diff --git a/apps/web/src/chat/chat.tsx b/apps/web/src/chat/chat.tsx
index 643eff17a..f16cc424a 100644
--- a/apps/web/src/chat/chat.tsx
+++ b/apps/web/src/chat/chat.tsx
@@ -698,8 +698,8 @@ export function Chat(
 						id={cueId}
 					>
 						{sendError
-							? <WarningIcon className="icon-danger" size={14} />
-							: <InfoIcon size={14} />}
+							? <WarningIcon className="icon-danger icon-first-line" size={14} />
+							: <InfoIcon className="icon-first-line" size={14} />}
 						<span>
 							{sendError ?? (researchBlock
 								? researchCopy[researchBlock]
diff --git a/apps/web/src/chat/work-progress.tsx b/apps/web/src/chat/work-progress.tsx
index ae7834ed8..f1dafa66e 100644
--- a/apps/web/src/chat/work-progress.tsx
+++ b/apps/web/src/chat/work-progress.tsx
@@ -47,7 +47,11 @@ function ToolCall(
 	let row = (
 		<>
 			{hasDetails && (
-				<ChevronIcon aria-hidden="true" className={open ? "rotate-90" : ""} size={14} />
+				<ChevronIcon
+					aria-hidden="true"
+					className={open ? "icon-first-line rotate-90" : "icon-first-line"}
+					size={14}
+				/>
 			)}
 			<span className="min-w-0 flex-1 break-words font-mono text-text-secondary">
 				{toolCopy(tool.name)}
diff --git a/apps/web/src/icon-assets.test.ts b/apps/web/src/icon-assets.test.ts
index 32e429cd6..1af1c7769 100644
--- a/apps/web/src/icon-assets.test.ts
+++ b/apps/web/src/icon-assets.test.ts
@@ -181,3 +181,10 @@ test("directional controls reuse one chevron and one panel icon", () => {
 	expect(existsSync(join(root, "assets/icons/tool-chevron-right.svg"))).toBe(false);
 	expect(existsSync(join(root, "assets/figma/navigation/sidebar-right-3-hide.svg"))).toBe(false);
 });
+
+test("icons never shrink beside wrapping text", () => {
+	let css = readFileSync(join(root, "theme.css"), "utf8");
+	expect(css).toMatch(
+		/@layer base \{\s*:is\(\[data-nucleo-icon\], \[data-filled-icon\]\) \{\s*flex-shrink: 0;/,
+	);
+});
diff --git a/apps/web/src/theme.css b/apps/web/src/theme.css
index abdbb46b2..f3b0d4076 100644
--- a/apps/web/src/theme.css
+++ b/apps/web/src/theme.css
@@ -11,6 +11,7 @@
  * `.ts` is included because shared class lists can live outside components.
  */
 @source "../../../packages/editor/src/**/*.{ts,tsx}";
+@source "../../../packages/icons/src/**/*.{ts,tsx}";
 @source "../../../packages/question/src/**/*.{ts,tsx}";
 
 @utility ring-hairline {
@@ -22,6 +23,22 @@
 	color: var(--color-icon);
 }
 
+/*
+ * Every icon keeps its declared size: as a flex item it would otherwise shrink
+ * when the text beside it wraps. In the base layer so a utility can still opt out.
+ */
+@layer base {
+	:is([data-nucleo-icon], [data-filled-icon]) {
+		flex-shrink: 0;
+	}
+}
+
+/* Beside text that may wrap: centre on the first line instead of the whole block. */
+@utility icon-first-line {
+	align-self: flex-start;
+	translate: 0 calc(0.5lh - 50%);
+}
+
 @utility icon-danger {
 	--color-icon: var(--color-danger-icon);
 }
diff --git a/bun.lock b/bun.lock
index 404356379..07e2558cf 100644
--- a/bun.lock
+++ b/bun.lock
@@ -185,6 +185,9 @@
       "devDependencies": {
         "@types/bun": "catalog:bun",
         "@types/react": "catalog:react",
+        "@types/react-dom": "catalog:react",
+        "react": "catalog:react",
+        "react-dom": "catalog:react",
       },
       "peerDependencies": {
         "react": "catalog:react",
diff --git a/e2e/icon-size.e2e.ts b/e2e/icon-size.e2e.ts
new file mode 100644
index 000000000..82d07f258
--- /dev/null
+++ b/e2e/icon-size.e2e.ts
@@ -0,0 +1,116 @@
+/**
+ * Icons keep their declared size beside text that wraps.
+ *
+ * Each icon is a flex item; without `flex-shrink: 0` a long label squeezes it
+ * narrower than its height. Layout is browser behaviour, so this measures every
+ * visible icon on the surfaces where labels wrap, at phone width.
+ */
+
+import { content, expect, test } from "./room";
+import { CHOSEN, SETTLED_ANSWER, SOURCE, STATE } from "./source/icon-size.fixture";
+
+import type { Locator, Page } from "@playwright/test";
+
+/** Icons whose rendered box differs from the size they were declared at. */
+function squeezed(scope: Locator) {
+	return scope.evaluateAll(roots =>
+		roots.flatMap(root =>
+			[...root.querySelectorAll("svg[width]")].flatMap(icon => {
+				let box = icon.getBoundingClientRect();
+				if (box.width === 0 && box.height === 0) return [];
+				let size = Number(icon.getAttribute("width"));
+				return Math.abs(box.width - size) > 0.5 || Math.abs(box.height - size) > 0.5
+					? [
+						`${box.width.toFixed(1)}×${box.height.toFixed(1)}, declared ${size}: ${
+							root.textContent?.slice(0, 60)
+						}`,
+					]
+					: [];
+			})
+		)
+	);
+}
+
+/** How far an icon's centre sits from the centre of its row's first text line. */
+function firstLineOffset(row: Locator) {
+	return row.evaluate(element => {
+		let icon = element.querySelector("svg")!.getBoundingClientRect();
+		let top = element.getBoundingClientRect().top;
+		let line = Number.parseFloat(getComputedStyle(element).lineHeight);
+		return Math.abs(icon.top + icon.height / 2 - (top + line / 2));
+	});
+}
+
+async function phone(page: Page) {
+	await page.setViewportSize({ width: 390, height: 844 });
+}
+
+test("icons keep their size and sit on the first line beside wrapped decision text", async ({ join, seed }) => {
+	await seed(SOURCE, STATE);
+	let page = await join("ana");
+	await phone(page);
+
+	let settled = content(page).locator("[data-card-settled]");
+	await expect(settled).toContainText(SETTLED_ANSWER);
+	expect((await settled.boundingBox())!.height).toBeGreaterThan(30);
+	expect(await squeezed(settled)).toEqual([]);
+	expect(await firstLineOffset(settled)).toBeLessThan(1.5);
+
+	await page.getByRole("button", { name: `Decision: ${CHOSEN}` }).click();
+	let dialog = page.getByRole("dialog", { name: "Decision" });
+	await expect(dialog).toContainText("Phased over a whole quarter");
+	let answers = dialog.locator(".plan-decision-answer");
+	await expect(answers).toHaveCount(3);
+	expect(await squeezed(dialog)).toEqual([]);
+	for (let answer of await answers.all()) {
+		expect(await firstLineOffset(answer)).toBeLessThan(1.5);
+	}
+	await page.keyboard.press("Escape");
+	await expect(dialog).toHaveCount(0);
+
+	await page.getByRole("button", { name: /^Decisions/ }).click();
+	let decisions = page.locator('[data-document-view="decisions"]');
+	await decisions.getByRole("button", { name: /resolved/ }).click();
+	await expect(decisions).toContainText("How should we roll this out?");
+	await expect.poll(() => squeezed(decisions)).toEqual([]);
+});
+
+test("header, menu, Chat and sidebar icons keep their size when every row wraps", async ({ join, seed }) => {
+	await seed(SOURCE, STATE);
+	let page = await join("ana");
+	await phone(page);
+
+	// Squeeze every row the way a long title or label would.
+	let narrow = (scope: Locator) =>
+		scope.evaluateAll(roots => {
+			for (let root of roots) {
+				for (let icon of root.querySelectorAll("svg[width]")) {
+					let row = icon.parentElement;
+					if (row && getComputedStyle(row).display.includes("flex")) row.style.maxWidth = "2.5rem";
+				}
+			}
+		});
+
+	let header = page.getByRole("banner");
+	await narrow(header);
+	await expect.poll(() => squeezed(header)).toEqual([]);
+
+	await page.getByRole("button", { name: /^Actions for / }).click();
+	let menu = page.getByRole("menu");
+	await expect(menu).toBeVisible();
+	await narrow(menu);
+	await expect.poll(() => squeezed(menu)).toEqual([]);
+	await page.keyboard.press("Escape");
+
+	await page.getByRole("button", { name: "Chat", exact: true }).click();
+	let chat = page.getByRole("complementary", { name: "Chat" });
+	await expect(chat.getByRole("combobox", { name: "Message" })).toBeVisible();
+	await narrow(chat);
+	await expect.poll(() => squeezed(chat)).toEqual([]);
+
+	await page.getByRole("button", { name: "Show sidebar" }).click();
+	let sidebar = page.getByRole("navigation", { name: /project|sidebar|documents/i });
+	await expect(sidebar.first()).toBeVisible();
+	await narrow(sidebar);
+	await expect.poll(() => squeezed(sidebar)).toEqual([]);
+});
diff --git a/e2e/source/icon-size.fixture.ts b/e2e/source/icon-size.fixture.ts
new file mode 100644
index 000000000..ff57d7622
--- /dev/null
+++ b/e2e/source/icon-size.fixture.ts
@@ -0,0 +1,103 @@
+/** A document whose decisions carry option labels long enough to wrap beside their icons. */
+
+import { createHash } from "node:crypto";
+
+export const PROSE = "The rollout goes team by team, starting with the documentation team.";
+export const RESOLVED = "01K0N4TR8K7JGM4R1J7PW4R8YJ";
+export const SETTLED = "01K0N4TR8K7JGM4R1J7PW4R8YK";
+const RESOLVED_QUESTION = "01K0N4V4E7Y6P4MJ5WD8XZF3B2";
+const SETTLED_QUESTION = "01K0N4V4E7Y6P4MJ5WD8XZF3B3";
+const AT = "2026-09-23T15:13:00.000Z";
+
+export const CHOSEN =
+	"Team by team, starting with the documentation team and widening after a review";
+const LABELS = [
+	"All at once",
+	CHOSEN,
+	"Phased over a whole quarter with an opt-in beta for the teams who ask first",
+];
+export const SETTLED_ANSWER =
+	"Keep room state on disk as canonical MDX beside the transcript and its sidecar";
+
+function digest(text: string): string {
+	return `sha256:${createHash("sha256").update(`${text}\n`).digest("hex")}`;
+}
+
+function optionId(question: string, index: number): string {
+	return `${question.slice(0, 22)}${question.slice(-2)}0${index}`;
+}
+
+function definition(question: string, prompt: string, labels: string[]) {
+	return {
+		questions: [{
+			id: question,
+			header: "Rollout",
+			question: prompt,
+			multiple: false,
+			options: labels.map((label, index) => ({
+				id: optionId(question, index),
+				label,
+				description: "",
+			})),
+		}],
+	};
+}
+
+const RESOLVED_CARD = `<Questionnaire id="${RESOLVED}" by="ana" at="${AT}">
+<Question id="${RESOLVED_QUESTION}" header="Rollout" prompt="How should we roll this out?" multiple="false">
+${
+	LABELS.map((label, index) =>
+		`<Option id="${optionId(RESOLVED_QUESTION, index)}" label="${label}" />`
+	).join("\n")
+}
+<Answer value="${CHOSEN}" />
+</Question>
+</Questionnaire>`;
+
+const SETTLED_CARD = `<Questionnaire id="${SETTLED}" by="ana" status="decided">
+<Question id="${SETTLED_QUESTION}" header="Storage" prompt="Where should room state live?" multiple="false">
+<Option id="${optionId(SETTLED_QUESTION, 0)}" label="${SETTLED_ANSWER}" />
+<Answer value="${SETTLED_ANSWER}" choices="${optionId(SETTLED_QUESTION, 0)}" />
+</Question>
+</Questionnaire>`;
+
+export const SOURCE = `${PROSE}\n\n${RESOLVED_CARD}\n\n${SETTLED_CARD}\n\n${
+	"Padding paragraph.\n\n".repeat(20)
+}`;
+
+export const STATE = {
+	revision: 1,
+	questions: [
+		{
+			id: RESOLVED,
+			status: "answered",
+			definition: definition(RESOLVED_QUESTION, "How should we roll this out?", LABELS),
+			answers: { [RESOLVED_QUESTION]: CHOSEN },
+			resolver: "ana",
+			at: Date.parse(AT) / 1_000,
+			anchors: {
+				widget: RESOLVED,
+				questions: {
+					[RESOLVED_QUESTION]: {
+						anchors: [{ epoch: "stale", position: "", digest: digest(PROSE) }],
+						pending: false,
+					},
+				},
+			},
+		},
+		{
+			id: SETTLED,
+			definition: definition(SETTLED_QUESTION, "Where should room state live?", [SETTLED_ANSWER]),
+			status: "answered",
+			answers: { [SETTLED_QUESTION]: SETTLED_ANSWER },
+			choices: [optionId(SETTLED_QUESTION, 0)],
+			resolver: "ana",
+			owner: "ana",
+			decidedAt: 1_790_000_000,
+			history: [],
+			optionOrigins: {},
+			editors: [],
+			origin: "conversation",
+		},
+	],
+};
diff --git a/packages/editor/src/resolved-layer.tsx b/packages/editor/src/resolved-layer.tsx
index 95c6f58ab..7d94e45b2 100644
--- a/packages/editor/src/resolved-layer.tsx
+++ b/packages/editor/src/resolved-layer.tsx
@@ -181,7 +181,7 @@ function Popover(
 				</span>
 			</div>
 			<p className="plan-decision-answer">
-				<CheckIcon aria-hidden="true" />
+				<CheckIcon aria-hidden="true" className="icon-first-line" />
 				<span>{decision.answer}</span>
 			</p>
 			{others.length > 0 && (
@@ -189,7 +189,7 @@ function Popover(
 					<div>
 						{others.map(label => (
 							<p className="plan-decision-answer" data-rejected="" key={label}>
-								<CloseIcon aria-hidden="true" />
+								<CloseIcon aria-hidden="true" className="icon-first-line" />
 								<span>{label}</span>
 							</p>
 						))}
@@ -209,7 +209,7 @@ function Popover(
 					)}
 					{decision.at && when(decision.at) && (
 						<p>
-							<ClockIcon aria-hidden="true" />
+							<ClockIcon aria-hidden="true" className="icon-first-line" />
 							<span>{when(decision.at)}</span>
 						</p>
 					)}
diff --git a/packages/editor/src/styles.css b/packages/editor/src/styles.css
index 0d3072c8e..01ebc70c5 100644
--- a/packages/editor/src/styles.css
+++ b/packages/editor/src/styles.css
@@ -3367,10 +3367,6 @@
 	flex: none;
 }
 
-.plan-decision-meta > p > svg {
-	margin-block: calc((1lh - 0.875rem) / 2);
-}
-
 .plan-decision-meta > p > :is(img, [role="img"]) {
 	margin-block: calc((1lh - 1.125rem) / 2);
 }
diff --git a/packages/editor/src/widgets/questionnaire.tsx b/packages/editor/src/widgets/questionnaire.tsx
index bdade54b3..b2b4b4f8d 100644
--- a/packages/editor/src/widgets/questionnaire.tsx
+++ b/packages/editor/src/widgets/questionnaire.tsx
@@ -444,7 +444,7 @@ function SettledLine(
 			data-card-settled=""
 			data-plan-sidecar-questionnaire={value.id}
 		>
-			<DecisionIcon aria-hidden="true" size={14} />
+			<DecisionIcon aria-hidden="true" className="icon-first-line" size={14} />
 			<span>
 				Decided: {chosen.length ? chosen.join(", ") : "Saved decision"}
 				{owner ? ` · @${owner}` : ""}
diff --git a/packages/icons/package.json b/packages/icons/package.json
index c11775f42..2a36677d8 100644
--- a/packages/icons/package.json
+++ b/packages/icons/package.json
@@ -17,6 +17,9 @@
 	},
 	"devDependencies": {
 		"@types/bun": "catalog:bun",
-		"@types/react": "catalog:react"
+		"@types/react": "catalog:react",
+		"@types/react-dom": "catalog:react",
+		"react": "catalog:react",
+		"react-dom": "catalog:react"
 	}
 }
diff --git a/packages/icons/src/brand.tsx b/packages/icons/src/brand.tsx
index 685d8b0ab..b9eb14aa5 100644
--- a/packages/icons/src/brand.tsx
+++ b/packages/icons/src/brand.tsx
@@ -1,6 +1,13 @@
 export function GitHubIcon({ size = 16 }: { size?: number }) {
 	return (
-		<svg aria-hidden="true" fill="currentColor" height={size} viewBox="0 0 16 16" width={size}>
+		<svg
+			aria-hidden="true"
+			data-filled-icon=""
+			fill="currentColor"
+			height={size}
+			viewBox="0 0 16 16"
+			width={size}
+		>
 			<path d="M8 0C3.58 0 0 3.58 0 8c0 3.54 2.29 6.53 5.47 7.59.4.07.55-.17.55-.38 0-.19-.01-.82-.01-1.49-2.01.37-2.53-.49-2.69-.94-.09-.23-.48-.94-.82-1.13-.28-.15-.68-.52-.01-.53.63-.01 1.08.58 1.23.82.72 1.21 1.87.87 2.33.66.07-.52.28-.87.51-1.07-1.78-.2-3.64-.89-3.64-3.95 0-.87.31-1.59.82-2.15-.08-.2-.36-1.02.08-2.12 0 0 .67-.21 2.2.82.64-.18 1.32-.27 2-.27s1.36.09 2 .27c1.53-1.04 2.2-.82 2.2-.82.44 1.1.16 1.92.08 2.12.51.56.82 1.27.82 2.15 0 3.07-1.87 3.75-3.65 3.95.29.25.54.73.54 1.48 0 1.07-.01 1.93-.01 2.2 0 .21.15.46.55.38A8.01 8.01 0 0 0 16 8c0-4.42-3.58-8-8-8Z" />
 		</svg>
 	);
diff --git a/packages/icons/src/filled.tsx b/packages/icons/src/filled.tsx
index 4172e5fb7..f615ace35 100644
--- a/packages/icons/src/filled.tsx
+++ b/packages/icons/src/filled.tsx
@@ -5,6 +5,7 @@ export function ChopinIcon({ size = 14, ...props }: IconProps) {
 	return (
 		<svg
 			aria-hidden={labelled ? undefined : true}
+			data-filled-icon=""
 			height={size}
 			viewBox="0 0 18 18"
 			width={size}
diff --git a/packages/icons/src/icon.test.tsx b/packages/icons/src/icon.test.tsx
new file mode 100644
index 000000000..2599709a3
--- /dev/null
+++ b/packages/icons/src/icon.test.tsx
@@ -0,0 +1,12 @@
+import { expect, test } from "bun:test";
+import { renderToStaticMarkup } from "react-dom/server";
+
+import * as icons from "./index";
+
+// The web stylesheet holds these markers at their declared size (`flex-shrink: 0`).
+test("every icon carries a marker that keeps it from shrinking beside wrapping text", () => {
+	for (let [name, Icon] of Object.entries(icons)) {
+		let html = renderToStaticMarkup(<Icon />);
+		expect(html, name).toMatch(/^<svg[^>]* data-(nucleo|filled)-icon=""/);
+	}
+});
diff --git a/scripts/design-contract/exceptions/dynamic-editor.json b/scripts/design-contract/exceptions/dynamic-editor.json
index f9f676669..67aea35aa 100644
--- a/scripts/design-contract/exceptions/dynamic-editor.json
+++ b/scripts/design-contract/exceptions/dynamic-editor.json
@@ -403,7 +403,7 @@
 				1
 			]
 		],
-		"sourceHash": "d1d4af2207bbd028118c9a2869c15073c18bb46d41967111fb9be57b1a1947f7"
+		"sourceHash": "49ccb021fb60c45cdbe234241549e468ba556277d74d824145ca8707ff2bc908"
 	},
 	{
 		"file": "packages/editor/src/widgets/code-view.tsx",
@@ -466,7 +466,7 @@
 				1
 			]
 		],
-		"sourceHash": "d1d4af2207bbd028118c9a2869c15073c18bb46d41967111fb9be57b1a1947f7"
+		"sourceHash": "49ccb021fb60c45cdbe234241549e468ba556277d74d824145ca8707ff2bc908"
 	},
 	{
 		"file": "packages/editor/src/resolved-layer.tsx",
@@ -487,7 +487,7 @@
 				1
 			]
 		],
-		"sourceHash": "1267a15ad057c3d48bc475e033c5970731e97dcf8ac0baa212726b225c38e377"
+		"sourceHash": "74045d002ca932fa97d57774c0d4c4e36b19bb30daa92703a322595de22e37f5"
 	},
 	{
 		"file": "packages/editor/src/resolved-layer.tsx",
@@ -501,6 +501,6 @@
 				1
 			]
 		],
-		"sourceHash": "1267a15ad057c3d48bc475e033c5970731e97dcf8ac0baa212726b225c38e377"
+		"sourceHash": "74045d002ca932fa97d57774c0d4c4e36b19bb30daa92703a322595de22e37f5"
 	}
 ]
diff --git a/scripts/design-contract/exceptions/dynamic-packages.json b/scripts/design-contract/exceptions/dynamic-packages.json
index 8050eeb51..e85e4153a 100644
--- a/scripts/design-contract/exceptions/dynamic-packages.json
+++ b/scripts/design-contract/exceptions/dynamic-packages.json
@@ -746,6 +746,6 @@
 				1
 			]
 		],
-		"sourceHash": "b6454ae171e15bf7a00d5cfc6ca34141ea34f87484d16dead55c6ae9dfc3ea09"
+		"sourceHash": "5c9709fd97d4f6777205da118ce8b24123537b0ae7e56d3fa4490db8538081bf"
 	}
 ]