diff --git a/src/lib/components/chat/ContentRenderer/FloatingButtons.svelte b/src/lib/components/chat/ContentRenderer/FloatingButtons.svelte
index e919bc57d4..a2119b2152 100644
--- a/src/lib/components/chat/ContentRenderer/FloatingButtons.svelte
+++ b/src/lib/components/chat/ContentRenderer/FloatingButtons.svelte
@@ -1,5 +1,6 @@
 <script lang="ts">
 	import { getContext, tick } from 'svelte';
+	import { positionSelectionToolbar } from '$lib/utils/selectionToolbar';
 	const i18n = getContext<typeof import('$lib/i18n').default>('i18n');
 
 	import ChatBubble from '$lib/components/icons/ChatBubble.svelte';
@@ -7,6 +8,8 @@
 	import LightBulb from '$lib/components/icons/LightBulb.svelte';
 
 	export let id = '';
+	export let range: Range | null = null;
+	export let selectedText = '';
 	export let onComment: (() => void) | null = null;
 
 	export let actions = [];
@@ -15,7 +18,6 @@
 	let floatingInput = false;
 	let selectedAction = null;
 
-	let selectedText = '';
 	let floatingInputValue = '';
 
 	const portal = (node: HTMLElement) => {
@@ -86,7 +88,6 @@
 
 	export const closeHandler = () => {
 		selectedAction = null;
-		selectedText = '';
 		floatingInput = false;
 		floatingInputValue = '';
 	};
@@ -94,20 +95,20 @@
 
 <div
 	use:portal
+	use:positionSelectionToolbar={range}
 	id={`floating-buttons-${id}`}
-	class="fixed rounded-lg mt-1 text-xs z-9999"
-	style="display: none"
+	class="fixed max-w-[calc(100vw-1rem)] rounded-lg text-xs z-9999"
+	style:display={range ? undefined : 'none'}
 >
 	{#if !floatingInput}
 		<div
-			class="flex flex-row shrink-0 p-0.5 bg-white dark:bg-gray-850 dark:text-gray-100 text-medium rounded-xl shadow-xl border border-gray-100 dark:border-gray-800"
+			class="flex flex-row flex-wrap shrink-0 p-0.5 bg-white dark:bg-gray-850 dark:text-gray-100 text-medium rounded-xl shadow-xl border border-gray-100 dark:border-gray-800"
 		>
 			{#each displayActions as action}
 				<button
 					aria-label={action.label}
-					class="px-1.5 py-[0.0625rem] hover:bg-gray-50 dark:hover:bg-gray-800 rounded-xl flex items-center gap-1 min-w-fit transition"
+					class="px-1.5 py-[0.0625rem] min-h-9 sm:min-h-0 hover:bg-gray-50 dark:hover:bg-gray-800 rounded-xl flex items-center gap-1 min-w-fit transition"
 					on:click={async () => {
-						selectedText = window.getSelection().toString();
 						selectedAction = action;
 
 						if (action.prompt.includes('{{INPUT_CONTENT}}')) {
@@ -135,7 +136,7 @@
 			{#if onComment}<button
 					type="button"
 					aria-label={$i18n.t('Comment')}
-					class="px-1.5 py-[0.0625rem] hover:bg-gray-50 dark:hover:bg-gray-800 rounded-xl flex items-center gap-1 min-w-fit transition"
+					class="px-1.5 py-[0.0625rem] min-h-9 sm:min-h-0 hover:bg-gray-50 dark:hover:bg-gray-800 rounded-xl flex items-center gap-1 min-w-fit transition"
 					on:mousedown|preventDefault
 					on:click={onComment}
 					><Annotation className="size-3 shrink-0" /><span>{$i18n.t('Comment')}</span></button
@@ -143,12 +144,12 @@
 		</div>
 	{:else}
 		<div
-			class="py-1 flex dark:text-gray-100 bg-white dark:bg-gray-850 border border-gray-100 dark:border-gray-800 w-72 rounded-full shadow-xl"
+			class="py-1 flex dark:text-gray-100 bg-white dark:bg-gray-850 border border-gray-100 dark:border-gray-800 w-72 max-w-full rounded-full shadow-xl"
 		>
 			<input
 				type="text"
 				id="floating-message-input"
-				class="ml-5 bg-transparent outline-hidden w-full flex-1 text-sm"
+				class="ml-5 min-w-0 bg-transparent outline-hidden w-full flex-1 text-sm"
 				placeholder={$i18n.t('Ask a question')}
 				aria-label={$i18n.t('Ask a question')}
 				bind:value={floatingInputValue}
diff --git a/src/lib/components/chat/FileNav.svelte b/src/lib/components/chat/FileNav.svelte
index e75de6c61b..bdf097d828 100644
--- a/src/lib/components/chat/FileNav.svelte
+++ b/src/lib/components/chat/FileNav.svelte
@@ -92,6 +92,7 @@
 	} | null = null;
 	// Keep typing from invalidating the keyed selection and remounting the input.
 	let fileAskInput = '';
+	let usingFileAsk = false;
 	let asking = false;
 	const positionFileAsk = (node: HTMLFormElement, anchor: Range | HTMLElement) => {
 		document.body.appendChild(node);
@@ -192,6 +193,7 @@
 		};
 	};
 	const captureSelection = () => {
+		if (!active || usingFileAsk) return;
 		const selection = window.getSelection();
 		if (!onAskFile || !openedFile || !selection?.rangeCount || selection.isCollapsed) return;
 		const range = selection.getRangeAt(0);
@@ -2014,6 +2016,13 @@
 	}}
 />
 
+<svelte:document
+	on:selectionchange={captureSelection}
+	on:focusin={(event) => {
+		usingFileAsk = !!(event.target as Element)?.closest('[data-file-ask]');
+	}}
+/>
+
 <svelte:window
 	on:keydown={(event) => {
 		if (!active) return;
@@ -2023,9 +2032,9 @@
 		} else handleKeydown(event);
 	}}
 	on:click={handleWindowClick}
-	on:pointerdown={(event) => {
-		if (fileAsk && !dirtyChoice && !(event.target as Element)?.closest('[data-file-ask]'))
-			fileAsk = null;
+	on:pointerdown|capture={(event) => {
+		usingFileAsk = !!(event.target as Element)?.closest('[data-file-ask]');
+		if (fileAsk && !dirtyChoice && !usingFileAsk) fileAsk = null;
 	}}
 />
 
@@ -2368,8 +2377,6 @@
 		<!-- Content -->
 		<div
 			bind:this={viewerRoot}
-			on:mouseup={captureSelection}
-			on:keyup={captureSelection}
 			class="flex-1 overflow-y-auto min-h-0 min-w-0"
 			on:click={(e) => {
 				closeDirectoryMenu();
diff --git a/src/lib/components/chat/Messages/ContentRenderer.svelte b/src/lib/components/chat/Messages/ContentRenderer.svelte
index 4627f6eab3..b1e6fcddda 100644
--- a/src/lib/components/chat/Messages/ContentRenderer.svelte
+++ b/src/lib/components/chat/Messages/ContentRenderer.svelte
@@ -105,9 +105,14 @@
 	export let onToolCallResolved = (e) => {};
 	export let onSetInputText = (text) => {};
 
+	/** @type {HTMLDivElement | undefined} */
 	let contentContainerElement;
+	/** @type {{ closeHandler: () => void } | undefined} */
 	let floatingButtonsElement;
+	/** @type {Range | null} */
 	let floatingButtonsRange = null;
+	let selectedText = '';
+	let usingFloatingButtons = false;
 
 	let sourceIds = [];
 	$: getSourceIds(sources);
@@ -192,65 +197,41 @@
 		}
 	);
 
-	const updateButtonPosition = (event) => {
-		const buttonsContainerElement = document.getElementById(`floating-buttons-${id}`);
+	const updateSelection = () => {
+		if (usingFloatingButtons) return;
+		const selection = window.getSelection();
+		const range = selection?.rangeCount ? selection.getRangeAt(0) : null;
 		if (
-			!contentContainerElement?.contains(event.target) &&
-			!buttonsContainerElement?.contains(event.target)
+			!selection ||
+			!range ||
+			!selection.toString().trim() ||
+			!contentContainerElement?.contains(range.startContainer) ||
+			!contentContainerElement.contains(range.endContainer)
 		) {
 			closeFloatingButtons();
 			return;
 		}
-
-		setTimeout(async () => {
-			await tick();
-
-			if (!contentContainerElement?.contains(event.target)) return;
-
-			let selection = window.getSelection();
-
-			if (selection.toString().trim().length > 0) {
-				floatingButtonsRange = selection.getRangeAt(0);
-				commentSelection = $config?.features?.enable_comments && $user ? selectedComment() : null;
-				positionFloatingButtons();
-			} else {
-				closeFloatingButtons();
-			}
-		}, 0);
+		floatingButtonsElement?.closeHandler();
+		selectedText = selection.toString();
+		floatingButtonsRange = range.cloneRange();
+		commentSelection = $config?.features?.enable_comments && $user ? selectedComment() : null;
 	};
 
-	const positionFloatingButtons = () => {
-		const buttonsContainerElement = document.getElementById(`floating-buttons-${id}`);
-		if (!floatingButtonsRange || !buttonsContainerElement) return;
-
-		const rect = floatingButtonsRange.getBoundingClientRect();
-		const parentRect = contentContainerElement.getBoundingClientRect();
-
-		buttonsContainerElement.style.display = 'block';
-
-		// Calculate space available on the right
-		const spaceOnRight = parentRect.right - rect.left;
-		let halfScreenWidth = $mobile ? window.innerWidth / 2 : window.innerWidth / 3;
-
-		if (spaceOnRight < halfScreenWidth) {
-			const right = document.documentElement.clientWidth - rect.right;
-			buttonsContainerElement.style.right = `${right}px`;
-			buttonsContainerElement.style.left = 'auto'; // Reset left
-		} else {
-			// Enough space, position using 'left'
-			buttonsContainerElement.style.left = `${rect.left}px`;
-			buttonsContainerElement.style.right = 'auto'; // Reset right
+	/** @param {Event} event */
+	const toolbarInteractionHandler = (event) => {
+		if (!(event.target instanceof Node)) return;
+		const toolbar = document.getElementById(`floating-buttons-${id}`);
+		// Keep the snapshot while a touch focuses an action or its question input.
+		usingFloatingButtons = !!toolbar?.contains(event.target);
+		if (!usingFloatingButtons && !contentContainerElement?.contains(event.target)) {
+			closeFloatingButtons();
 		}
-		buttonsContainerElement.style.top = `${rect.bottom + 5}px`; // +5 to add some spacing
 	};
 
 	const closeFloatingButtons = () => {
 		commentSelection = null;
 		floatingButtonsRange = null;
-		const buttonsContainerElement = document.getElementById(`floating-buttons-${id}`);
-		if (buttonsContainerElement) {
-			buttonsContainerElement.style.display = 'none';
-		}
+		selectedText = '';
 
 		if (floatingButtonsElement) {
 			// check if closeHandler is defined
@@ -274,8 +255,9 @@
 
 	function attachListeners() {
 		if (!listenersAttached && contentContainerElement) {
-			contentContainerElement.addEventListener('mouseup', updateButtonPosition);
-			document.addEventListener('mouseup', updateButtonPosition);
+			document.addEventListener('selectionchange', updateSelection);
+			document.addEventListener('pointerdown', toolbarInteractionHandler, true);
+			document.addEventListener('focusin', toolbarInteractionHandler, true);
 			document.addEventListener('keydown', keydownHandler);
 			listenersAttached = true;
 		}
@@ -283,8 +265,9 @@
 
 	function detachListeners() {
 		if (listenersAttached) {
-			contentContainerElement?.removeEventListener('mouseup', updateButtonPosition);
-			document.removeEventListener('mouseup', updateButtonPosition);
+			document.removeEventListener('selectionchange', updateSelection);
+			document.removeEventListener('pointerdown', toolbarInteractionHandler, true);
+			document.removeEventListener('focusin', toolbarInteractionHandler, true);
 			document.removeEventListener('keydown', keydownHandler);
 			listenersAttached = false;
 		}
@@ -301,8 +284,6 @@
 	});
 </script>
 
-<svelte:window on:scroll|capture={positionFloatingButtons} on:resize={positionFloatingButtons} />
-
 <div bind:this={contentContainerElement}>
 	{#if output?.length}
 		<StructuredOutputRenderer
@@ -408,6 +389,8 @@
 {#if floatingButtons}
 	<FloatingButtons
 		bind:this={floatingButtonsElement}
+		range={floatingButtonsRange}
+		{selectedText}
 		{id}
 		actions={$settings?.floatingActionButtons ?? []}
 		onComment={commentSelection
diff --git a/src/lib/components/comments/CommentsHost.svelte b/src/lib/components/comments/CommentsHost.svelte
index 352dba5bae..e1b486c67e 100644
--- a/src/lib/components/comments/CommentsHost.svelte
+++ b/src/lib/components/comments/CommentsHost.svelte
@@ -6,6 +6,7 @@
 	import CommentHighlights from './CommentHighlights.svelte';
 	import { selectedComment, commentSelectionDraft } from './anchors';
 	import { toast } from 'svelte-sonner';
+	import { positionSelectionToolbar } from '$lib/utils/selectionToolbar';
 	const i18n = getContext<any>('i18n');
 	let selection: ReturnType<typeof selectedComment> = null;
 	let account: string | null = null;
@@ -23,13 +24,15 @@
 		!$page.url.pathname.startsWith('/s/')
 	);
 	let preparing = false;
+	let selectionButton: HTMLButtonElement;
+	let usingSelectionButton = false;
 	$: if (($user?.id ?? null) !== account) {
 		account = $user?.id ?? null;
 		commentSelectionDraft.set(null);
 		selection = null;
 	}
 	const select = () => {
-		if (!preparing) selection = commentsAllowed ? selectedComment() : null;
+		if (!preparing && !usingSelectionButton) selection = commentsAllowed ? selectedComment() : null;
 	};
 	const commentSelection = async () => {
 		const selected = selection;
@@ -50,15 +53,21 @@
 		}
 	};
 	onMount(() => {
-		document.addEventListener('mouseup', select);
-		document.addEventListener('keyup', select);
+		document.addEventListener('selectionchange', select);
 		return () => {
-			document.removeEventListener('mouseup', select);
-			document.removeEventListener('keyup', select);
+			document.removeEventListener('selectionchange', select);
 		};
 	});
 </script>
 
+<svelte:document
+	on:focusin={(event) => {
+		usingSelectionButton = !!selectionButton?.contains(event.target as Node);
+	}}
+	on:pointerdown|capture={(event) => {
+		usingSelectionButton = !!selectionButton?.contains(event.target as Node);
+	}}
+/>
 <svelte:window
 	on:keydown={(event) => {
 		if (event.key === 'Escape') {
@@ -70,15 +79,15 @@
 			selection = null;
 		}
 	}}
-	on:scroll|capture={() => (selection = null)}
 />
 {#if commentsAllowed}
 	{#key account}<CommentHighlights />{/key}
 	{#if selection && !selection.options.toolbar_id}
 		<button
+			bind:this={selectionButton}
+			use:positionSelectionToolbar={selection.range}
 			type="button"
-			class="fixed z-9999 flex items-center gap-1 rounded-xl border border-gray-100 dark:border-gray-800 bg-white dark:bg-gray-850 px-2 py-1 text-xs shadow-xl"
-			style={`left:${Math.max(8, Math.min(selection.rect.left, window.innerWidth - 130))}px;top:${Math.min(window.innerHeight - 48, selection.rect.bottom + 12)}px`}
+			class="fixed z-9999 min-h-9 sm:min-h-0 flex items-center gap-1 rounded-xl border border-gray-100 dark:border-gray-800 bg-white dark:bg-gray-850 px-2 py-1 text-xs shadow-xl"
 			on:mousedown|preventDefault
 			disabled={preparing}
 			on:click={commentSelection}><Annotation className="size-3" />{$i18n.t('Comment')}</button
diff --git a/src/lib/components/comments/anchors.ts b/src/lib/components/comments/anchors.ts
index 69a4b411c5..95624981e2 100644
--- a/src/lib/components/comments/anchors.ts
+++ b/src/lib/components/comments/anchors.ts
@@ -147,7 +147,7 @@ export function selectedComment() {
 			source: sha256(text),
 			content_hash: options.content_hash
 		};
-		return { options, anchor, rect: range.getBoundingClientRect() };
+		return { options, anchor, range, rect: range.getBoundingClientRect() };
 	}
 	return null;
 }
diff --git a/src/lib/utils/selectionToolbar.ts b/src/lib/utils/selectionToolbar.ts
new file mode 100644
index 0000000000..ba78e89adb
--- /dev/null
+++ b/src/lib/utils/selectionToolbar.ts
@@ -0,0 +1,32 @@
+import { autoUpdate, computePosition, flip, offset, shift } from '@floating-ui/dom';
+
+// Range geometry follows scrolling; Floating UI also accounts for the on-screen keyboard.
+export function positionSelectionToolbar(node: HTMLElement, range: Range | null) {
+	let cleanup = () => {};
+	const update = (range: Range | null) => {
+		cleanup();
+		if (!range) return;
+		let active = true;
+		const reference = {
+			getBoundingClientRect: () => range.getBoundingClientRect(),
+			contextElement: range.commonAncestorContainer.parentElement ?? undefined
+		};
+		const stop = autoUpdate(reference, node, () => {
+			void computePosition(reference, node, {
+				strategy: 'fixed',
+				placement: 'bottom-start',
+				middleware: [offset(12), flip(), shift({ padding: 8 })]
+			}).then(({ x, y }) => {
+				if (!active) return;
+				node.style.left = `${x}px`;
+				node.style.top = `${y}px`;
+			});
+		});
+		cleanup = () => {
+			active = false;
+			stop();
+		};
+	};
+	update(range);
+	return { update, destroy: () => cleanup() };
+}