diff --git a/CHANGELOG.md b/CHANGELOG.md
index 54d8e895bb..3d17169c16 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -10,6 +10,8 @@
 ### Features
 
 - Add current activity name to app context ([#2999](https://github.com/getsentry/sentry-java/pull/2999))
+- Add `MonitorConfig` param to `CheckInUtils.withCheckIn` ([#3038](https://github.com/getsentry/sentry-java/pull/3038))
+  - This makes it easier to automatically create or update (upsert) monitors.
 
 ## 6.33.1
 
diff --git a/sentry/api/sentry.api b/sentry/api/sentry.api
index 4272f044b4..d82c53853b 100644
--- a/sentry/api/sentry.api
+++ b/sentry/api/sentry.api
@@ -4325,6 +4325,7 @@ public abstract class io/sentry/transport/TransportResult {
 public final class io/sentry/util/CheckInUtils {
 	public fun <init> ()V
 	public static fun isIgnored (Ljava/util/List;Ljava/lang/String;)Z
+	public static fun withCheckIn (Ljava/lang/String;Lio/sentry/MonitorConfig;Ljava/util/concurrent/Callable;)Ljava/lang/Object;
 	public static fun withCheckIn (Ljava/lang/String;Ljava/util/concurrent/Callable;)Ljava/lang/Object;
 }
 
diff --git a/sentry/src/main/java/io/sentry/util/CheckInUtils.java b/sentry/src/main/java/io/sentry/util/CheckInUtils.java
index 9d4446226e..e15603adaf 100644
--- a/sentry/src/main/java/io/sentry/util/CheckInUtils.java
+++ b/sentry/src/main/java/io/sentry/util/CheckInUtils.java
@@ -4,6 +4,7 @@
 import io.sentry.CheckInStatus;
 import io.sentry.DateUtils;
 import io.sentry.IHub;
+import io.sentry.MonitorConfig;
 import io.sentry.Sentry;
 import io.sentry.protocol.SentryId;
 import java.util.List;
@@ -18,12 +19,17 @@ public final class CheckInUtils {
   /**
    * Helper method to send monitor check-ins for a {@link Callable}
    *
+   * @param monitorSlug - the slug of the monitor
+   * @param monitorConfig - configuration of the monitor, can be used for upserting schedule
    * @param callable - the {@link Callable} to be called
    * @return the return value of the {@link Callable}
    * @param <U> - the result type of the {@link Callable}
    */
   public static <U> U withCheckIn(
-      final @NotNull String monitorSlug, final @NotNull Callable<U> callable) throws Exception {
+      final @NotNull String monitorSlug,
+      final @Nullable MonitorConfig monitorConfig,
+      final @NotNull Callable<U> callable)
+      throws Exception {
     final @NotNull IHub hub = Sentry.getCurrentHub();
     final long startTime = System.currentTimeMillis();
     boolean didError = false;
@@ -31,8 +37,11 @@ public static <U> U withCheckIn(
     hub.pushScope();
     TracingUtils.startNewTrace(hub);
 
-    @Nullable
-    SentryId checkInId = hub.captureCheckIn(new CheckIn(monitorSlug, CheckInStatus.IN_PROGRESS));
+    CheckIn inProgressCheckIn = new CheckIn(monitorSlug, CheckInStatus.IN_PROGRESS);
+    if (monitorConfig != null) {
+      inProgressCheckIn.setMonitorConfig(monitorConfig);
+    }
+    @Nullable SentryId checkInId = hub.captureCheckIn(inProgressCheckIn);
     try {
       return callable.call();
     } catch (Throwable t) {
@@ -47,6 +56,19 @@ public static <U> U withCheckIn(
     }
   }
 
+  /**
+   * Helper method to send monitor check-ins for a {@link Callable}
+   *
+   * @param monitorSlug - the slug of the monitor
+   * @param callable - the {@link Callable} to be called
+   * @return the return value of the {@link Callable}
+   * @param <U> - the result type of the {@link Callable}
+   */
+  public static <U> U withCheckIn(
+      final @NotNull String monitorSlug, final @NotNull Callable<U> callable) throws Exception {
+    return withCheckIn(monitorSlug, null, callable);
+  }
+
   /** Checks if a check-in for a monitor (CRON) has been ignored. */
   @ApiStatus.Internal
   public static boolean isIgnored(
diff --git a/sentry/src/test/java/io/sentry/util/CheckInUtilsTest.kt b/sentry/src/test/java/io/sentry/util/CheckInUtilsTest.kt
index ccff57821a..fdc9b0151e 100644
--- a/sentry/src/test/java/io/sentry/util/CheckInUtilsTest.kt
+++ b/sentry/src/test/java/io/sentry/util/CheckInUtilsTest.kt
@@ -2,6 +2,9 @@ package io.sentry.util
 
 import io.sentry.CheckInStatus
 import io.sentry.IHub
+import io.sentry.MonitorConfig
+import io.sentry.MonitorSchedule
+import io.sentry.MonitorScheduleUnit
 import io.sentry.Sentry
 import org.mockito.Mockito
 import org.mockito.kotlin.any
@@ -13,6 +16,7 @@ import java.lang.RuntimeException
 import kotlin.test.Test
 import kotlin.test.assertEquals
 import kotlin.test.assertFalse
+import kotlin.test.assertSame
 import kotlin.test.assertTrue
 
 class CheckInUtilsTest {
@@ -111,4 +115,36 @@ class CheckInUtilsTest {
             }
         }
     }
+
+    @Test
+    fun `sends check-in for wrapped supplier with upsert`() {
+        Mockito.mockStatic(Sentry::class.java).use { sentry ->
+            val hub = mock<IHub>()
+            sentry.`when`<Any> { Sentry.getCurrentHub() }.thenReturn(hub)
+            val monitorConfig = MonitorConfig(MonitorSchedule.interval(7, MonitorScheduleUnit.DAY))
+            val returnValue = CheckInUtils.withCheckIn("monitor-1", monitorConfig) {
+                "test1"
+            }
+
+            assertEquals("test1", returnValue)
+            inOrder(hub) {
+                verify(hub).pushScope()
+                verify(hub).configureScope(any())
+                verify(hub).captureCheckIn(
+                    check {
+                        assertEquals("monitor-1", it.monitorSlug)
+                        assertSame(monitorConfig, it.monitorConfig)
+                        assertEquals(CheckInStatus.IN_PROGRESS.apiName(), it.status)
+                    }
+                )
+                verify(hub).captureCheckIn(
+                    check {
+                        assertEquals("monitor-1", it.monitorSlug)
+                        assertEquals(CheckInStatus.OK.apiName(), it.status)
+                    }
+                )
+                verify(hub).popScope()
+            }
+        }
+    }
 }