diff --git a/packages/webhooks/source/listener.test.ts b/packages/webhooks/source/listener.test.ts
index 7aa5c7e46..abb3fba3e 100644
--- a/packages/webhooks/source/listener.test.ts
+++ b/packages/webhooks/source/listener.test.ts
@@ -146,6 +146,30 @@ describe<{
 		expectFinishedEventData(spyOnDispatchArguments[1]);
 	});
 
+	it("should broadcast satisfied webhook condition with nested key", async ({ database, listener }) => {
+		const spyOnPost = stub(Utils.http, "post").resolvedValue({
+			statusCode: 200,
+		});
+		const spyOnDispatch = stub(eventDispatcher, "dispatch");
+
+		webhook.conditions = [
+			{
+				condition: "eq",
+				key: "some.nested.prop",
+				value: 1,
+			},
+		];
+		database.create(webhook);
+
+		await listener.handle({ data: { some: { nested: { prop: 1 } } }, name: "event" });
+
+		spyOnPost.calledOnce();
+		spyOnDispatch.calledOnce();
+		const spyOnDispatchArguments = spyOnDispatch.getCallArgs(0);
+		assert.equal(spyOnDispatchArguments[0], WebhookEvent.Broadcasted);
+		expectFinishedEventData(spyOnDispatchArguments[1]);
+	});
+
 	it("should not broadcast if webhook condition is not satisfied", async ({ database, listener }) => {
 		const spyOnPost = stub(Utils.http, "post");
 
@@ -163,6 +187,23 @@ describe<{
 		spyOnPost.neverCalled();
 	});
 
+	it("should not broadcast if webhook condition with nested key is not satisfied", async ({ database, listener }) => {
+		const spyOnPost = stub(Utils.http, "post");
+
+		webhook.conditions = [
+			{
+				condition: "eq",
+				key: "some.nested.prop",
+				value: 1,
+			},
+		];
+		database.create(webhook);
+
+		await listener.handle({ data: { some: { nested: { prop: 2 } } }, name: "event" });
+
+		spyOnPost.neverCalled();
+	});
+
 	it("should not broadcast if webhook condition throws error", async ({ database, listener }) => {
 		const spyOnEq = stub(conditions, "eq").callsFake(() => {
 			throw new Error("dummy error");
diff --git a/packages/webhooks/source/listener.ts b/packages/webhooks/source/listener.ts
index ea4e24422..1b0bc1816 100644
--- a/packages/webhooks/source/listener.ts
+++ b/packages/webhooks/source/listener.ts
@@ -1,6 +1,7 @@
 import { inject, injectable } from "@mainsail/container";
 import { Contracts, Identifiers } from "@mainsail/contracts";
 import { Utils } from "@mainsail/kernel";
+import { get } from "@mainsail/utils";
 import { performance } from "perf_hooks";
 
 import { conditions } from "./conditions.js";
@@ -102,7 +103,7 @@ export class Listener {
 					try {
 						const satisfies = conditions[condition.condition];
 
-						if (satisfies(payload[condition.key], condition.value)) {
+						if (satisfies(get(payload, condition.key), condition.value)) {
 							return true;
 						}
 					} catch {