diff --git a/spring-web/src/main/java/org/springframework/web/server/session/InMemoryWebSessionStore.java b/spring-web/src/main/java/org/springframework/web/server/session/InMemoryWebSessionStore.java
index 6e76d76e9c1..e76b133363e 100644
--- a/spring-web/src/main/java/org/springframework/web/server/session/InMemoryWebSessionStore.java
+++ b/spring-web/src/main/java/org/springframework/web/server/session/InMemoryWebSessionStore.java
@@ -280,7 +280,7 @@ public class InMemoryWebSessionStore implements WebSessionStore {
 		private void checkMaxSessionsLimit() {
 			if (sessions.size() >= maxSessions) {
 				expiredSessionChecker.removeExpiredSessions(clock.instant());
-				if (sessions.size() >= maxSessions) {
+				if (sessions.size() >= maxSessions && !sessions.containsKey(this.getId())) {
 					throw new IllegalStateException("Max sessions limit reached: " + sessions.size());
 				}
 			}
diff --git a/spring-web/src/test/java/org/springframework/web/server/session/InMemoryWebSessionStoreTests.java b/spring-web/src/test/java/org/springframework/web/server/session/InMemoryWebSessionStoreTests.java
index 7847cc3537c..baeac73d008 100644
--- a/spring-web/src/test/java/org/springframework/web/server/session/InMemoryWebSessionStoreTests.java
+++ b/spring-web/src/test/java/org/springframework/web/server/session/InMemoryWebSessionStoreTests.java
@@ -23,6 +23,7 @@ import java.util.stream.IntStream;
 
 import org.junit.jupiter.api.Test;
 import reactor.core.scheduler.Schedulers;
+import reactor.test.StepVerifier;
 
 import org.springframework.beans.DirectFieldAccessor;
 import org.springframework.web.server.WebSession;
@@ -157,6 +158,25 @@ class InMemoryWebSessionStoreTests {
 				.withMessage("Max sessions limit reached: 10");
 	}
 
+	@Test
+	void updateSession() {
+		WebSession oneWebSession = insertSession();
+
+		StepVerifier.create(oneWebSession.save())
+				.expectComplete()
+				.verify();
+	}
+
+	@Test
+	void updateSession_whenMaxSessionsReached() {
+		WebSession onceWebSession = insertSession();
+		IntStream.range(1, 10000).forEach(i -> insertSession());
+
+		StepVerifier.create(onceWebSession.save())
+				.expectComplete()
+				.verify();
+	}
+
 
 	private WebSession insertSession() {
 		WebSession session = this.store.createWebSession().block();