diff --git a/.changeset/calm-images-select.md b/.changeset/calm-images-select.md
new file mode 100644
index 0000000000..a2de4d4126
--- /dev/null
+++ b/.changeset/calm-images-select.md
@@ -0,0 +1,5 @@
+---
+"@emdash-cms/admin": patch
+---
+
+Fixes image action controls intermittently failing to appear when selecting an image in the editor.
diff --git a/packages/admin/src/components/editor/ImageNode.tsx b/packages/admin/src/components/editor/ImageNode.tsx
index a1331ff837..1663ca21b0 100644
--- a/packages/admin/src/components/editor/ImageNode.tsx
+++ b/packages/admin/src/components/editor/ImageNode.tsx
@@ -47,7 +47,14 @@ declare module "@tiptap/react" {
 }
 
 // React component for the image node view
-function ImageNodeView({ node, updateAttributes, selected, deleteNode, editor }: NodeViewProps) {
+function ImageNodeView({
+	node,
+	updateAttributes,
+	selected,
+	deleteNode,
+	editor,
+	getPos,
+}: NodeViewProps) {
 	const { t } = useLingui();
 	const [isEditingAlt, setIsEditingAlt] = React.useState(false);
 	const [altText, setAltText] = React.useState(node.attrs.alt || "");
@@ -75,6 +82,14 @@ function ImageNodeView({ node, updateAttributes, selected, deleteNode, editor }:
 		setAltText(node.attrs.alt || "");
 	}, [node.attrs.alt]);
 
+	const handlePointerDown = (event: React.PointerEvent) => {
+		if (!editor.isEditable || !event.isPrimary || event.button !== 0) return;
+		const position = getPos();
+		if (typeof position === "number") {
+			editor.commands.setNodeSelection(position);
+		}
+	};
+
 	const getImageAttrs = (): ImageAttributes => ({
 		src: node.attrs.src,
 		alt: node.attrs.alt,
@@ -165,10 +180,8 @@ function ImageNodeView({ node, updateAttributes, selected, deleteNode, editor }:
 	return (
 		<NodeViewWrapper
 			style={alignmentStyle}
-			className={cn(
-				"relative my-4 group",
-				selected && "ring-2 ring-kumo-brand ring-offset-2 rounded-lg",
-			)}
+			onPointerDown={handlePointerDown}
+			className={cn("relative my-4", selected && "ring-2 ring-kumo-brand ring-offset-2 rounded-lg")}
 		>
 			<figure className="relative">
 				<img
@@ -185,7 +198,7 @@ function ImageNodeView({ node, updateAttributes, selected, deleteNode, editor }:
 
 				{/* Selection overlay with actions */}
 				{selected && (
-					<div className="absolute top-2 end-2 flex gap-1 opacity-0 group-hover:opacity-100 transition-opacity">
+					<div className="absolute top-2 end-2 flex gap-1">
 						<Button
 							type="button"
 							variant="secondary"
diff --git a/packages/admin/tests/editor/image-selection.test.tsx b/packages/admin/tests/editor/image-selection.test.tsx
new file mode 100644
index 0000000000..26be791784
--- /dev/null
+++ b/packages/admin/tests/editor/image-selection.test.tsx
@@ -0,0 +1,62 @@
+import { screen } from "@testing-library/react";
+import { useEditor, EditorContent } from "@tiptap/react";
+import StarterKit from "@tiptap/starter-kit";
+import * as React from "react";
+import { describe, it, expect } from "vitest";
+
+import { ImageExtension } from "../../src/components/editor/ImageNode.js";
+import { render } from "../utils/render.js";
+
+function TestEditor() {
+	const editor = useEditor({
+		extensions: [StarterKit, ImageExtension],
+		content: {
+			type: "doc",
+			content: [
+				{ type: "paragraph", content: [{ type: "text", text: "Before" }] },
+				{ type: "image", attrs: { src: "/img.jpg", alt: "Example" } },
+			],
+		},
+		immediatelyRender: true,
+	});
+
+	if (!editor) return null;
+	return <EditorContent editor={editor} />;
+}
+
+function pressWithPointerDrift(target: HTMLElement) {
+	const rect = target.getBoundingClientRect();
+	const clientX = rect.left + rect.width / 2;
+	const clientY = rect.top + rect.height / 2;
+	const pointer = {
+		bubbles: true,
+		button: 0,
+		buttons: 1,
+		clientX,
+		clientY,
+		isPrimary: true,
+		pointerId: 1,
+		pointerType: "mouse",
+	};
+
+	target.dispatchEvent(new PointerEvent("pointerdown", pointer));
+	target.dispatchEvent(new MouseEvent("mousedown", pointer));
+	document.dispatchEvent(new MouseEvent("mousemove", { ...pointer, clientX: clientX + 6 }));
+	target.dispatchEvent(
+		new PointerEvent("pointerup", { ...pointer, buttons: 0, clientX: clientX + 6 }),
+	);
+	target.dispatchEvent(new MouseEvent("mouseup", { ...pointer, buttons: 0, clientX: clientX + 6 }));
+}
+
+describe("Editor image selection", () => {
+	it("shows image actions after a primary press with slight pointer drift", async () => {
+		void render(<TestEditor />);
+		const image = await screen.findByRole("img", { name: "Example" });
+
+		expect(screen.queryByRole("button", { name: "Image settings" })).toBeNull();
+		pressWithPointerDrift(image);
+
+		const settings = await screen.findByRole("button", { name: "Image settings" });
+		expect(getComputedStyle(settings.parentElement!).opacity).toBe("1");
+	});
+});