diff --git a/ts/editor/ImageHandle.svelte b/ts/editor/ImageHandle.svelte
index 40d2f6d72..f96250a54 100644
--- a/ts/editor/ImageHandle.svelte
+++ b/ts/editor/ImageHandle.svelte
@@ -2,33 +2,25 @@
 Copyright: Ankitects Pty Ltd and contributors
 License: GNU AGPL, version 3 or later; http://www.gnu.org/licenses/agpl.html
 -->
-<script lang="typescript">
+<script lang="ts">
     import ImageHandleFloat from "./ImageHandleFloat.svelte";
     import ImageHandleSizeSelect from "./ImageHandleSizeSelect.svelte";
 
     import { onDestroy, getContext } from "svelte";
     import { nightModeKey } from "components/context-keys";
 
-    export let image: HTMLImageElement | null = null;
-    export let imageRule: CSSStyleRule | null = null;
+    export let container: HTMLElement;
+    export let sheet: CSSStyleSheet;
+    export let activeImage: HTMLImageElement | null = null;
     export let isRtl: boolean = false;
 
-    export let container: HTMLElement;
-
-    $: selector = `:not([src="${image?.getAttribute("src")}"])`;
-    $: naturalWidth = image?.naturalWidth;
-    $: naturalHeight = image?.naturalHeight;
+    $: naturalWidth = activeImage?.naturalWidth;
+    $: naturalHeight = activeImage?.naturalHeight;
     $: aspectRatio = naturalWidth && naturalHeight ? naturalWidth / naturalHeight : NaN;
 
-    $: showDimensions = image
-        ? parseInt(getComputedStyle(image).getPropertyValue("height")) >= 50
-        : false;
+    $: showDimensions = activeImage ? Number(activeImage!.height) >= 50 : false;
 
-    $: showFloat = image
-        ? parseInt(getComputedStyle(image).getPropertyValue("width")) >= 100
-        : false;
-
-    $: active = imageRule?.selectorText.includes(selector) as boolean;
+    $: showFloat = activeImage ? Number(activeImage!.width) >= 100 : false;
 
     let actualWidth = "";
     let actualHeight = "";
@@ -42,39 +34,48 @@ License: GNU AGPL, version 3 or later; http://www.gnu.org/licenses/agpl.html
     let width = 0;
     let height = 0;
 
-    $: if (image) {
+    $: if (activeImage) {
         updateSizes();
+    } else {
+        resetSizes();
     }
 
-    const observer = new ResizeObserver(() => {
-        if (image) {
+    const resizeObserver = new ResizeObserver(() => {
+        if (activeImage) {
             updateSizes();
         }
     });
 
     function startObserving() {
-        observer.observe(container);
+        resizeObserver.observe(container);
     }
 
     function stopObserving() {
-        observer.unobserve(container);
+        resizeObserver.unobserve(container);
     }
 
     startObserving();
 
+    function resetSizes() {
+        top = 0;
+        left = 0;
+        width = 0;
+        height = 0;
+    }
+
     function updateSizes() {
         const containerRect = container.getBoundingClientRect();
-        const imageRect = image!.getBoundingClientRect();
+        const imageRect = activeImage!.getBoundingClientRect();
 
         containerTop = containerRect.top;
         containerLeft = containerRect.left;
         top = imageRect!.top - containerTop;
         left = imageRect!.left - containerLeft;
-        width = image!.clientWidth;
-        height = image!.clientHeight;
+        width = activeImage!.clientWidth;
+        height = activeImage!.clientHeight;
 
         /* we do not want the actual width, but rather the intended display width */
-        const widthProperty = image!.style.width;
+        const widthProperty = activeImage!.style.width;
         let inPixel = false;
         customDimensions = false;
 
@@ -91,7 +92,7 @@ License: GNU AGPL, version 3 or later; http://www.gnu.org/licenses/agpl.html
             actualWidth = String(naturalWidth);
         }
 
-        const heightProperty = image!.style.height;
+        const heightProperty = activeImage!.style.height;
         if (inPixel || heightProperty === "auto") {
             actualHeight = String(Math.trunc(Number(actualWidth) / aspectRatio));
         } else if (heightProperty) {
@@ -104,14 +105,43 @@ License: GNU AGPL, version 3 or later; http://www.gnu.org/licenses/agpl.html
         }
     }
 
-    function setPointerCapture(event: PointerEvent): void {
-        if (!active || event.pointerId !== 1) {
-            return;
-        }
+    /* memoized position of image on resize start
+     * prevents frantic behavior when image shift into the next/previous line */
+    let getDragWidth: (event: PointerEvent) => number;
+    let getDragHeight: (event: PointerEvent) => number;
 
-        stopObserving();
-        (event.target as Element).setPointerCapture(event.pointerId);
-    }
+    const setPointerCapture =
+        (north: boolean, west: boolean) =>
+        (event: PointerEvent): void => {
+            if (!active || event.pointerId !== 1) {
+                return;
+            }
+
+            const containerRect = container.getBoundingClientRect();
+            const imageRect = activeImage!.getBoundingClientRect();
+
+            const originalContainerY = containerRect.top;
+            const originalContainerX = containerRect.left;
+            const originalY = imageRect!.top - containerTop;
+            const originalX = imageRect!.left - containerLeft;
+
+            getDragWidth = (event) =>
+                west
+                    ? activeImage!.clientWidth -
+                      event.clientX +
+                      (originalContainerX + originalX)
+                    : event.clientX - originalContainerX - originalX;
+
+            getDragHeight = (event) =>
+                north
+                    ? activeImage!.clientHeight -
+                      event.clientY +
+                      (originalContainerY + originalY)
+                    : event.clientY - originalContainerY - originalY;
+
+            stopObserving();
+            (event.target as Element).setPointerCapture(event.pointerId);
+        };
 
     function resize(event: PointerEvent): void {
         const element = event.target! as Element;
@@ -120,8 +150,8 @@ License: GNU AGPL, version 3 or later; http://www.gnu.org/licenses/agpl.html
             return;
         }
 
-        const dragWidth = event.clientX - containerLeft - left;
-        const dragHeight = event.clientY - containerTop - top;
+        const dragWidth = getDragWidth(event);
+        const dragHeight = getDragHeight(event);
 
         const widthIncrease = dragWidth / naturalWidth!;
         const heightIncrease = dragHeight / naturalHeight!;
@@ -137,11 +167,11 @@ License: GNU AGPL, version 3 or later; http://www.gnu.org/licenses/agpl.html
         showDimensions = height >= 50;
         showFloat = width >= 100;
 
-        image!.style.width = `${width}px`;
-        image!.style.removeProperty("height");
+        activeImage!.width = width;
     }
 
     let sizeSelect: any;
+    let active = false;
 
     function onDblclick() {
         sizeSelect.toggleActualSize();
@@ -149,35 +179,26 @@ License: GNU AGPL, version 3 or later; http://www.gnu.org/licenses/agpl.html
 
     const nightMode = getContext(nightModeKey);
 
-    onDestroy(() => observer.disconnect());
+    onDestroy(() => resizeObserver.disconnect());
 </script>
 
-{#if image && imageRule}
-    <div
-        style="--top: {top}px; --left: {left}px; --width: {width}px; --height: {height}px;"
-        class="image-handle-selection"
-    >
+<div
+    style="--top: {top}px; --left: {left}px; --width: {width}px; --height: {height}px;"
+    class="image-handle-selection"
+>
+    {#if activeImage}
         <div
             class="image-handle-bg"
             on:mousedown|preventDefault
             on:dblclick={onDblclick}
         />
+
         {#if showFloat}
-            <div class="image-handle-float" class:is-rtl={isRtl}>
-                <ImageHandleFloat {isRtl} bind:float={image.style.float} />
+            <div class="image-handle-float" class:is-rtl={isRtl} on:click={updateSizes}>
+                <ImageHandleFloat {activeImage} {isRtl} />
             </div>
         {/if}
-        <div class="image-handle-size-select" class:is-rtl={isRtl}>
-            <ImageHandleSizeSelect
-                bind:this={sizeSelect}
-                bind:active
-                {image}
-                {imageRule}
-                {selector}
-                {isRtl}
-                on:update={updateSizes}
-            />
-        </div>
+
         {#if showDimensions}
             <div class="image-handle-dimensions" class:is-rtl={isRtl}>
                 <span>{actualWidth}&times;{actualHeight}</span>
@@ -186,22 +207,47 @@ License: GNU AGPL, version 3 or later; http://www.gnu.org/licenses/agpl.html
                     >{/if}
             </div>
         {/if}
+    {/if}
+
+    {#if sheet}
+        <div class="image-handle-size-select" class:is-rtl={isRtl}>
+            <ImageHandleSizeSelect
+                bind:this={sizeSelect}
+                bind:active
+                {container}
+                {sheet}
+                {activeImage}
+                {isRtl}
+                on:update={updateSizes}
+            />
+        </div>
+    {/if}
+
+    {#if activeImage}
         <div
             class:nightMode
+            class:active
             class="image-handle-control image-handle-control-nw"
             on:mousedown|preventDefault
+            on:pointerdown={setPointerCapture(true, true)}
+            on:pointerup={startObserving}
+            on:pointermove={resize}
         />
         <div
             class:nightMode
+            class:active
             class="image-handle-control image-handle-control-ne"
             on:mousedown|preventDefault
+            on:pointerdown={setPointerCapture(true, false)}
+            on:pointerup={startObserving}
+            on:pointermove={resize}
         />
         <div
             class:nightMode
             class:active
             class="image-handle-control image-handle-control-sw"
             on:mousedown|preventDefault
-            on:pointerdown={setPointerCapture}
+            on:pointerdown={setPointerCapture(false, true)}
             on:pointerup={startObserving}
             on:pointermove={resize}
         />
@@ -210,12 +256,12 @@ License: GNU AGPL, version 3 or later; http://www.gnu.org/licenses/agpl.html
             class:active
             class="image-handle-control image-handle-control-se"
             on:mousedown|preventDefault
-            on:pointerdown={setPointerCapture}
+            on:pointerdown={setPointerCapture(false, false)}
             on:pointerup={startObserving}
             on:pointermove={resize}
         />
-    </div>
-{/if}
+    {/if}
+</div>
 
 <style lang="scss">
     div {
@@ -301,6 +347,10 @@ License: GNU AGPL, version 3 or later; http://www.gnu.org/licenses/agpl.html
         left: -5px;
         border-bottom: none;
         border-right: none;
+
+        &.active {
+            cursor: nw-resize;
+        }
     }
 
     .image-handle-control-ne {
@@ -308,6 +358,10 @@ License: GNU AGPL, version 3 or later; http://www.gnu.org/licenses/agpl.html
         right: -5px;
         border-bottom: none;
         border-left: none;
+
+        &.active {
+            cursor: ne-resize;
+        }
     }
 
     .image-handle-control-sw {
diff --git a/ts/editor/ImageHandleFloat.svelte b/ts/editor/ImageHandleFloat.svelte
index 8a6bc50f8..bf000d7de 100644
--- a/ts/editor/ImageHandleFloat.svelte
+++ b/ts/editor/ImageHandleFloat.svelte
@@ -11,7 +11,7 @@ License: GNU AGPL, version 3 or later; http://www.gnu.org/licenses/agpl.html
 
     import { floatNoneIcon, floatLeftIcon, floatRightIcon } from "./icons";
 
-    export let float: string;
+    export let activeImage: HTMLImageElement;
     export let isRtl: boolean;
 
     const leftValues = {
@@ -33,18 +33,20 @@ License: GNU AGPL, version 3 or later; http://www.gnu.org/licenses/agpl.html
     <ButtonGroupItem>
         <IconButton
             tooltip={tr.editingFloatNone()}
-            active={float === "" || float === "none"}
+            active={activeImage.style.float === "" ||
+                activeImage.style.float === "none"}
             flipX={isRtl}
-            on:click={() => (float = "")}>{@html floatNoneIcon}</IconButton
+            on:click={() => (activeImage.style.float = "")}
+            >{@html floatNoneIcon}</IconButton
         >
     </ButtonGroupItem>
 
     <ButtonGroupItem>
         <IconButton
             tooltip={inlineStart.label}
-            active={float === inlineStart.position}
+            active={activeImage.style.float === inlineStart.position}
             flipX={isRtl}
-            on:click={() => (float = inlineStart.position)}
+            on:click={() => (activeImage.style.float = inlineStart.position)}
             >{@html floatLeftIcon}</IconButton
         >
     </ButtonGroupItem>
@@ -52,9 +54,9 @@ License: GNU AGPL, version 3 or later; http://www.gnu.org/licenses/agpl.html
     <ButtonGroupItem>
         <IconButton
             tooltip={inlineEnd.label}
-            active={float === inlineEnd.position}
+            active={activeImage.style.float === inlineEnd.position}
             flipX={isRtl}
-            on:click={() => (float = inlineEnd.position)}
+            on:click={() => (activeImage.style.float = inlineEnd.position)}
             >{@html floatRightIcon}</IconButton
         >
     </ButtonGroupItem>
diff --git a/ts/editor/ImageHandleSizeSelect.svelte b/ts/editor/ImageHandleSizeSelect.svelte
index b14f4124a..c95de0bd5 100644
--- a/ts/editor/ImageHandleSizeSelect.svelte
+++ b/ts/editor/ImageHandleSizeSelect.svelte
@@ -9,43 +9,184 @@ License: GNU AGPL, version 3 or later; http://www.gnu.org/licenses/agpl.html
     import ButtonGroupItem from "components/ButtonGroupItem.svelte";
     import IconButton from "components/IconButton.svelte";
 
-    import { createEventDispatcher } from "svelte";
+    import { createEventDispatcher, onDestroy } from "svelte";
     import { sizeActual, sizeMinimized } from "./icons";
+    import { nodeIsElement } from "./helpers";
+
+    export let container: HTMLElement;
+    export let sheet: CSSStyleSheet;
+
+    export let activeImage: HTMLImageElement | null;
+    export let active: boolean = false;
 
-    export let image: HTMLImageElement;
-    export let imageRule: CSSStyleRule;
-    export let selector: string;
-    export let active: boolean;
     export let isRtl: boolean;
+    export let maxWidth = 250;
+    export let maxHeight = 125;
 
     $: icon = active ? sizeActual : sizeMinimized;
 
     const dispatch = createEventDispatcher();
 
-    export function toggleActualSize() {
-        if (!image.hasAttribute("src")) {
+    function createPathRecursive(tokens: string[], element: Element): string[] {
+        const tagName = element.tagName.toLowerCase();
+
+        if (!element.parentElement) {
+            const nth =
+                Array.prototype.indexOf.call(
+                    (element.parentNode! as Document | ShadowRoot).children,
+                    element
+                ) + 1;
+            return [`${tagName}:nth-child(${nth})`, ...tokens];
+        } else {
+            const nth =
+                Array.prototype.indexOf.call(element.parentElement.children, element) +
+                1;
+            return createPathRecursive(
+                [`${tagName}:nth-child(${nth})`, ...tokens],
+                element.parentElement
+            );
+        }
+    }
+
+    function createPath(element: Element): string {
+        return createPathRecursive([], element).join(" > ");
+    }
+
+    let images: HTMLImageElement[] = [];
+
+    $: for (const [index, image] of images.entries()) {
+        const rule = sheet.cssRules[index] as CSSStyleRule;
+        rule.selectorText = createPath(image);
+    }
+
+    function filterImages(nodes: HTMLCollection | Node[]): HTMLImageElement[] {
+        const result: HTMLImageElement[] = [];
+
+        for (const node of nodes) {
+            if (!nodeIsElement(node)) {
+                continue;
+            }
+
+            if (node.tagName === "IMG") {
+                result.push(node as HTMLImageElement);
+            } else {
+                result.push(...filterImages(node.children));
+            }
+        }
+
+        return result;
+    }
+
+    function setImageRule(image: HTMLImageElement, rule: CSSStyleRule): void {
+        const width = Number(image.getAttribute("width")) | image.width;
+
+        rule.style.setProperty(
+            "width",
+            width < maxWidth ? `${width}px` : "auto",
+            "important"
+        );
+        rule.style.setProperty("height", "auto", "important");
+        rule.style.setProperty("max-width", `min(${maxWidth}px, 100%)`, "important");
+        rule.style.setProperty("max-height", `${maxHeight}px`, "important");
+    }
+
+    function resetImageRule(rule: CSSStyleRule): void {
+        rule.style.removeProperty("width");
+        rule.style.removeProperty("height");
+        rule.style.removeProperty("max-width");
+        rule.style.removeProperty("max-height");
+    }
+
+    function addImage(image: HTMLImageElement): void {
+        if (!container.contains(image)) {
             return;
         }
 
-        if (active) {
-            imageRule.selectorText = imageRule.selectorText.replace(selector, "");
-            active = false;
+        images.push(image);
+        const index = sheet.insertRule(
+            `${createPath(image)} {}`,
+            sheet.cssRules.length
+        );
+        const rule = sheet.cssRules[index] as CSSStyleRule;
+        setImageRule(image, rule);
+
+        images = images;
+    }
+
+    function addImageOnLoad(image: HTMLImageElement): void {
+        if (image.complete && image.naturalWidth !== 0 && image.naturalHeight !== 0) {
+            addImage(image);
         } else {
-            imageRule.selectorText += selector;
-            active = true;
+            image.addEventListener("load", () => {
+                addImage(image);
+            });
+        }
+    }
+
+    function removeImage(image: HTMLImageElement): void {
+        const index = images.indexOf(image);
+        if (index < 0) {
+            return;
+        }
+
+        images.splice(index, 1);
+        sheet.deleteRule(index);
+    }
+
+    const mutationObserver = new MutationObserver((mutations) => {
+        const addedImages = mutations.flatMap((mutation) =>
+            filterImages([...mutation.addedNodes])
+        );
+
+        for (const image of addedImages) {
+            addImageOnLoad(image);
+        }
+
+        const removedImages = mutations.flatMap((mutation) =>
+            filterImages([...mutation.removedNodes])
+        );
+
+        for (const image of removedImages) {
+            removeImage(image);
+        }
+
+        images = images;
+    });
+
+    $: if (container) {
+        mutationObserver.observe(container, { childList: true, subtree: true });
+    }
+
+    export function toggleActualSize() {
+        const index = images.indexOf(activeImage!);
+        if (index === -1) {
+            return;
+        }
+
+        const rule = sheet.cssRules[index] as CSSStyleRule;
+        active = !active;
+
+        if (active) {
+            resetImageRule(rule);
+        } else {
+            setImageRule(activeImage!, rule);
         }
 
         dispatch("update", active);
     }
+
+    onDestroy(() => mutationObserver.disconnect());
 </script>
 
-<ButtonGroup size={1.6}>
-    <ButtonGroupItem>
-        <IconButton
-            {active}
-            flipX={isRtl}
-            tooltip={tr.editingActualSize()}
-            on:click={toggleActualSize}>{@html icon}</IconButton
-        >
-    </ButtonGroupItem>
-</ButtonGroup>
+{#if activeImage}
+    <ButtonGroup size={1.6}>
+        <ButtonGroupItem>
+            <IconButton
+                {active}
+                flipX={isRtl}
+                tooltip={tr.editingActualSize()}
+                on:click={toggleActualSize}>{@html icon}</IconButton
+            >
+        </ButtonGroupItem>
+    </ButtonGroup>
+{/if}
diff --git a/ts/editor/editable-container.ts b/ts/editor/editable-container.ts
index 18a76dc07..3448e662e 100644
--- a/ts/editor/editable-container.ts
+++ b/ts/editor/editable-container.ts
@@ -8,7 +8,7 @@
 export class EditableContainer extends HTMLDivElement {
     baseStyle: HTMLStyleElement;
     baseRule?: CSSStyleRule;
-    imageRule?: CSSStyleRule;
+    imageStyle?: HTMLStyleElement;
 
     constructor() {
         super();
@@ -25,6 +25,7 @@ export class EditableContainer extends HTMLDivElement {
 
         this.baseStyle = document.createElement("style");
         this.baseStyle.setAttribute("rel", "stylesheet");
+        this.baseStyle.id = "baseStyle";
         shadow.appendChild(this.baseStyle);
     }
 
@@ -32,11 +33,6 @@ export class EditableContainer extends HTMLDivElement {
         const sheet = this.baseStyle.sheet as CSSStyleSheet;
         const baseIndex = sheet.insertRule("anki-editable {}");
         this.baseRule = sheet.cssRules[baseIndex] as CSSStyleRule;
-
-        const imageIndex = sheet.insertRule("anki-editable img {}");
-        this.imageRule = sheet.cssRules[imageIndex] as CSSStyleRule;
-        this.imageRule.style.setProperty("max-width", "min(250px, 100%)", "important");
-        this.imageRule.style.setProperty("max-height", "200px", "important");
     }
 
     initialize(color: string): void {
diff --git a/ts/editor/editing-area.ts b/ts/editor/editing-area.ts
index f0b44fadd..f13e22275 100644
--- a/ts/editor/editing-area.ts
+++ b/ts/editor/editing-area.ts
@@ -23,7 +23,7 @@ function onCutOrCopy(): void {
 }
 
 export class EditingArea extends HTMLDivElement {
-    imageHandle: ImageHandle;
+    imageHandle: Promise<ImageHandle>;
     editableContainer: EditableContainer;
     editable: Editable;
     codable: Codable;
@@ -35,9 +35,12 @@ export class EditingArea extends HTMLDivElement {
         this.editableContainer = document.createElement("div", {
             is: "anki-editable-container",
         }) as EditableContainer;
+
+        const imageStyle = document.createElement("style");
+        imageStyle.setAttribute("rel", "stylesheet");
+        imageStyle.id = "imageHandleStyle";
+
         this.editable = document.createElement("anki-editable") as Editable;
-        this.editableContainer.shadowRoot!.appendChild(this.editable);
-        this.appendChild(this.editableContainer);
 
         const context = new Map();
         context.set(
@@ -45,14 +48,28 @@ export class EditingArea extends HTMLDivElement {
             document.documentElement.classList.contains("night-mode")
         );
 
-        this.imageHandle = new ImageHandle({
-            target: this,
-            anchor: this.editableContainer,
-            props: {
-                container: this.editable,
-            },
-            context,
-        } as any);
+        let imageHandleResolve: (value: ImageHandle) => void;
+        this.imageHandle = new Promise<ImageHandle>((resolve) => {
+            imageHandleResolve = resolve;
+        });
+
+        imageStyle.addEventListener("load", () =>
+            imageHandleResolve(
+                new ImageHandle({
+                    target: this,
+                    anchor: this.editableContainer,
+                    props: {
+                        container: this.editable,
+                        sheet: imageStyle.sheet,
+                    },
+                    context,
+                } as any)
+            )
+        );
+
+        this.editableContainer.shadowRoot!.appendChild(imageStyle);
+        this.editableContainer.shadowRoot!.appendChild(this.editable);
+        this.appendChild(this.editableContainer);
 
         this.codable = document.createElement("textarea", {
             is: "anki-codable",
@@ -75,7 +92,7 @@ export class EditingArea extends HTMLDivElement {
     }
 
     set fieldHTML(content: string) {
-        this.activeInput.fieldHTML = content;
+        this.imageHandle.then(() => (this.activeInput.fieldHTML = content));
     }
 
     get fieldHTML(): string {
@@ -186,19 +203,21 @@ export class EditingArea extends HTMLDivElement {
     }
 
     resetImageHandle(): void {
-        (this.imageHandle as any).$set({
-            image: null,
-            imageRule: null,
-        });
+        this.imageHandle.then((imageHandle) =>
+            (imageHandle as any).$set({
+                activeImage: null,
+            })
+        );
     }
 
     showImageHandle(event: MouseEvent): void {
         if (event.target instanceof HTMLImageElement) {
-            (this.imageHandle as any).$set({
-                image: event.target,
-                imageRule: this.editableContainer.imageRule,
-                isRtl: this.isRightToLeft(),
-            });
+            this.imageHandle.then((imageHandle) =>
+                (imageHandle as any).$set({
+                    activeImage: event.target,
+                    isRtl: this.isRightToLeft(),
+                })
+            );
         } else {
             this.resetImageHandle();
         }
@@ -211,6 +230,7 @@ export class EditingArea extends HTMLDivElement {
             this.fieldHTML = this.codable.teardown();
             this.editable.hidden = false;
         } else {
+            this.resetImageHandle();
             this.editable.hidden = true;
             this.codable.setup(this.editable.fieldHTML);
         }