diff --git a/.changeset/legal-lands-warn.md b/.changeset/legal-lands-warn.md
new file mode 100644
index 00000000000..63e5aac327d
--- /dev/null
+++ b/.changeset/legal-lands-warn.md
@@ -0,0 +1,54 @@
+---
+"@spectrum-css/contextualhelp": major
+---
+
+#### S2 migration for contextual help
+
+This migrates the contextual help component to the latest Spectrum 2 designs. Custom properties have been remapped and added per the design specification.
+
+Typographic and color tokens have been updated per design specifications.
+
+All existing popover positioning variations are supported.
+
+##### New custom properties
+
+`--spectrum-contextual-help-body-color`
+`--spectrum-contextual-help-body-line-height`
+`--spectrum-contextual-help-body-sans-serif-font-family`
+`--spectrum-contextual-help-body-sans-serif-font-style`
+`--spectrum-contextual-help-body-sans-serif-font-weight`
+`--spectrum-contextual-help-title-color`
+`--spectrum-contextual-help-title-font-style`
+`--spectrum-contextual-help-title-font-weight`
+`--spectrum-contextual-help-title-line-height`
+`--spectrum-contextual-help-title-sans-serif-font-family`
+
+##### New mods
+
+`--mod-contextual-help-body-line-height`
+`--mod-contextual-help-body-sans-serif-font-family`
+`--mod-contextual-help-body-sans-serif-font-style`
+`--mod-contextual-help-body-sans-serif-font-weight`
+`--mod-contextual-help-body-size`
+`--mod-contextual-help-title-color`
+`--mod-contextual-help-title-font-style`
+`--mod-contextual-help-title-font-weight`
+`--mod-contextual-help-title-line-height`
+`--mod-contextual-help-title-sans-serif-font-family`
+`--mod-contextual-help-content-spacing`
+`--mod-contextual-help-heading-size`
+`--mod-contextual-help-link-spacing`
+`--mod-contextual-help-min-inline-size`
+`--mod-contextual-help-padding`
+`--mod-contextual-help-popover-maximum-width`
+
+##### Removed mods
+
+`--mod-contextual-help-title-sans-serif-font-family`
+`--mod-spectrum-contextual-help-body-size`
+`--mod-spectrum-contextual-help-content-spacing`
+`--mod-spectrum-contextual-help-heading-size`
+`--mod-spectrum-contextual-help-link-spacing`
+`--mod-spectrum-contextual-help-minimum-width`
+`--mod-spectrum-contextual-help-padding`
+`--mod-spectrum-contextual-help-popover-maximum-width`
diff --git a/components/contextualhelp/dist/metadata.json b/components/contextualhelp/dist/metadata.json
index 8711f77b47f..a64ded05750 100644
--- a/components/contextualhelp/dist/metadata.json
+++ b/components/contextualhelp/dist/metadata.json
@@ -10,30 +10,63 @@
   ],
   "modifiers": [
     "--mod-contextual-help-body-color",
-    "--mod-contextual-help-heading-color",
-    "--mod-spectrum-contextual-help-body-size",
-    "--mod-spectrum-contextual-help-content-spacing",
-    "--mod-spectrum-contextual-help-heading-size",
-    "--mod-spectrum-contextual-help-link-spacing",
-    "--mod-spectrum-contextual-help-minimum-width",
-    "--mod-spectrum-contextual-help-padding",
-    "--mod-spectrum-contextual-help-popover-maximum-width"
+    "--mod-contextual-help-body-line-height",
+    "--mod-contextual-help-body-sans-serif-font-family",
+    "--mod-contextual-help-body-sans-serif-font-style",
+    "--mod-contextual-help-body-sans-serif-font-weight",
+    "--mod-contextual-help-body-size",
+    "--mod-contextual-help-content-spacing",
+    "--mod-contextual-help-heading-size",
+    "--mod-contextual-help-link-spacing",
+    "--mod-contextual-help-min-inline-size",
+    "--mod-contextual-help-padding",
+    "--mod-contextual-help-popover-maximum-width",
+    "--mod-contextual-help-title-color",
+    "--mod-contextual-help-title-font-style",
+    "--mod-contextual-help-title-font-weight",
+    "--mod-contextual-help-title-line-height",
+    "--mod-contextual-help-title-sans-serif-font-family"
   ],
   "component": [
+    "--spectrum-contextual-help-body-color",
+    "--spectrum-contextual-help-body-line-height",
+    "--spectrum-contextual-help-body-sans-serif-font-family",
+    "--spectrum-contextual-help-body-sans-serif-font-style",
+    "--spectrum-contextual-help-body-sans-serif-font-weight",
     "--spectrum-contextual-help-body-size",
     "--spectrum-contextual-help-content-spacing",
+    "--spectrum-contextual-help-link-spacing",
+    "--spectrum-contextual-help-min-inline-size",
     "--spectrum-contextual-help-minimum-width",
+    "--spectrum-contextual-help-padding",
+    "--spectrum-contextual-help-title-color",
+    "--spectrum-contextual-help-title-font-style",
+    "--spectrum-contextual-help-title-font-weight",
+    "--spectrum-contextual-help-title-line-height",
+    "--spectrum-contextual-help-title-sans-serif-font-family",
     "--spectrum-contextual-help-title-size"
   ],
   "global": [
     "--spectrum-body-color",
-    "--spectrum-heading-color",
+    "--spectrum-body-sans-serif-font-style",
+    "--spectrum-body-sans-serif-font-weight",
+    "--spectrum-corner-radius-large-default",
+    "--spectrum-line-height-200",
+    "--spectrum-sans-font-family-stack",
+    "--spectrum-spacing-100",
     "--spectrum-spacing-300",
-    "--spectrum-spacing-400"
+    "--spectrum-spacing-400",
+    "--spectrum-title-color",
+    "--spectrum-title-line-height",
+    "--spectrum-title-sans-serif-font-style",
+    "--spectrum-title-sans-serif-font-weight"
+  ],
+  "passthroughs": [
+    "--mod-popover-animation-distance",
+    "--mod-popover-corner-radius"
   ],
-  "passthroughs": [],
   "high-contrast": [
     "--highcontrast-contextual-help-body-color",
-    "--highcontrast-contextual-help-heading-color"
+    "--highcontrast-contextual-help-title-color"
   ]
 }
diff --git a/components/contextualhelp/index.css b/components/contextualhelp/index.css
index 68152fd353b..c416b8395c0 100644
--- a/components/contextualhelp/index.css
+++ b/components/contextualhelp/index.css
@@ -1,5 +1,5 @@
 /*!
- * Copyright 2024 Adobe. All rights reserved.
+ * Copyright 2025 Adobe. All rights reserved.
  *
  * This file is licensed to you under the Apache License, Version 2.0 (the "License");
  * you may not use this file except in compliance with the License. You may obtain a copy
@@ -11,9 +11,34 @@
  * governing permissions and limitations under the License.
  */
 
+.spectrum-ContextualHelp {
+	--spectrum-contextual-help-title-sans-serif-font-family: var(--spectrum-sans-font-family-stack);
+	--spectrum-contextual-help-title-font-weight: var(--spectrum-title-sans-serif-font-weight);
+	--spectrum-contextual-help-title-font-style: var(--spectrum-title-sans-serif-font-style);
+	--spectrum-contextual-help-title-line-height: var(--spectrum-title-line-height);
+
+	--spectrum-contextual-help-title-color: var(--spectrum-title-color);
+
+	--spectrum-contextual-help-body-sans-serif-font-family: var(--spectrum-sans-font-family-stack);
+	--spectrum-contextual-help-body-sans-serif-font-weight: var(--spectrum-body-sans-serif-font-weight);
+	--spectrum-contextual-help-body-sans-serif-font-style: var(--spectrum-body-sans-serif-font-style);
+	--spectrum-contextual-help-body-line-height: var(--spectrum-line-height-200);
+
+	--spectrum-contextual-help-body-color: var(--spectrum-body-color);
+
+	--spectrum-contextual-help-min-inline-size: var(--spectrum-contextual-help-minimum-width);
+	--spectrum-contextual-help-link-spacing: var(--spectrum-spacing-300);
+	--spectrum-contextual-help-padding: var(--spectrum-spacing-400);
+
+	/* @passthrough start */
+	--mod-popover-animation-distance: var(--spectrum-spacing-100);
+	--mod-popover-corner-radius: var(--spectrum-corner-radius-large-default);
+	/* @passthrough end */
+}
+
 .spectrum-ContextualHelp {
 	position: relative;
-	min-inline-size: var(--mod-spectrum-contextual-help-minimum-width, var(--spectrum-contextual-help-minimum-width));
+	min-inline-size: var(--mod-contextual-help-min-inline-size, var(--spectrum-contextual-help-min-inline-size));
 }
 
 .spectrum-ContextualHelp-button {
@@ -21,12 +46,11 @@
 }
 
 .spectrum-ContextualHelp-popover {
-	padding-block: var(--mod-spectrum-contextual-help-padding, var(--spectrum-spacing-400));
-	padding-inline: var(--mod-spectrum-contextual-help-padding, var(--spectrum-spacing-400));
-	font-size: var(--mod-spectrum-contextual-help-body-size, var(--spectrum-contextual-help-body-size));
+	padding: var(--mod-contextual-help-padding, var(--spectrum-contextual-help-padding));
+	font-size: var(--mod-contextual-help-body-size, var(--spectrum-contextual-help-body-size));
 	color: var(--highcontrast-contextual-help-body-color, var(--mod-contextual-help-body-color, var(--spectrum-body-color)));
 
-	max-inline-size: var(--mod-spectrum-contextual-help-popover-maximum-width);
+	max-inline-size: var(--mod-contextual-help-popover-maximum-width);
 
 	.spectrum-ContextualHelp-heading,
 	.spectrum-ContextualHelp-body {
@@ -34,19 +58,32 @@
 	}
 
 	.spectrum-ContextualHelp-heading {
-		margin-block-end: var(--mod-spectrum-contextual-help-content-spacing, var(--spectrum-contextual-help-content-spacing));
-		font-size: var(--mod-spectrum-contextual-help-heading-size, var(--spectrum-contextual-help-title-size));
-		color: var(--highcontrast-contextual-help-heading-color, var(--mod-contextual-help-heading-color, var(--spectrum-heading-color)));
+		font-family: var(--mod-contextual-help-title-sans-serif-font-family, var(--spectrum-contextual-help-title-sans-serif-font-family));
+		font-weight: var(--mod-contextual-help-title-font-weight, var(--spectrum-contextual-help-title-font-weight));
+		font-size: var(--mod-contextual-help-heading-size, var(--spectrum-contextual-help-title-size));
+		font-style: var(--mod-contextual-help-title-font-style, var(--spectrum-contextual-help-title-font-style));
+		line-height: var(--mod-contextual-help-title-line-height, var(--spectrum-contextual-help-title-line-height));
+		color: var(--highcontrast-contextual-help-title-color, var(--mod-contextual-help-title-color, var(--spectrum-contextual-help-title-color)));
+		margin-block-end: var(--mod-contextual-help-content-spacing, var(--spectrum-contextual-help-content-spacing));
+	}
+
+	.spectrum-ContextualHelp-body {
+		font-size: var(--mod-contextual-help-body-size, var(--spectrum-contextual-help-body-size));
+		font-family: var(--mod-contextual-help-body-sans-serif-font-family, var(--spectrum-contextual-help-body-sans-serif-font-family));
+		font-weight: var(--mod-contextual-help-body-sans-serif-font-weight, var(--spectrum-contextual-help-body-sans-serif-font-weight));
+		font-style: var(--mod-contextual-help-body-sans-serif-font-style, var(--spectrum-contextual-help-body-sans-serif-font-style));
+		line-height: var(--mod-contextual-help-body-line-height, var(--spectrum-contextual-help-body-line-height));
+		color: var(--mod-contextual-help-body-color, var(--spectrum-contextual-help-body-color));
 	}
 }
 
 .spectrum-ContextualHelp-link {
-	margin-block-start: var(--mod-spectrum-contextual-help-link-spacing, var(--spectrum-spacing-300));
+	margin-block-start: var(--mod-contextual-help-link-spacing, var(--spectrum-contextual-help-link-spacing));
 }
 
 @media (forced-colors: active) {
 	.spectrum-ContextualHelp {
-		--highcontrast-contextual-help-heading-color: CanvasText;
+		--highcontrast-contextual-help-title-color: CanvasText;
 		--highcontrast-contextual-help-body-color: CanvasText;
 	}
 }
diff --git a/components/contextualhelp/stories/contextualhelp.stories.js b/components/contextualhelp/stories/contextualhelp.stories.js
index 4b7abd0296a..117912f633b 100644
--- a/components/contextualhelp/stories/contextualhelp.stories.js
+++ b/components/contextualhelp/stories/contextualhelp.stories.js
@@ -31,13 +31,13 @@ export default {
 		iconName: {
 			name: "Icon",
 			type: { name: "string", required: true },
-			defaultValue: "Info",
+			defaultValue: "InfoCircle",
 			table: {
 				type: { summary: "string" },
 				category: "Component",
 				defaultValue: { summary: "Info" },
 			},
-			options: ["Info", "Help"],
+			options: ["InfoCircle", "HelpCircle"],
 			control: "select",
 		},
 		iconSet: { table: { disable: true } },
@@ -76,16 +76,26 @@ export default {
 			],
 			control: "select",
 		},
-		link: { table: { disable: true } },
+		link: {
+			name: "Has link",
+			type: { name: "boolean", required: false },
+			defaultValue: false,
+			table: {
+				summary: "boolean",
+				category: "Component",
+				defaultValue: { summary: false }
+			}
+		},
 	},
 	args: {
 		rootClass: "spectrum-ContextualHelp",
-		iconName: "Info",
+		iconName: "InfoCircle",
 		iconSet: "workflow",
 		popoverPlacement: "bottom-start",
+		link: false,
 		title: "Permission required",
 		body: "Your admin must grant you permission before you can create a new document. Please contact your admin for more information.",
-		customStyles: { "inline-size": "275px" },
+		customStyles: { "inline-size": "var(--spectrum-contextual-help-min-inline-size)" },
 	},
 	parameters: {
 		actions: {
@@ -102,7 +112,11 @@ export default {
 				height: "200px",
 			},
 		},
+		status: {
+			type: "migrated",
+		},
 	},
+	tags: ["migrated"]
 };
 
 /**
@@ -130,28 +144,6 @@ WithLink.parameters = {
 };
 WithLink.storyName = "Default - info icon with link";
 
-/**
- * In order to further customize the contextual help popover, implementations can set `--mod-spectrum-contextual-help-popover-maximum-width` to their desired max width.
- */
-export const MaxWidthPopover = Template.bind({});
-MaxWidthPopover.tags = ["!dev"];
-MaxWidthPopover.args = {
-	customStyles: {
-		"inline-size": "275px",
-		"--mod-spectrum-contextual-help-popover-maximum-width": "180px",
-		"margin-bottom": "270px",
-	},
-};
-MaxWidthPopover.parameters = {
-	chromatic: { disableSnapshot: true },
-	docs: {
-		story: {
-			height: "auto",
-		},
-	},
-};
-MaxWidthPopover.storyName = "Default - max width popover";
-
 /**
  * This is an example of the contextual help component within a popover with a placement of `top`. Read more about the 22 available placement positions in the [popover documentation](/docs/components-popover--docs).
  */
@@ -160,7 +152,6 @@ TopPopover.tags = ["!dev"];
 TopPopover.args = {
 	popoverPlacement: "top",
 	customStyles: {
-		"inline-size": "275px",
 		"margin-top": "170px",
 	},
 };
@@ -176,11 +167,13 @@ TopPopover.storyName = "Default - top popover";
 
 /**
  * When displaying help or resources to learn more, the contextual help should use the help icon. The content in this variant provides more detailed, in-depth guidance about a task, UI element, tool or keyboard shortcuts.
+ *
+ * All variants and positions of the contextual help component can be configured with a help icon.
  */
 export const HelpDefault = Template.bind({});
 HelpDefault.tags = ["!dev"];
 HelpDefault.args = {
-	iconName: "Help",
+	iconName: "HelpCircle",
 	title: "Need help?",
 };
 HelpDefault.parameters = {
@@ -188,66 +181,6 @@ HelpDefault.parameters = {
 };
 HelpDefault.storyName = "Help icon";
 
-export const HelpWithLink = Template.bind({});
-HelpWithLink.tags = ["!dev"];
-HelpWithLink.args = {
-	link: {
-		text: "Learn about permissions",
-		url: "#",
-	},
-	iconName: "Help",
-	title: "Need help?",
-	body: "Reach out to your admin for help regarding the document you are trying to create.",
-};
-HelpWithLink.parameters = {
-	chromatic: { disableSnapshot: true },
-};
-HelpWithLink.storyName = "Help icon - with link";
-
-export const HelpTopPopover = Template.bind({});
-HelpTopPopover.tags = ["!dev"];
-HelpTopPopover.args = {
-	popoverPlacement: "top",
-	customStyles: {
-		"inline-size": "275px",
-		"margin-top": "170px",
-	},
-	title: "Need help?",
-	body: "Reach out to your admin for help regarding the document you are trying to create.",
-	iconName: "Help",
-};
-HelpTopPopover.parameters = {
-	chromatic: { disableSnapshot: true },
-	docs: {
-		story: {
-			height: "auto",
-		},
-	},
-};
-HelpTopPopover.storyName = "Help icon - top popover";
-
-export const HelpMaxWidthPopover = Template.bind({});
-HelpMaxWidthPopover.tags = ["!dev"];
-HelpMaxWidthPopover.args = {
-	customStyles: {
-		"inline-size": "275px",
-		"--mod-spectrum-contextual-help-popover-maximum-width": "180px",
-		"margin-bottom": "270px",
-	},
-	title: "Need help?",
-	body: "Reach out to your admin for help regarding the document you are trying to create.",
-	iconName: "Help",
-};
-HelpMaxWidthPopover.parameters = {
-	chromatic: { disableSnapshot: true },
-	docs: {
-		story: {
-			height: "auto",
-		},
-	},
-};
-HelpMaxWidthPopover.storyName = "Help icon - max width popover";
-
 // ********* VRT ONLY ********* //
 export const WithForcedColors = ContextualHelpGroup.bind({});
 WithForcedColors.args = Default.args;
diff --git a/components/contextualhelp/stories/contextualhelp.test.js b/components/contextualhelp/stories/contextualhelp.test.js
index 7fea0b99dc3..c0b64328f14 100644
--- a/components/contextualhelp/stories/contextualhelp.test.js
+++ b/components/contextualhelp/stories/contextualhelp.test.js
@@ -8,15 +8,7 @@ export const ContextualHelpGroup = Variants({
 			testHeading: "Default",
 			customStyles: {
 				"inline-size": "275px",
-				"margin-bottom": "170px",
-			},
-		},
-		{
-			testHeading: "Max-width popover",
-			customStyles: {
-				"inline-size": "275px",
-				"margin-bottom": "275px",
-				"--mod-spectrum-contextual-help-popover-maximum-width": "150px",
+				"margin-bottom": "200px",
 			},
 		},
 		{
@@ -25,17 +17,14 @@ export const ContextualHelpGroup = Variants({
 				"inline-size": "275px",
 				"margin-bottom": "200px",
 			},
-			link: {
-				text: "Learn about permissions",
-				url: "#",
-			},
+			link: true,
 		},
 		{
 			testHeading: "Help",
-			iconName: "Help",
+			iconName: "HelpCircle",
 			customStyles: {
 				"inline-size": "275px",
-				"margin-bottom": "170px",
+				"margin-bottom": "200px",
 			},
 		},
 	],
diff --git a/components/contextualhelp/stories/template.js b/components/contextualhelp/stories/template.js
index aaeac140d32..f6097cfd151 100644
--- a/components/contextualhelp/stories/template.js
+++ b/components/contextualhelp/stories/template.js
@@ -21,6 +21,9 @@ export const Template = ({
 	customStyles = {},
 	customClasses = [],
 } = {}, context = {}) => {
+	const { globals = {} } = context;
+	const scale = globals.scale ?? "medium";
+
 	return html`
 		<div
 			class=${classMap({
@@ -34,7 +37,7 @@ export const Template = ({
 				isOpen: true,
 				trigger: (passthrough) => ActionButton({
 					...passthrough,
-					size: "xs",
+					size: scale === "medium" ? "xs" : "s",
 					iconName,
 					iconSet,
 					customClasses: [`${rootClass}-button`],
@@ -44,8 +47,8 @@ export const Template = ({
 					body ? html`<p class="${rootClass}-body">${body}</p>` : "",
 					link
 						? Link({
-								text: link.text,
-								url: link.url,
+								text: "Link text",
+								url: "#",
 								customClasses: [`${rootClass}-link`],
 						})
 						: nothing,