diff --git a/scripts/macros/rollDice.mjs b/scripts/macros/rollDice.mjs
index c4011eb..b6bebf9 100644
--- a/scripts/macros/rollDice.mjs
+++ b/scripts/macros/rollDice.mjs
@@ -1,17 +1,29 @@
 async function rollDice() {
-
-	const statBase = await DialogManager.ask({
-		question: `How many dice to roll?`,
-		initialValue: 2,
-		inputType: `number`,
-	});
-
-	if (!statBase) {
-		return;
-	}
-
 	const sidesOnDice = 6;
-	const successThreshold = 4;
+
+	const answers = await DialogManager.ask({
+		id: `eat-the-reich-dice-pool`,
+		question: `Set up your dice pool:`,
+		inputs: [
+			{
+				inputType: `number`,
+				defaultValue: 2,
+				label: `Number of Dice`,
+				autofocus: true,
+			},
+			{
+				inputType: `number`,
+				defaultValue: 4,
+				label: `Success Threshold (d${sidesOnDice} >= X)`,
+			},
+			{
+				inputType: `checkbox`,
+				defaultValue: true,
+				label: `Enable Criticals`,
+			},
+		],
+	});
+	const [ statBase, successThreshold, critsEnabled ] = Object.values(answers);
 
 	let successes = 0;
 	const results = [];
@@ -22,14 +34,17 @@ async function rollDice() {
 		if (r.total >= successThreshold) {
 			successes++;
 		}
-		if (r.total === sidesOnDice) {
+		if (r.total === sidesOnDice && critsEnabled) {
 			successes++;
 		}
 	}
 
-	await ChatMessage.create({
+	const m = new ChatMessage({
+		title: `Dice Pool`,
 		content: `Rolled: ${results.join(`, `)}<br>Successes: ${successes}`,
 	});
+	m.applyRollMode(game.settings.get(`core`, `rollMode`));
+	ui.chat.postOne(m);
 }
 
 rollDice()
\ No newline at end of file
diff --git a/src/utils/DialogManager.mjs b/src/utils/DialogManager.mjs
index 56d1d9b..5dae6c8 100644
--- a/src/utils/DialogManager.mjs
+++ b/src/utils/DialogManager.mjs
@@ -79,49 +79,89 @@ export class DialogManager {
 	/**
 	 * Asks the user to provide a simple piece of information, this is primarily
 	 * intended to be used within macros so that it can have better info gathering
-	 * as needed.
+	 * as needed. This returns an object of input labels to the value the user
+	 * input for that label, if there is only one input, this will return the value
+	 * without an object wrapper, allowing for easier access.
 	 */
 	static async ask(data, opts = {}) {
-		if (!data.question) {
-			throw new Error(`Asking the user for input must contain a question`);
+		if (!data.id) {
+			throw new Error(`Asking the user for input must contain an ID`);
+		}
+		if (!data.inputs.length) {
+			throw new Error(`Must include at least one input specification when prompting the user`);
 		}
-		data.inputType ??= `text`;
-		data.initialValue ??= ``;
 
-		opts.title ??= `System Question`;
+		let autofocusClaimed = false;
+		for (const i of data.inputs) {
+			i.id ??= foundry.utils.randomID(16);
+			i.inputType ??= `text`;
+
+			// Only ever allow one input to claim autofocus
+			i.autofocus &&= !autofocusClaimed;
+			autofocusClaimed ||= i.autofocus;
+
+			// Set the value's attribute name if it isn't specified explicitly
+			if (!i.valueAttribute) {
+				switch (i.inputType) {
+					case `checkbox`:
+						i.valueAttribute = `checked`;
+						break;
+					default:
+						i.valueAttribute = `value`;
+				};
+			};
+		};
+
 		opts.jQuery = true;
+		data.default ??= `confirm`;
+		data.title ??= `System Question`;
 
-		const content = await renderTemplate(
+		data.content = await renderTemplate(
 			`systems/${game.system.id}/templates/Dialogs/ask.hbs`,
 			data,
 		);
 
 		return new Promise((resolve, reject) => {
 			DialogManager.createOrFocus(
-				data.question,
+				data.id,
 				{
-					content,
+					...data,
 					buttons: {
 						confirm: {
 							label: `Confirm`,
 							callback: (html) => {
-								const element = html.find(`.user-input`)[0];
-								let value = element.value;
-								switch (data.inputType) {
-									case `number`:
-										value = parseFloat(value);
-										break;
-									case `checkbox`:
-										value = element.checked;
-										break;
+								const answers = {};
+
+								/*
+								Retrieve the answer for every input provided using the ID
+								determined during initial data prep, and assign the value
+								to the property of the label in the object.
+								*/
+								for (const i of data.inputs) {
+									const element = html.find(`#${i.id}`)[0];
+									let value = element.value;
+									switch (i.inputType) {
+										case `number`:
+											value = parseFloat(value);
+											break;
+										case `checkbox`:
+											value = element.checked;
+											break;
+									}
+									Logger.debug(`Ask response: ${value} (type: ${typeof value})`);
+									answers[i.label] = value;
+									if (data.inputs.length === 1) {
+										resolve(value);
+										return;
+									}
 								}
-								Logger.debug(`Ask response: ${value} (type: ${typeof value})`);
-								resolve(value);
+
+								resolve(answers);
 							},
 						},
 						cancel: {
 							label: `Cancel`,
-							callback: () => reject(),
+							callback: () => reject(`User cancelled the prompt`),
 						},
 					},
 				},
diff --git a/styles/v1/Dialog.scss b/styles/v1/Dialog.scss
index 9522789..28f133f 100644
--- a/styles/v1/Dialog.scss
+++ b/styles/v1/Dialog.scss
@@ -1,3 +1,12 @@
 .dialog-content:not(:only-child) {
 	margin-bottom: 8px;
 }
+
+.dialog-content {
+	p {
+		margin: 0;
+	}
+	.prompt {
+		margin-top: 8px;
+	}
+}
diff --git a/system.json b/system.json
index e9fde47..bf0ff7c 100644
--- a/system.json
+++ b/system.json
@@ -2,7 +2,7 @@
 	"id": "taf",
 	"title": "Text-Based Actors",
 	"description": "",
-	"version": "1.0.0",
+	"version": "1.1.0",
 	"download": "https://github.com/Oliver-Akins/Text-Actors-Foundry/releases/latest/download/dotdungeon.zip",
 	"manifest": "https://github.com/Oliver-Akins/Text-Actors-Foundry/releases/latest/download/system.json",
 	"url": "https://github.com/Oliver-Akins/Text-Actors-Foundry",
diff --git a/templates/Dialogs/ask.hbs b/templates/Dialogs/ask.hbs
index d08d8a2..a37f56e 100644
--- a/templates/Dialogs/ask.hbs
+++ b/templates/Dialogs/ask.hbs
@@ -1,12 +1,27 @@
-<div>
+<div class="ask-dialog">
 	<p>
-		{{question}}
+		{{ question }}
 	</p>
-	<input
-		type="{{inputType}}"
-		value="{{initialValue}}"
-		checked="{{initialValue}}"
-		class="user-input"
-		autofocus
-	>
+	{{#each inputs as | i | }}
+		<div class="prompt">
+			<label
+				for="{{i.id}}"
+				class="prompt__label"
+			>
+				{{ i.label }}
+			</label>
+			<input
+				type="{{i.inputType}}"
+				id="{{i.id}}"
+				class="patrons__input"
+				{{i.valueAttribute}}="{{i.defaultValue}}"
+				{{#if i.autofocus}}autofocus{{/if}}
+			>
+			{{#if i.details}}
+				<p class="prompt__details">
+					{{{ i.details }}}
+				</p>
+			{{/if}}
+		</div>
+	{{/each}}
 </div>