diff --git a/driver-core/src/main/com/mongodb/internal/async/function/RetryState.java b/driver-core/src/main/com/mongodb/internal/async/function/RetryState.java
index 3afb97c512a..3f8707a237f 100644
--- a/driver-core/src/main/com/mongodb/internal/async/function/RetryState.java
+++ b/driver-core/src/main/com/mongodb/internal/async/function/RetryState.java
@@ -186,16 +186,20 @@ private void doAdvanceOrThrow(final Throwable attemptException,
             final boolean onlyRuntimeExceptions) throws Throwable {
         assertTrue(attempt() < attempts);
         assertNotNull(attemptException);
-        if (attemptException instanceof MongoOperationTimeoutException) {
-            throw attemptException;
-        }
         if (onlyRuntimeExceptions) {
             assertTrue(isRuntime(attemptException));
         }
         assertTrue(!isFirstAttempt() || previouslyChosenException == null);
         Throwable newlyChosenException = transformException(previouslyChosenException, attemptException, onlyRuntimeExceptions, exceptionTransformer);
 
-        if (isLastAttempt()) {
+        /*
+         * A MongoOperationTimeoutException indicates that the operation timed out, either during command execution or server selection.
+         * The timeout for server selection is determined by the computedServerSelectionMS = min(serverSelectionTimeoutMS, timeoutMS).
+         *
+         * The isLastAttempt() method checks if the timeoutMS has expired, which could be greater than the computedServerSelectionMS.
+         * Therefore, it's important to check if the exception is an instance of MongoOperationTimeoutException to detect a timeout.
+         */
+        if (isLastAttempt() || attemptException instanceof MongoOperationTimeoutException) {
             previouslyChosenException = newlyChosenException;
             /*
              * The function of isLastIteration() is to indicate if retrying has been explicitly halted. Such a stop is not interpreted as
diff --git a/driver-core/src/test/unit/com/mongodb/internal/async/function/RetryStateTest.java b/driver-core/src/test/unit/com/mongodb/internal/async/function/RetryStateTest.java
index 1d1a76797de..ecc8dda3592 100644
--- a/driver-core/src/test/unit/com/mongodb/internal/async/function/RetryStateTest.java
+++ b/driver-core/src/test/unit/com/mongodb/internal/async/function/RetryStateTest.java
@@ -22,6 +22,7 @@
 import com.mongodb.internal.async.function.LoopState.AttachmentKey;
 import com.mongodb.internal.operation.retry.AttachmentKeys;
 import org.junit.jupiter.api.Assertions;
+import org.junit.jupiter.api.DisplayName;
 import org.junit.jupiter.api.Test;
 import org.junit.jupiter.params.ParameterizedTest;
 import org.junit.jupiter.params.provider.Arguments;
@@ -268,6 +269,68 @@ void advanceOrThrowPredicateFalse(final TimeoutContext timeoutContext) {
         assertThrows(attemptException.getClass(), () -> retryState.advanceOrThrow(attemptException, (e1, e2) -> e2, (rs, e) -> false));
     }
 
+    @ParameterizedTest
+    @MethodSource({"infiniteTimeout"})
+    @DisplayName("should rethrow detected timeout exception even if timeout in retry state is not expired")
+    void advanceReThrowDetectedTimeoutExceptionEvenIfTimeoutInRetryStateIsNotExpired(final TimeoutContext timeoutContext) {
+        RetryState retryState = new RetryState(timeoutContext);
+
+        MongoOperationTimeoutException expectedTimeoutException = TimeoutContext.createMongoTimeoutException("Server selection failed");
+        MongoOperationTimeoutException actualTimeoutException =
+                assertThrows(expectedTimeoutException.getClass(), () -> retryState.advanceOrThrow(expectedTimeoutException,
+                        (e1, e2) -> expectedTimeoutException,
+                        (rs, e) -> false));
+
+        Assertions.assertEquals(actualTimeoutException, expectedTimeoutException);
+    }
+
+    @Test
+    @DisplayName("should throw timeout exception from retry, when transformer swallows original timeout exception")
+    void advanceThrowTimeoutExceptionWhenTransformerSwallowOriginalTimeoutException() {
+        RetryState retryState = new RetryState(TIMEOUT_CONTEXT_INFINITE_GLOBAL_TIMEOUT);
+        RuntimeException previousAttemptException = new RuntimeException() {
+        };
+        MongoOperationTimeoutException expectedTimeoutException = TimeoutContext.createMongoTimeoutException("Server selection failed");
+
+        retryState.advanceOrThrow(previousAttemptException,
+                (e1, e2) -> previousAttemptException,
+                (rs, e) -> true);
+
+        MongoOperationTimeoutException actualTimeoutException =
+                assertThrows(expectedTimeoutException.getClass(), () -> retryState.advanceOrThrow(expectedTimeoutException,
+                        (e1, e2) -> previousAttemptException,
+                        (rs, e) -> false));
+
+        Assertions.assertNotEquals(actualTimeoutException, expectedTimeoutException);
+        Assertions.assertEquals("Retry attempt timed out.", actualTimeoutException.getMessage());
+        Assertions.assertEquals(previousAttemptException, actualTimeoutException.getCause(),
+                "Retry timeout exception should have a cause if transformer returned non-timeout exception.");
+    }
+
+
+    @Test
+    @DisplayName("should throw original timeout exception from retry, when transformer returns original timeout exception")
+    void advanceThrowOriginalTimeoutExceptionWhenTransformerReturnsOriginalTimeoutException() {
+        RetryState retryState = new RetryState(TIMEOUT_CONTEXT_INFINITE_GLOBAL_TIMEOUT);
+        RuntimeException previousAttemptException = new RuntimeException() {
+        };
+        MongoOperationTimeoutException expectedTimeoutException = TimeoutContext
+                .createMongoTimeoutException("Server selection failed");
+
+        retryState.advanceOrThrow(previousAttemptException,
+                (e1, e2) -> previousAttemptException,
+                (rs, e) -> true);
+
+        MongoOperationTimeoutException actualTimeoutException =
+                assertThrows(expectedTimeoutException.getClass(), () -> retryState.advanceOrThrow(expectedTimeoutException,
+                        (e1, e2) -> expectedTimeoutException,
+                        (rs, e) -> false));
+
+        Assertions.assertEquals(actualTimeoutException, expectedTimeoutException);
+        Assertions.assertNull(actualTimeoutException.getCause(),
+                "Original timeout exception should not have a cause if transformer already returned timeout exception.");
+    }
+
     @Test
     void advanceOrThrowPredicateTrueAndLastAttempt() {
         RetryState retryState = RetryState.withNonRetryableState();