diff --git a/projects/js-packages/licensing/changelog/update-license-activate-error-messages b/projects/js-packages/licensing/changelog/update-license-activate-error-messages
new file mode 100644
index 0000000000000..fb61373a9d180
--- /dev/null
+++ b/projects/js-packages/licensing/changelog/update-license-activate-error-messages
@@ -0,0 +1,4 @@
+Significance: minor
+Type: changed
+
+Add more helpful error messages and help steps on license key activation error.
diff --git a/projects/js-packages/licensing/components/activation-screen-controls/index.jsx b/projects/js-packages/licensing/components/activation-screen-controls/index.jsx
index 72231125acb58..51bbfa6af8d0a 100644
--- a/projects/js-packages/licensing/components/activation-screen-controls/index.jsx
+++ b/projects/js-packages/licensing/components/activation-screen-controls/index.jsx
@@ -3,10 +3,10 @@ import { JetpackLogo, Spinner } from '@automattic/jetpack-components';
 import { Button, TextControl, SelectControl } from '@wordpress/components';
 import { createInterpolateElement } from '@wordpress/element';
 import { sprintf, __ } from '@wordpress/i18n';
-import { Icon, warning } from '@wordpress/icons';
 import PropTypes from 'prop-types';
 import React, { useCallback, useEffect, useMemo, useState } from 'react';
-
+import ActivationScreenError from '../activation-screen-error';
+import { LICENSE_ERRORS } from '../activation-screen-error/constants';
 import './style.scss';
 
 /**
@@ -145,15 +145,26 @@ const ActivationScreenControls = props => {
 		licenseError,
 		onLicenseChange,
 	} = props;
-	const hasLicenseError = licenseError !== null && licenseError !== undefined;
 
 	useEffect( () => {
 		jetpackAnalytics.tracks.recordEvent( 'jetpack_wpa_license_key_activation_view' );
 	}, [] );
 
-	const className = hasLicenseError
-		? 'jp-license-activation-screen-controls--license-field-with-error'
-		: 'jp-license-activation-screen-controls--license-field';
+	const errorTypeMatch = licenseError?.match( /\[[a-z_]+\]/ );
+	const errorType = errorTypeMatch && errorTypeMatch[ 0 ];
+
+	const { ACTIVE_ON_SAME_SITE } = LICENSE_ERRORS;
+	const isLicenseAlreadyAttached = ACTIVE_ON_SAME_SITE === errorType;
+	const className = useMemo( () => {
+		if ( ! licenseError ) {
+			return 'jp-license-activation-screen-controls--license-field';
+		}
+		if ( isLicenseAlreadyAttached ) {
+			return 'jp-license-activation-screen-controls--license-field-with-success';
+		}
+
+		return 'jp-license-activation-screen-controls--license-field-with-error';
+	}, [ licenseError, isLicenseAlreadyAttached ] );
 
 	const hasAvailableLicenseKey = availableLicenses && availableLicenses.length;
 
@@ -189,11 +200,8 @@ const ActivationScreenControls = props => {
 						value={ license }
 					/>
 				) }
-				{ hasLicenseError && (
-					<div className="jp-license-activation-screen-controls--license-field-error">
-						<Icon icon={ warning } />
-						<span>{ licenseError }</span>
-					</div>
+				{ licenseError && (
+					<ActivationScreenError licenseError={ licenseError } errorType={ errorType } />
 				) }
 			</div>
 			<div>
diff --git a/projects/js-packages/licensing/components/activation-screen-controls/style.scss b/projects/js-packages/licensing/components/activation-screen-controls/style.scss
index b6b0a0a0c3c89..70c8974ea348e 100644
--- a/projects/js-packages/licensing/components/activation-screen-controls/style.scss
+++ b/projects/js-packages/licensing/components/activation-screen-controls/style.scss
@@ -37,7 +37,8 @@
 
 
 	.jp-license-activation-screen-controls--license-field,
-	.jp-license-activation-screen-controls--license-field-with-error {
+	.jp-license-activation-screen-controls--license-field-with-error,
+	.jp-license-activation-screen-controls--license-field-with-success {
 		max-width: 500px;
 		.components-input-control__label.components-input-control__label.components-input-control__label {
 			font-weight: 600;
@@ -67,21 +68,10 @@
 		}
 	}
 
-	.jp-license-activation-screen-controls--license-field-error {
-		display: flex;
-		flex-direction: row;
-		align-items: flex-start;
-		color: var(--jp-red);
-		max-width: 500px;
-
-		svg {
-			margin-right: 4px;
-			fill: var(--jp-red);
-			min-width: 24px;
-		}
-
-		span {
-			font-size: var(--font-body);
+	.jp-license-activation-screen-controls--license-field-with-success {
+		input.components-text-control__input,
+		select.components-select-control__input {
+			border: 1px solid var(--jp-green);
 		}
 	}
 
diff --git a/projects/js-packages/licensing/components/activation-screen-controls/test/component.jsx b/projects/js-packages/licensing/components/activation-screen-controls/test/component.jsx
index ad4fc05bdcbe8..b89a6d7c7e20d 100644
--- a/projects/js-packages/licensing/components/activation-screen-controls/test/component.jsx
+++ b/projects/js-packages/licensing/components/activation-screen-controls/test/component.jsx
@@ -47,7 +47,7 @@ describe( 'ActivationScreenControls', () => {
 			expect( node ).toBeInTheDocument();
 			expect(
 				// eslint-disable-next-line testing-library/no-node-access
-				node.closest( '.jp-license-activation-screen-controls--license-field-error' )
+				node.closest( '.activation-screen-error__message' )
 			).toBeInTheDocument();
 		} );
 	} );
diff --git a/projects/js-packages/licensing/components/activation-screen-error/constants.ts b/projects/js-packages/licensing/components/activation-screen-error/constants.ts
new file mode 100644
index 0000000000000..d971f2625d79a
--- /dev/null
+++ b/projects/js-packages/licensing/components/activation-screen-error/constants.ts
@@ -0,0 +1,9 @@
+export const LICENSE_ERRORS = {
+	NOT_SAME_OWNER: '[not_same_owner]',
+	ACTIVE_ON_SAME_SITE: '[active_on_same_site]',
+	ATTACHED_LICENSE: '[attached_license]',
+	PRODUCT_INCOMPATIBILITY: '[product_incompatibility]',
+	REVOKED_LICENSE: '[revoked_license]',
+	INVALID_INPUT: '[invalid_input]',
+	MULTISITE_INCOMPATIBILITY: '[multisite_incompatibility]',
+} as const;
diff --git a/projects/js-packages/licensing/components/activation-screen-error/index.tsx b/projects/js-packages/licensing/components/activation-screen-error/index.tsx
new file mode 100644
index 0000000000000..0eec02d2f214d
--- /dev/null
+++ b/projects/js-packages/licensing/components/activation-screen-error/index.tsx
@@ -0,0 +1,52 @@
+import jetpackAnalytics from '@automattic/jetpack-analytics';
+import { Icon, warning, check } from '@wordpress/icons';
+import React, { useEffect } from 'react';
+import { LICENSE_ERRORS } from './constants';
+import { useGetErrorContent } from './use-get-error-content';
+import type { FC } from 'react';
+
+import './style.scss';
+
+type LicenseErrorKeysType = keyof typeof LICENSE_ERRORS;
+type LicenseErrorValuesType = ( typeof LICENSE_ERRORS )[ LicenseErrorKeysType ];
+
+interface Props {
+	licenseError: string;
+	errorType: LicenseErrorValuesType;
+}
+
+const ActivationScreenError: FC< Props > = ( { licenseError, errorType } ) => {
+	useEffect( () => {
+		if ( licenseError ) {
+			jetpackAnalytics.tracks.recordEvent( 'jetpack_wpa_license_activation_error_view', {
+				error: licenseError,
+				error_type: errorType,
+			} );
+		}
+	}, [ licenseError, errorType ] );
+
+	const { errorMessage, errorInfo } = useGetErrorContent( licenseError, errorType );
+
+	if ( ! licenseError ) {
+		return null;
+	}
+
+	const { ACTIVE_ON_SAME_SITE } = LICENSE_ERRORS;
+	const isLicenseAlreadyAttached = ACTIVE_ON_SAME_SITE === errorType;
+
+	const errorMessageClass = isLicenseAlreadyAttached
+		? 'activation-screen-error__message--success'
+		: 'activation-screen-error__message--error';
+
+	return (
+		<>
+			<div className={ `activation-screen-error__message ${ errorMessageClass }` }>
+				<Icon icon={ isLicenseAlreadyAttached ? check : warning } size={ 20 } />
+				<span>{ errorMessage }</span>
+			</div>
+			{ errorInfo && <div className="activation-screen-error__info">{ errorInfo }</div> }
+		</>
+	);
+};
+
+export default ActivationScreenError;
diff --git a/projects/js-packages/licensing/components/activation-screen-error/style.scss b/projects/js-packages/licensing/components/activation-screen-error/style.scss
new file mode 100644
index 0000000000000..5e92e10f6ef6c
--- /dev/null
+++ b/projects/js-packages/licensing/components/activation-screen-error/style.scss
@@ -0,0 +1,75 @@
+.activation-screen-error__message {
+    display: flex;
+    flex-direction: row;
+    align-items: flex-start;
+    max-width: 500px;
+    margin-top: calc(var(--spacing-base)*.5);
+
+    svg {
+        margin-left: -3px;
+    }
+
+    span {
+        font-size: 13px;
+        line-height: 20px;
+        font-weight: 500;
+        letter-spacing: -0.044em;
+    }
+}
+
+.activation-screen-error__message--error {
+    color: var(--jp-red);
+    svg {
+        fill: var(--jp-red);
+    }
+}
+
+.activation-screen-error__message--success {
+    color: var(--jp-green);
+    svg {
+        fill: var(--jp-green);
+    }
+}
+
+.activation-screen-error__info {
+    background-color: var(--jp-gray-0);
+    color: var(--jp-gray-80);
+    font-size: var(--font-body-small);
+    line-height: calc(var(--font-title-small) - 2px);
+    border: 1px solid var(--jp-green-0);
+    border-radius: var(--jp-border-radius);
+    padding: var(--jp-modal-padding-small);
+    margin: 32px 0 8px;
+
+    > p {
+        margin: 0 0 1em;
+        font-size: var(--font-body-small);
+    }
+    > p:last-child {
+        margin-bottom: 0;
+    }
+
+    ol > li::marker {
+        font-weight: bold;
+    }
+
+    a {
+        color: var(--jp-green-50);
+    }
+    a:hover,
+    a:active {
+        color: var(--jp-green-70);
+    }
+}
+
+.jp-license-activation-screen-controls {
+    .activation-screen-error__info {
+        > p {
+            margin: 0 0 1em;
+            font-size: var(--font-body-small);
+        }
+        > p:last-child {
+            margin-bottom: 0;
+        }
+    }
+}
diff --git a/projects/js-packages/licensing/components/activation-screen-error/use-get-error-content.tsx b/projects/js-packages/licensing/components/activation-screen-error/use-get-error-content.tsx
new file mode 100644
index 0000000000000..45e259667611b
--- /dev/null
+++ b/projects/js-packages/licensing/components/activation-screen-error/use-get-error-content.tsx
@@ -0,0 +1,185 @@
+import { getRedirectUrl } from '@automattic/jetpack-components';
+import { ExternalLink } from '@wordpress/components';
+import { createInterpolateElement } from '@wordpress/element';
+import { __, sprintf } from '@wordpress/i18n';
+import React from 'react';
+import { LICENSE_ERRORS } from './constants';
+
+type LicenseErrorKeysType = keyof typeof LICENSE_ERRORS;
+type LicenseErrorValuesType = ( typeof LICENSE_ERRORS )[ LicenseErrorKeysType ];
+
+export const useGetErrorContent = ( licenseError: string, errorType: LicenseErrorValuesType ) => {
+	if ( ! licenseError ) {
+		return {
+			errorMessage: null,
+			errorInfo: null,
+		};
+	}
+
+	const needHelpGetInTouchLink = createInterpolateElement(
+		__( 'Need help? <a>Get in touch</a>.', 'jetpack' ),
+		{
+			a: (
+				<ExternalLink
+					href={ getRedirectUrl( 'jetpack-support-license-activation' ) }
+					rel="noopener noreferrer"
+				></ExternalLink>
+			),
+		}
+	);
+
+	switch ( errorType ) {
+		case LICENSE_ERRORS.NOT_SAME_OWNER:
+			return {
+				errorMessage: __(
+					'The account that purchased the plan and the account managing this site are different.',
+					'jetpack'
+				),
+				errorInfo: (
+					<>
+						<p>
+							{ createInterpolateElement(
+								__( 'Follow these <a>steps</a> to resolve it.', 'jetpack' ),
+								{
+									a: (
+										<ExternalLink
+											rel="noopener noreferrer"
+											href={ getRedirectUrl( 'jetpack-support-activate-license', {
+												anchor: 'different-user',
+											} ) }
+										></ExternalLink>
+									),
+								}
+							) }
+						</p>
+						<ol>
+							<li>{ __( 'Disconnect Jetpack from your site.', 'jetpack' ) }</li>
+							<li>
+								{ __( 'Log in to the WordPress.com account that purchased the plan.', 'jetpack' ) }
+							</li>
+							<li>{ __( 'Reconnect Jetpack.', 'jetpack' ) }</li>
+						</ol>
+						<p>{ needHelpGetInTouchLink }</p>
+					</>
+				),
+			};
+		case LICENSE_ERRORS.ACTIVE_ON_SAME_SITE:
+			return {
+				errorMessage: __( 'This license is already active on your site.', 'jetpack' ),
+				errorInfo: null,
+			};
+		case LICENSE_ERRORS.ATTACHED_LICENSE:
+			return {
+				errorMessage: __( 'This license is already active on another website', 'jetpack' ),
+				errorInfo: (
+					<ul>
+						<li>
+							{ createInterpolateElement(
+								__( 'If you would like to transfer it, please <a>get in touch</a>.', 'jetpack' ),
+								{
+									a: (
+										<ExternalLink
+											rel="noopener noreferrer"
+											href={ getRedirectUrl( 'jetpack-support-license-activation' ) }
+										></ExternalLink>
+									),
+								}
+							) }
+						</li>
+						<li>
+							{ createInterpolateElement(
+								__( 'To use Jetpack on both sites, please <a>buy another license</a>.', 'jetpack' ),
+								{
+									a: (
+										<ExternalLink
+											rel="noopener noreferrer"
+											href={ getRedirectUrl( 'my-jetpack-my-plans-purchase-no-site' ) }
+										></ExternalLink>
+									),
+								}
+							) }
+						</li>
+					</ul>
+				),
+			};
+		case LICENSE_ERRORS.PRODUCT_INCOMPATIBILITY:
+			return {
+				errorMessage: __(
+					'Your site already has an active Jetpack plan of equal or higher value.',
+					'jetpack'
+				),
+				errorInfo: (
+					<>
+						<p>
+							{ __(
+								'It looks like your website already has a Jetpack plan that’s equal to or better than the one you’re trying to activate.',
+								'jetpack'
+							) }
+						</p>
+
+						<p>
+							{ __(
+								'You can either use this license on a different site or cancel your current plan for a refund.',
+								'jetpack'
+							) }
+						</p>
+						<p>{ needHelpGetInTouchLink }</p>
+					</>
+				),
+			};
+		case LICENSE_ERRORS.REVOKED_LICENSE:
+			return {
+				errorMessage: __(
+					'The subscription is no longer active or has expired. Please purchase a new license.',
+					'jetpack'
+				),
+				errorInfo: <p>{ needHelpGetInTouchLink }</p>,
+			};
+		case LICENSE_ERRORS.INVALID_INPUT:
+			return {
+				errorMessage: __( 'Unable to validate this license key.', 'jetpack' ),
+				errorInfo: (
+					<>
+						<p>
+							{ __(
+								'Please take a moment to check the license key from your purchase confirmation email—it might have a small typo.',
+								'jetpack'
+							) }
+						</p>
+
+						<p>{ needHelpGetInTouchLink }</p>
+					</>
+				),
+			};
+		case LICENSE_ERRORS.MULTISITE_INCOMPATIBILITY: {
+			const planNameMatch = licenseError.match( /We.re sorry, (.*) is not compatible/ );
+			const planName = planNameMatch && planNameMatch[ 1 ];
+			return {
+				errorMessage: sprintf(
+					/* translators: %s is the Jetpack product name, i.e.- Jetpack Backup, Jetpack Boost, etc., which the product name should not be translated. */
+					__(
+						'We’re sorry, %s is not compatible with multisite WordPress installations at this time.',
+						'jetpack'
+					),
+					planName
+				),
+				errorInfo: (
+					<>
+						<p>
+							{ __(
+								'This Jetpack plan doesn’t work with Multisite WordPress setups. Please use it on a single-site installation or consider canceling for a refund.',
+								'jetpack'
+							) }
+						</p>
+						<p>{ needHelpGetInTouchLink }</p>
+					</>
+				),
+			};
+		}
+		default:
+			return {
+				errorMessage: licenseError,
+				errorInfo: <p>{ needHelpGetInTouchLink }</p>,
+			};
+	}
+};