diff --git a/projects/plugins/jetpack/changelog/fix-remove-replace-button b/projects/plugins/jetpack/changelog/fix-remove-replace-button
new file mode 100644
index 0000000000000..0fe7e60101d99
--- /dev/null
+++ b/projects/plugins/jetpack/changelog/fix-remove-replace-button
@@ -0,0 +1,4 @@
+Significance: patch
+Type: bugfix
+
+Media Buttons: don't show duplicate buttons when a featured image is selected
\ No newline at end of file
diff --git a/projects/plugins/jetpack/extensions/shared/external-media/editor.scss b/projects/plugins/jetpack/extensions/shared/external-media/editor.scss
index 8d8a3d46f77f6..2e9e4859f32fc 100644
--- a/projects/plugins/jetpack/extensions/shared/external-media/editor.scss
+++ b/projects/plugins/jetpack/extensions/shared/external-media/editor.scss
@@ -413,5 +413,6 @@ $grid-size: 8px;
 .editor-post-featured-image {
 	.components-dropdown .jetpack-external-media-button-menu {
 		margin-right: 8px;
+		margin-bottom: 1em;
 	}
 }
diff --git a/projects/plugins/jetpack/extensions/shared/external-media/index.js b/projects/plugins/jetpack/extensions/shared/external-media/index.js
index 7a274185376f7..7d5fac3fdb10d 100644
--- a/projects/plugins/jetpack/extensions/shared/external-media/index.js
+++ b/projects/plugins/jetpack/extensions/shared/external-media/index.js
@@ -50,6 +50,12 @@ if ( isCurrentUserConnected() && 'function' === typeof useBlockEditContext ) {
 			const { name } = useBlockEditContext();
 			let { render } = props;
 
+			// Featured Image gets rendered twice in the Post sidebar when an image is selected.
+			// We only want the first of the two, which conveniently has a value prop
+			if ( isFeaturedImage( props ) && props.value === undefined ) {
+				return <></>;
+			}
+
 			if ( isAllowedBlock( name, render ) || isFeaturedImage( props ) ) {
 				const { allowedTypes, gallery = false, value = [] } = props;
 
diff --git a/projects/plugins/jetpack/extensions/shared/external-media/media-button/media-menu.js b/projects/plugins/jetpack/extensions/shared/external-media/media-button/media-menu.js
index 169f625f28e5d..fd956c98a0640 100644
--- a/projects/plugins/jetpack/extensions/shared/external-media/media-button/media-menu.js
+++ b/projects/plugins/jetpack/extensions/shared/external-media/media-button/media-menu.js
@@ -13,10 +13,10 @@ import MediaSources from './media-sources';
 function MediaButtonMenu( props ) {
 	const { mediaProps, open, setSelectedSource, isFeatured, isReplace } = props;
 	const originalComponent = mediaProps.render;
-
-	if ( isFeatured && mediaProps.value === undefined ) {
-		return originalComponent( { open } );
-	}
+	const featuredImageIsSelected = isFeatured && mediaProps.value > 0;
+	let isPrimary = isFeatured;
+	let isTertiary = ! isFeatured;
+	const extraProps = {};
 
 	if ( isReplace ) {
 		return (
@@ -38,6 +38,13 @@ function MediaButtonMenu( props ) {
 		label = __( 'Select Media', 'jetpack' );
 	}
 
+	if ( isFeatured && featuredImageIsSelected ) {
+		label = __( 'Replace Image', 'jetpack' );
+		isPrimary = false;
+		isTertiary = false;
+		extraProps.isSecondary = true;
+	}
+
 	return (
 		<>
 			{ isFeatured && originalComponent( { open } ) }
@@ -47,12 +54,13 @@ function MediaButtonMenu( props ) {
 				contentClassName="jetpack-external-media-button-menu__options"
 				renderToggle={ ( { isOpen, onToggle } ) => (
 					<Button
-						isTertiary={ ! isFeatured }
-						isPrimary={ isFeatured }
+						isTertiary={ isTertiary }
+						isPrimary={ isPrimary }
 						className="jetpack-external-media-button-menu"
 						aria-haspopup="true"
 						aria-expanded={ isOpen }
 						onClick={ onToggle }
+						{ ...extraProps }
 					>
 						{ label }
 					</Button>