diff --git a/packages/frontend/editor-ui/src/features/ndv/parameters/components/ParameterInputFull.vue b/packages/frontend/editor-ui/src/features/ndv/parameters/components/ParameterInputFull.vue
index 6a17e80c60f..f5611ef0693 100644
--- a/packages/frontend/editor-ui/src/features/ndv/parameters/components/ParameterInputFull.vue
+++ b/packages/frontend/editor-ui/src/features/ndv/parameters/components/ParameterInputFull.vue
@@ -522,7 +522,14 @@ function removeOverride(clearField = false) {
 						@drop="onDrop"
 					>
 						<template v-if="showOverrideButton && isSingleLineInput" #overrideButton>
-							<FromAiOverrideButton @click="applyOverride" />
+							<FromAiOverrideButton
+								:size="
+									!isExpression && ['number', 'multiOptions'].includes(parameter.type)
+										? 'small'
+										: 'medium'
+								"
+								@click="applyOverride"
+							/>
 						</template>
 					</ParameterInputWrapper>
 				</div>
diff --git a/packages/frontend/editor-ui/src/features/ndv/parameters/components/ParameterInputOverrides/FromAiOverrideButton.vue b/packages/frontend/editor-ui/src/features/ndv/parameters/components/ParameterInputOverrides/FromAiOverrideButton.vue
index b314a9b15d3..ac57de1577e 100644
--- a/packages/frontend/editor-ui/src/features/ndv/parameters/components/ParameterInputOverrides/FromAiOverrideButton.vue
+++ b/packages/frontend/editor-ui/src/features/ndv/parameters/components/ParameterInputOverrides/FromAiOverrideButton.vue
@@ -8,8 +8,9 @@ const i18n = useI18n();
 withDefaults(
 	defineProps<{
 		position?: 'inline' | 'standalone';
+		size?: 'small' | 'medium';
 	}>(),
-	{ position: 'inline' },
+	{ position: 'inline', size: 'medium' },
 );
 
 const emit = defineEmits<{
@@ -24,7 +25,7 @@ const emit = defineEmits<{
 		</template>
 
 		<div
-			:class="[$style.overrideButton, $style[position]]"
+			:class="[$style.overrideButton, $style[position], $style[size]]"
 			data-test-id="from-ai-override-button"
 			@click="emit('click')"
 		>
@@ -38,8 +39,8 @@ const emit = defineEmits<{
 	display: flex;
 	align-items: center;
 	justify-content: center;
-	height: 30px;
-	width: 30px;
+	height: var(--from-ai-button-size);
+	width: var(--from-ai-button-size);
 	background-color: var(--color--foreground);
 	color: var(--color--foreground--shade-2);
 	cursor: pointer;
@@ -55,6 +56,14 @@ const emit = defineEmits<{
 	}
 }
 
+.small {
+	--from-ai-button-size: var(--height--sm);
+}
+
+.medium {
+	--from-ai-button-size: var(--height--md);
+}
+
 .inline {
 	border-left: 0;
 	border-top-right-radius: var(--radius);
diff --git a/packages/frontend/editor-ui/src/features/ndv/parameters/components/ResourceLocator/ResourceLocator.vue b/packages/frontend/editor-ui/src/features/ndv/parameters/components/ResourceLocator/ResourceLocator.vue
index bbcdd2ef264..6c21c6a0daa 100644
--- a/packages/frontend/editor-ui/src/features/ndv/parameters/components/ResourceLocator/ResourceLocator.vue
+++ b/packages/frontend/editor-ui/src/features/ndv/parameters/components/ResourceLocator/ResourceLocator.vue
@@ -1278,7 +1278,10 @@ function removeOverride() {
 									</template>
 								</N8nInput>
 								<div v-if="showOverrideButton" :class="$style.overrideButtonInline">
-									<FromAiOverrideButton @click="applyOverride" />
+									<FromAiOverrideButton
+										:size="isValueExpression || forceShowExpression ? 'medium' : 'small'"
+										@click="applyOverride"
+									/>
 								</div>
 							</div>
 						</template>
diff --git a/packages/quality/testing/playwright/pages/NodeDetailsViewPage.ts b/packages/quality/testing/playwright/pages/NodeDetailsViewPage.ts
index 6f1a94235e7..b87bba1f891 100644
--- a/packages/quality/testing/playwright/pages/NodeDetailsViewPage.ts
+++ b/packages/quality/testing/playwright/pages/NodeDetailsViewPage.ts
@@ -244,6 +244,22 @@ export class NodeDetailsViewPage extends BasePage {
 		return locatorByIndex(this.container.getByTestId(`parameter-input-${parameterName}`), index);
 	}
 
+	getParameterInputBorder(parameterName: string) {
+		return this.getParameterInput(parameterName).locator('.n8n-input__wrapper');
+	}
+
+	getParameterNumberBorder(parameterName: string) {
+		return this.getParameterInput(parameterName).getByTestId('input-number');
+	}
+
+	getParameterExpressionBorder(parameterName: string) {
+		return this.getParameterInput(parameterName).locator('.el-input-group__prepend').locator('..');
+	}
+
+	getFromAiOverrideButton(parameterName: string) {
+		return this.getParameterInput(parameterName).getByTestId('from-ai-override-button');
+	}
+
 	getParameterInputTextbox(parameterName: string, index?: number) {
 		return this.getParameterInput(parameterName, index).getByRole('textbox');
 	}
diff --git a/packages/quality/testing/playwright/tests/e2e/regression/ado-5599-from-ai-button-alignment.spec.ts b/packages/quality/testing/playwright/tests/e2e/regression/ado-5599-from-ai-button-alignment.spec.ts
new file mode 100644
index 00000000000..9cff0148469
--- /dev/null
+++ b/packages/quality/testing/playwright/tests/e2e/regression/ado-5599-from-ai-button-alignment.spec.ts
@@ -0,0 +1,51 @@
+import { test, expect } from '../../../fixtures/base';
+import type { Locator } from '@playwright/test';
+
+async function expectButtonAligned(inputBorder: Locator, fromAiButton: Locator) {
+	await expect(inputBorder).toBeVisible();
+	await expect(fromAiButton).toBeVisible();
+
+	const inputBounds = await inputBorder.boundingBox();
+	const buttonBounds = await fromAiButton.boundingBox();
+	expect(inputBounds).not.toBeNull();
+	expect(buttonBounds).not.toBeNull();
+
+	expect(buttonBounds).toMatchObject({
+		y: inputBounds!.y,
+		height: inputBounds!.height,
+	});
+}
+
+test.describe(
+	'ADO-5599: From AI button alignment',
+	{ annotation: [{ type: 'owner', description: 'Adore' }] },
+	() => {
+		test('aligns the From AI button outline with the tool parameter input border', async ({
+			n8n,
+		}) => {
+			await n8n.start.fromBlankCanvas();
+			await n8n.canvas.addNode('AI Agent', { closeNDV: true });
+			await n8n.canvas.getInputPlusEndpointByType('AI Agent', 'ai_tool').click();
+			await n8n.canvas.nodeCreator.searchFor('SearXNG');
+			await n8n.canvas.nodeCreator.selectItem('SearXNG');
+			await n8n.ndv.addParameterOptionByName('Language');
+
+			await expectButtonAligned(
+				n8n.ndv.getParameterInputBorder('language'),
+				n8n.ndv.getFromAiOverrideButton('language'),
+			);
+
+			await n8n.ndv.addParameterOptionByName('Number of Results');
+			await expectButtonAligned(
+				n8n.ndv.getParameterNumberBorder('numResults'),
+				n8n.ndv.getFromAiOverrideButton('numResults'),
+			);
+
+			await n8n.ndv.setParameterInput('language', '={{ $json.language }}');
+			await expectButtonAligned(
+				n8n.ndv.getParameterExpressionBorder('language'),
+				n8n.ndv.getFromAiOverrideButton('language'),
+			);
+		});
+	},
+);