="option.title" :onClick="() => sendToolMessage(option.message)" />
 			<Separator v-if="option.kind === 'separator'" :type="option.type" />
 			<PopoverButton v-if="option.kind === 'popover_button'">
 				<h3>{{ option.title }}</h3>
@@ -38,6 +38,7 @@ interface IconButtonOption {
 	kind: "icon_button";
 	icon: string;
 	title: string;
+	message?: string;
 }
 
 interface SeparatorOption {
@@ -74,6 +75,12 @@ export default defineComponent({
 			// This is a placeholder call, using the Shape tool as an example
 			set_tool_options(this.$props.activeTool || "", { Shape: { shape_type: { Polygon: { vertices: newValue } } } });
 		},
+		async sendToolMessage(message?: string) {
+			if (message) {
+				const { send_tool_message } = await wasm;
+				send_tool_message(this.$props.activeTool || "", message);
+			}
+		},
 	},
 	data() {
 		const optionsMap: ToolOptionsMap = new Map([
@@ -96,8 +103,8 @@ export default defineComponent({
 
 					{ kind: "separator", type: SeparatorType.Section },
 
-					{ kind: "icon_button", icon: "FlipHorizontal", title: "Flip Horizontal" },
-					{ kind: "icon_button", icon: "FlipVertical", title: "Flip Vertical" },
+					{ kind: "icon_button", icon: "FlipHorizontal", title: "Flip Horizontal", message: "FlipHorizontal" },
+					{ kind: "icon_button", icon: "FlipVertical", title: "Flip Vertical", message: "FlipVertical" },
 
 					{ kind: "separator", type: SeparatorType.Related },
 
diff --git a/client/web/wasm/src/document.rs b/client/web/wasm/src/document.rs
index dc62ccc92..4627aa7aa 100644
--- a/client/web/wasm/src/document.rs
+++ b/client/web/wasm/src/document.rs
@@ -4,7 +4,7 @@ use crate::EDITOR_STATE;
 use editor_core::input::input_preprocessor::ModifierKeys;
 use editor_core::input::mouse::ScrollDelta;
 use editor_core::message_prelude::*;
-use editor_core::tool::tool_options::ToolOptions;
+use editor_core::tool::{tool_options::ToolOptions, tools, ToolType};
 use editor_core::{
 	input::mouse::{MouseState, ViewportPosition},
 	LayerId,
@@ -30,12 +30,31 @@ pub fn set_tool_options(tool: String, options: &JsValue) -> Result<(), JsValue>
 	match options.into_serde::<ToolOptions>() {
 		Ok(options) => EDITOR_STATE.with(|editor| match translate_tool(&tool) {
 			Some(tool) => editor.borrow_mut().handle_message(ToolMessage::SetToolOptions(tool, options)).map_err(convert_error),
-			None => Err(Error::new(&format!("Couldn't select {} because it was not recognized as a valid tool", tool)).into()),
+			None => Err(Error::new(&format!("Couldn't set options for {} because it was not recognized as a valid tool", tool)).into()),
 		}),
-		Err(err) => Err(Error::new(&format!("Invalud JSON for ToolOptions: {}", err)).into()),
+		Err(err) => Err(Error::new(&format!("Invalid JSON for ToolOptions: {}", err)).into()),
 	}
 }
 
+/// Send a message to a given tool
+#[wasm_bindgen]
+pub fn send_tool_message(tool: String, message: &JsValue) -> Result<(), JsValue> {
+	let tool_message = match translate_tool(&tool) {
+		Some(tool) => match tool {
+			ToolType::Select => match message.into_serde::<tools::select::SelectMessage>() {
+				Ok(select_message) => Ok(ToolMessage::Select(select_message)),
+				Err(err) => Err(Error::new(&format!("Invalid message for {}: {}", tool, err)).into()),
+			},
+			_ => Err(Error::new(&format!("Tool message sending not implemented for {}", tool)).into()),
+		},
+		None => Err(Error::new(&format!("Couldn't send message for {} because it was not recognized as a valid tool", tool)).into()),
+	};
+	EDITOR_STATE.with(|editor| match tool_message {
+		Ok(tool_message) => editor.borrow_mut().handle_message(tool_message).map_err(convert_error),
+		Err(err) => Err(err),
+	})
+}
+
 #[wasm_bindgen]
 pub fn select_document(document: usize) -> Result<(), JsValue> {
 	EDITOR_STATE.with(|editor| editor.borrow_mut().handle_message(DocumentMessage::SelectDocument(document)).map_err(convert_error))
diff --git a/core/editor/src/document/document_message_handler.rs b/core/editor/src/document/document_message_handler.rs
index 62342b282..9138cae23 100644
--- a/core/editor/src/document/document_message_handler.rs
+++ b/core/editor/src/document/document_message_handler.rs
@@ -5,7 +5,7 @@ use crate::{
 };
 use document_core::layers::Layer;
 use document_core::{DocumentResponse, LayerId, Operation as DocumentOperation};
-use glam::DAffine2;
+use glam::{DAffine2, DVec2};
 use log::warn;
 
 use crate::document::Document;
@@ -55,6 +55,7 @@ pub enum DocumentMessage {
 	SetCanvasRotation(f64),
 	NudgeSelectedLayers(f64, f64),
 	ReorderSelectedLayers(i32),
+	FlipLayer(Vec<LayerId>, bool, bool),
 }
 
 impl From<DocumentOperation> for DocumentMessage {
@@ -594,6 +595,18 @@ impl MessageHandler<DocumentMessage, &InputPreprocessor> for DocumentMessageHand
 					responses.push_back(DocumentMessage::SelectLayers(selected_layer_paths).into());
 				}
 			}
+			FlipLayer(path, flip_horizontal, flip_vertical) => {
+				if let Ok(layer) = self.active_document_mut().document.layer_mut(&path) {
+					let scale = DVec2::new(if flip_horizontal { -1. } else { 1. }, if flip_vertical { -1. } else { 1. });
+					responses.push_back(
+						DocumentOperation::SetLayerTransform {
+							path,
+							transform: (layer.transform * DAffine2::from_scale(scale)).to_cols_array(),
+						}
+						.into(),
+					);
+				}
+			}
 			message => todo!("document_action_handler does not implement: {}", message.to_discriminant().global_name()),
 		}
 	}
diff --git a/core/editor/src/tool/tools/select.rs b/core/editor/src/tool/tools/select.rs
index 55f908977..590298d4f 100644
--- a/core/editor/src/tool/tools/select.rs
+++ b/core/editor/src/tool/tools/select.rs
@@ -4,6 +4,7 @@ use document_core::layers::style::Fill;
 use document_core::layers::style::Stroke;
 use document_core::Operation;
 use glam::{DAffine2, DVec2};
+use serde::{Deserialize, Serialize};
 
 use crate::input::{mouse::ViewportPosition, InputPreprocessor};
 use crate::tool::{DocumentToolData, Fsm, ToolActionHandlerData};
@@ -16,12 +17,15 @@ pub struct Select {
 }
 
 #[impl_message(Message, ToolMessage, Select)]
-#[derive(PartialEq, Clone, Debug)]
+#[derive(PartialEq, Clone, Debug, Serialize, Deserialize)]
 pub enum SelectMessage {
 	DragStart,
 	DragStop,
 	MouseMove,
 	Abort,
+
+	FlipHorizontal,
+	FlipVertical,
 }
 
 impl<'a> MessageHandler<ToolMessage, ToolActionHandlerData<'a>> for Select {
@@ -121,6 +125,22 @@ impl Fsm for SelectToolFsmState {
 
 					Ready
 				}
+				(_, FlipHorizontal) => {
+					let selected_layers = document.layer_data.iter().filter_map(|(path, data)| data.selected.then(|| path.clone()));
+					for path in selected_layers {
+						responses.push_back(DocumentMessage::FlipLayer(path, true, false).into());
+					}
+
+					self
+				}
+				(_, FlipVertical) => {
+					let selected_layers = document.layer_data.iter().filter_map(|(path, data)| data.selected.then(|| path.clone()));
+					for path in selected_layers {
+						responses.push_back(DocumentMessage::FlipLayer(path, false, true).into());
+					}
+
+					self
+				}
 				_ => self,
 			}
 		} else {