diff --git a/projects/plugins/jetpack/changelog/change-jetpack-ai-featured-image-show-current b/projects/plugins/jetpack/changelog/change-jetpack-ai-featured-image-show-current
new file mode 100644
index 0000000000000..84db90c3cf89e
--- /dev/null
+++ b/projects/plugins/jetpack/changelog/change-jetpack-ai-featured-image-show-current
@@ -0,0 +1,4 @@
+Significance: minor
+Type: other
+
+Jetpack AI: featured image generator modal noww shows current featured image if present
diff --git a/projects/plugins/jetpack/extensions/plugins/ai-assistant-plugin/components/ai-image/components/carrousel.scss b/projects/plugins/jetpack/extensions/plugins/ai-assistant-plugin/components/ai-image/components/carrousel.scss
index fe4e880a78200..e6532f4ed5085 100644
--- a/projects/plugins/jetpack/extensions/plugins/ai-assistant-plugin/components/ai-image/components/carrousel.scss
+++ b/projects/plugins/jetpack/extensions/plugins/ai-assistant-plugin/components/ai-image/components/carrousel.scss
@@ -1,3 +1,5 @@
+$scale-factor: 0.55;
+
 .ai-assistant-image {
 	&__blank {
 		display: flex;
@@ -47,6 +49,7 @@
 			display: flex;
 			align-items: center;
 			overflow: hidden;
+			height: calc( 768px * $scale-factor );
 
 			.ai-carrousel {
 				&__prev {
@@ -97,7 +100,7 @@
 
 		&-footer-left {
 			display: flex;
-			width: 25%;
+			flex-grow: 1;
 		}
 
 		&-counter {
@@ -106,7 +109,6 @@
 			align-items: center;
 			font-size: 13px;
 			padding: 6px 0;
-			width: 50%;
 
 			.ai-carrousel {
 				&__prev,
@@ -129,14 +131,17 @@
 		}
 
 		&-image {
-			width: 78%;
+			max-height: calc( 768px * $scale-factor );
+			max-width: calc( 1024px * $scale-factor );
+			width: auto;
 			height: auto;
+			margin: auto 0;
 		}
 
 		&-image-container {
 			display: flex;
 			width: 100%;
-			height: auto;
+			height: 100%;
 			position: absolute;
 			left: 8px;
 			transform: translateX( 100% );
diff --git a/projects/plugins/jetpack/extensions/plugins/ai-assistant-plugin/components/ai-image/components/carrousel.tsx b/projects/plugins/jetpack/extensions/plugins/ai-assistant-plugin/components/ai-image/components/carrousel.tsx
index f9dec07e3cb2b..d352fc985ecab 100644
--- a/projects/plugins/jetpack/extensions/plugins/ai-assistant-plugin/components/ai-image/components/carrousel.tsx
+++ b/projects/plugins/jetpack/extensions/plugins/ai-assistant-plugin/components/ai-image/components/carrousel.tsx
@@ -3,6 +3,7 @@
  */
 import { AiFeedbackThumbs } from '@automattic/jetpack-ai-client';
 import { Spinner } from '@wordpress/components';
+import { useEffect, useState } from '@wordpress/element';
 import { __ } from '@wordpress/i18n';
 import { Icon, chevronLeft, chevronRight } from '@wordpress/icons';
 import clsx from 'clsx';
@@ -62,6 +63,7 @@ export default function Carrousel( {
 	handleNextImage: () => void;
 	actions?: React.JSX.Element;
 } ) {
+	const [ imageFeedbackDisabled, setImageFeedbackDisabled ] = useState( false );
 	const prevButton = (
 		<button className="ai-carrousel__prev" onClick={ handlePreviousImage }>
 			<Icon
@@ -84,33 +86,37 @@ export default function Carrousel( {
 		</button>
 	);
 
-	const total = images?.filter?.( item => item?.generating || Object.hasOwn( item, 'image' ) )
-		?.length;
+	const total = images?.filter?.(
+		item => item?.generating || Object.hasOwn( item, 'image' ) || Object.hasOwn( item, 'libraryId' )
+	)?.length;
 
 	const actual = current === 0 && total === 0 ? 0 : current + 1;
 
-	const aiFeedbackDisabled = imageData => {
-		const { image, generating, error } = imageData;
+	useEffect( () => {
+		const imageData = images[ current ];
+		if ( ! imageData ) {
+			setImageFeedbackDisabled( true );
+		}
+
+		const { image, generating, error } = imageData || {};
 
 		// disable if there's an empty modal
 		if ( ! image && ! generating && ! error ) {
-			return true;
+			return setImageFeedbackDisabled( true );
 		}
-
 		// also disable if we're generating or have an error
 		if ( generating || error ) {
-			return true;
+			return setImageFeedbackDisabled( true );
 		}
 
-		// otherwise we're fine
-		return false;
-	};
+		setImageFeedbackDisabled( false );
+	}, [ current, images ] );
 
 	return (
 		<div className="ai-assistant-image__carrousel">
 			<div className="ai-assistant-image__carrousel-images">
 				{ images.length > 1 && prevButton }
-				{ images.map( ( { image, generating, error, revisedPrompt }, index ) => (
+				{ images.map( ( { image, generating, error, revisedPrompt, libraryUrl }, index ) => (
 					<div
 						key={ `image:` + index }
 						className={ clsx( 'ai-assistant-image__carrousel-image-container', {
@@ -146,14 +152,14 @@ export default function Carrousel( {
 									</BlankImage>
 								) : (
 									<>
-										{ ! generating && ! image ? (
+										{ ! generating && ! image && ! libraryUrl ? (
 											<BlankImage>
 												<AiIcon />
 											</BlankImage>
 										) : (
 											<img
 												className="ai-assistant-image__carrousel-image"
-												src={ image }
+												src={ image || libraryUrl }
 												alt={ revisedPrompt }
 											/>
 										) }
@@ -174,8 +180,8 @@ export default function Carrousel( {
 					</div>
 
 					<AiFeedbackThumbs
-						disabled={ aiFeedbackDisabled( images[ current ] ) }
-						ratedItem={ images[ current ].libraryUrl || '' }
+						disabled={ imageFeedbackDisabled }
+						ratedItem={ images[ current ]?.libraryUrl || '' }
 						iconSize={ 20 }
 						options={ {
 							mediaLibraryId: Number( images[ current ].libraryId ),
diff --git a/projects/plugins/jetpack/extensions/plugins/ai-assistant-plugin/components/ai-image/featured-image.tsx b/projects/plugins/jetpack/extensions/plugins/ai-assistant-plugin/components/ai-image/featured-image.tsx
index c132f83211bc2..36d414b05ac1b 100644
--- a/projects/plugins/jetpack/extensions/plugins/ai-assistant-plugin/components/ai-image/featured-image.tsx
+++ b/projects/plugins/jetpack/extensions/plugins/ai-assistant-plugin/components/ai-image/featured-image.tsx
@@ -5,6 +5,7 @@ import { ImageStyle } from '@automattic/jetpack-ai-client';
 import { useAnalytics } from '@automattic/jetpack-shared-extension-utils';
 import { Button } from '@wordpress/components';
 import { useDispatch, useSelect } from '@wordpress/data';
+import { store as editorStore } from '@wordpress/editor';
 import { useCallback, useState } from '@wordpress/element';
 import { __, sprintf } from '@wordpress/i18n';
 import debugFactory from 'debug';
@@ -30,6 +31,7 @@ import {
 	PLACEMENT_MEDIA_SOURCE_DROPDOWN,
 } from './types';
 import type { ImageResponse } from './hooks/use-ai-image';
+import type { EditorSelectors } from './types';
 
 const debug = debugFactory( 'jetpack-ai:featured-image' );
 
@@ -49,14 +51,16 @@ export default function FeaturedImage( {
 	);
 	const siteType = useSiteType();
 	const postContent = usePostContent();
-	const { postTitle, postFeaturedMedia } = useSelect( select => {
+	const { postTitle, postFeaturedMediaId, isEditorPanelOpened } = useSelect( select => {
 		return {
-			// @ts-expect-error - getEditedPostAttribute is not defined in the useSelect type
-			postTitle: select( 'core/editor' ).getEditedPostAttribute( 'title' ),
-			// @ts-expect-error - getEditedPostAttribute is not defined in the useSelect type
-			postFeaturedMedia: select( 'core/editor' ).getEditedPostAttribute( 'featured_media' ),
+			postTitle: select( editorStore ).getEditedPostAttribute( 'title' ),
+			postFeaturedMediaId: select( editorStore ).getEditedPostAttribute( 'featured_media' ),
+			isEditorPanelOpened:
+				select( editorStore ).isEditorPanelOpened ??
+				( select( 'core/edit-post' ) as EditorSelectors ).isEditorPanelOpened,
 		};
 	}, [] );
+
 	const { saveToMediaLibrary } = useSaveToMediaLibrary();
 	const { tracks } = useAnalytics();
 	const { recordEvent } = tracks;
@@ -69,7 +73,7 @@ export default function FeaturedImage( {
 	const { toggleEditorPanelOpened: toggleEditorPanelOpenedFromEditPost } =
 		useDispatch( 'core/edit-post' );
 	const { editPost, toggleEditorPanelOpened: toggleEditorPanelOpenedFromEditor } =
-		useDispatch( 'core/editor' );
+		useDispatch( editorStore );
 
 	// Get feature data
 	const { requireUpgrade, requestsCount, requestsLimit, currentTier, costs } = useAiFeature();
@@ -87,14 +91,6 @@ export default function FeaturedImage( {
 	// https://github.com/WordPress/gutenberg/blob/fe4d8cb936df52945c01c1863f7b87b58b7cc69f/packages/edit-post/CHANGELOG.md?plain=1#L19
 	const toggleEditorPanelOpened =
 		toggleEditorPanelOpenedFromEditor ?? toggleEditorPanelOpenedFromEditPost;
-	const isEditorPanelOpened = useSelect( select => {
-		const isOpened =
-			// eslint-disable-next-line @typescript-eslint/no-explicit-any
-			( select( 'core/editor' ) as any ).isEditorPanelOpened ??
-			// eslint-disable-next-line @typescript-eslint/no-explicit-any
-			( select( 'core/edit-post' ) as any ).isEditorPanelOpened;
-		return isOpened;
-	}, [] );
 
 	const {
 		pointer,
@@ -113,6 +109,7 @@ export default function FeaturedImage( {
 		cost: featuredImageCost,
 		type: 'featured-image-generation',
 		feature: FEATURED_IMAGE_FEATURE_NAME,
+		previousMediaId: postFeaturedMediaId,
 	} );
 
 	const handleModalClose = useCallback( () => {
@@ -202,7 +199,7 @@ export default function FeaturedImage( {
 				style: style,
 			} );
 
-			setCurrent( crrt => crrt + 1 );
+			setCurrent( () => images.length );
 			processImageGeneration( {
 				userPrompt,
 				postContent: postTitle + '\n\n' + postContent,
@@ -229,6 +226,7 @@ export default function FeaturedImage( {
 			postTitle,
 			postContent,
 			notEnoughRequests,
+			images,
 		]
 	);
 
@@ -341,7 +339,7 @@ export default function FeaturedImage( {
 	const generateAgainText = __( 'Generate another image', 'jetpack' );
 	const generateText = __( 'Generate', 'jetpack' );
 
-	const hasContent = postContent || postTitle;
+	const hasContent = postContent || postTitle ? true : false;
 	const hasPrompt = hasContent ? prompt.length >= 0 : prompt.length >= 3;
 	const disableInput = notEnoughRequests || currentPointer?.generating || requireUpgrade;
 	const disableAction = disableInput || ( ! hasContent && ! hasPrompt );
@@ -361,7 +359,11 @@ export default function FeaturedImage( {
 		<Button
 			onClick={ handleAccept }
 			variant="primary"
-			disabled={ ! currentImage?.image || currentImage?.generating }
+			disabled={
+				! currentImage?.image ||
+				currentImage?.generating ||
+				currentImage?.libraryId === postFeaturedMediaId
+			}
 		>
 			{ __( 'Set as featured image', 'jetpack' ) }
 		</Button>
@@ -385,7 +387,7 @@ export default function FeaturedImage( {
 			) }
 			<AiImageModal
 				postContent={ hasContent }
-				autoStart={ hasContent && ! postFeaturedMedia }
+				autoStart={ hasContent && ! postFeaturedMediaId }
 				autoStartAction={ handleFirstGenerate }
 				images={ images }
 				currentIndex={ current }
@@ -395,7 +397,9 @@ export default function FeaturedImage( {
 				placement={ placement }
 				onClose={ handleModalClose }
 				onTryAgain={ handleTryAgain }
-				onGenerate={ pointer?.current > 0 ? handleRegenerate : handleGenerate }
+				onGenerate={
+					pointer?.current > 0 || postFeaturedMediaId ? handleRegenerate : handleGenerate
+				}
 				generating={ currentPointer?.generating }
 				notEnoughRequests={ notEnoughRequests }
 				requireUpgrade={ requireUpgrade }
diff --git a/projects/plugins/jetpack/extensions/plugins/ai-assistant-plugin/components/ai-image/hooks/use-ai-image.ts b/projects/plugins/jetpack/extensions/plugins/ai-assistant-plugin/components/ai-image/hooks/use-ai-image.ts
index bd2fcdd96695a..0edcb0176663b 100644
--- a/projects/plugins/jetpack/extensions/plugins/ai-assistant-plugin/components/ai-image/hooks/use-ai-image.ts
+++ b/projects/plugins/jetpack/extensions/plugins/ai-assistant-plugin/components/ai-image/hooks/use-ai-image.ts
@@ -7,8 +7,8 @@ import {
 	ImageStyle,
 	askQuestionSync,
 } from '@automattic/jetpack-ai-client';
-import { useDispatch } from '@wordpress/data';
-import { useCallback, useRef, useState } from '@wordpress/element';
+import { useDispatch, useSelect } from '@wordpress/data';
+import { useCallback, useEffect, useRef, useState } from '@wordpress/element';
 import { __ } from '@wordpress/i18n';
 import { cleanForSlug } from '@wordpress/url';
 /**
@@ -19,7 +19,7 @@ import useSaveToMediaLibrary from '../../../hooks/use-save-to-media-library';
 /**
  * Types
  */
-import { FEATURED_IMAGE_FEATURE_NAME, GENERAL_IMAGE_FEATURE_NAME } from '../types';
+import { CoreSelectors, FEATURED_IMAGE_FEATURE_NAME, GENERAL_IMAGE_FEATURE_NAME } from '../types';
 import type { CarrouselImageData, CarrouselImages } from '../components/carrousel';
 import type { RoleType } from '@automattic/jetpack-ai-client';
 import type { FeatureControl } from 'extensions/store/wordpress-com/types.js';
@@ -42,11 +42,13 @@ export default function useAiImage( {
 	type,
 	cost,
 	autoStart = true,
+	previousMediaId,
 }: {
 	feature: AiImageFeature;
 	type: AiImageType;
 	cost: number;
 	autoStart?: boolean;
+	previousMediaId?: number;
 } ) {
 	const { generateImageWithParameters } = useImageGenerator();
 	const { increaseRequestsCount, featuresControl } = useAiFeature();
@@ -54,7 +56,10 @@ export default function useAiImage( {
 	const { createNotice } = useDispatch( 'core/notices' );
 
 	/* Images Control */
+	// pointer keeps track of request/generation iteration
 	const pointer = useRef( 0 );
+	// and current keeps track of what is the image exposed at the moment
+	// TODO: should current be any relevant here? It's just modal/carrousel logic after all
 	const [ current, setCurrent ] = useState( 0 );
 	const [ images, setImages ] = useState< CarrouselImages >( [ { generating: autoStart } ] );
 
@@ -75,6 +80,25 @@ export default function useAiImage( {
 		} );
 	}, [] );
 
+	// the selec/useEffect combo...
+	const loadedMedia = useSelect(
+		( select: ( store ) => CoreSelectors ) => select( 'core' )?.getMedia?.( previousMediaId ),
+		[ previousMediaId ]
+	);
+	useEffect( () => {
+		if ( loadedMedia ) {
+			updateImages(
+				{
+					image: loadedMedia.source_url,
+					libraryId: loadedMedia.id,
+					libraryUrl: loadedMedia.source_url,
+					generating: false,
+				},
+				pointer.current
+			);
+		}
+	}, [ loadedMedia, updateImages ] );
+
 	/*
 	 * Function to show a snackbar notice on the editor.
 	 */
@@ -123,6 +147,9 @@ export default function useAiImage( {
 			style?: string;
 		} ) => {
 			return new Promise< ImageResponse >( ( resolve, reject ) => {
+				if ( previousMediaId && pointer.current === 0 ) {
+					pointer.current++;
+				}
 				updateImages( { generating: true, error: null }, pointer.current );
 
 				// Ensure the site has enough requests to generate the image.
@@ -208,12 +235,13 @@ export default function useAiImage( {
 			saveToMediaLibrary,
 			showSnackbarNotice,
 			getImageNameSuggestion,
+			previousMediaId,
 		]
 	);
 
 	const handlePreviousImage = useCallback( () => {
 		setCurrent( Math.max( current - 1, 0 ) );
-	}, [ current, setCurrent ] );
+	}, [ current ] );
 
 	const handleNextImage = useCallback( () => {
 		setCurrent( Math.min( current + 1, images.length - 1 ) );
diff --git a/projects/plugins/jetpack/extensions/plugins/ai-assistant-plugin/components/ai-image/types.ts b/projects/plugins/jetpack/extensions/plugins/ai-assistant-plugin/components/ai-image/types.ts
index f0c0c5ae3d125..77f688f7dd94a 100644
--- a/projects/plugins/jetpack/extensions/plugins/ai-assistant-plugin/components/ai-image/types.ts
+++ b/projects/plugins/jetpack/extensions/plugins/ai-assistant-plugin/components/ai-image/types.ts
@@ -4,3 +4,16 @@ export const IMAGE_GENERATION_MODEL_STABLE_DIFFUSION = 'stable-diffusion' as con
 export const IMAGE_GENERATION_MODEL_DALL_E_3 = 'dall-e-3' as const;
 export const PLACEMENT_MEDIA_SOURCE_DROPDOWN = 'media-source-dropdown' as const;
 export const PLACEMENT_BLOCK_PLACEHOLDER_BUTTON = 'block-placeholder-button' as const;
+
+export interface EditorSelectors {
+	// actually getEditedPostAttribute can bring different values, but for our current use, number is fine (media ID)
+	getEditedPostAttribute: ( attribute: string ) => number;
+	isEditorPanelOpened: ( panel: string ) => boolean;
+}
+
+export interface CoreSelectors {
+	getMedia: ( mediaId: number ) => {
+		id: number;
+		source_url: string;
+	} | null;
+}