diff --git a/CHANGELOG.md b/CHANGELOG.md
index 4126d1706dd..10f53cef310 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -4,6 +4,7 @@
 
 ### Features
 
+- Send a monitor config derived from Spring `@Scheduled` with `@SentryCheckIn` check-ins by default, so Sentry creates or updates the monitor from code. Set `@SentryCheckIn(upsertMonitorConfig = false)` to turn this off ([#6215](https://github.com/getsentry/sentry-java/pull/6215))
 - Report the cellular network technology generation in `device.connection_effective_type`, for example `4g` or `5g` ([#6146](https://github.com/getsentry/sentry-java/pull/6146))
 
 ## 8.59.0
diff --git a/sentry-spring-7/api/sentry-spring-7.api b/sentry-spring-7/api/sentry-spring-7.api
index c9250b550fd..c5aaf0a5d1b 100644
--- a/sentry-spring-7/api/sentry-spring-7.api
+++ b/sentry-spring-7/api/sentry-spring-7.api
@@ -136,6 +136,7 @@ public final class io/sentry/spring7/cache/SentryCacheWrapper : org/springframew
 public abstract interface annotation class io/sentry/spring7/checkin/SentryCheckIn : java/lang/annotation/Annotation {
 	public abstract fun heartbeat ()Z
 	public abstract fun monitorSlug ()Ljava/lang/String;
+	public abstract fun upsertMonitorConfig ()Z
 	public abstract fun value ()Ljava/lang/String;
 }
 
diff --git a/sentry-spring-7/src/main/java/io/sentry/spring7/checkin/SentryCheckIn.java b/sentry-spring-7/src/main/java/io/sentry/spring7/checkin/SentryCheckIn.java
index 47cd80ab5b2..38491436786 100644
--- a/sentry-spring-7/src/main/java/io/sentry/spring7/checkin/SentryCheckIn.java
+++ b/sentry-spring-7/src/main/java/io/sentry/spring7/checkin/SentryCheckIn.java
@@ -29,6 +29,17 @@
    */
   boolean heartbeat() default false;
 
+  /**
+   * Whether to send the schedule and zone from the method's {@code @Scheduled} with check-ins, so
+   * Sentry creates or updates the monitor. On by default. Set to false to manage the monitor's
+   * schedule in Sentry instead.
+   *
+   * <p>Heartbeat check-ins never send a monitor config.
+   *
+   * @return true to send a monitor config, true by default
+   */
+  boolean upsertMonitorConfig() default true;
+
   /**
    * Monitor slug. If not set, no check-in will be sent.
    *
diff --git a/sentry-spring-7/src/main/java/io/sentry/spring7/checkin/SentryCheckInAdvice.java b/sentry-spring-7/src/main/java/io/sentry/spring7/checkin/SentryCheckInAdvice.java
index e58e0e9dd97..3051acbb607 100644
--- a/sentry-spring-7/src/main/java/io/sentry/spring7/checkin/SentryCheckInAdvice.java
+++ b/sentry-spring-7/src/main/java/io/sentry/spring7/checkin/SentryCheckInAdvice.java
@@ -6,13 +6,21 @@
 import io.sentry.DateUtils;
 import io.sentry.IScopes;
 import io.sentry.ISentryLifecycleToken;
+import io.sentry.MonitorConfig;
 import io.sentry.ScopesAdapter;
 import io.sentry.SentryLevel;
 import io.sentry.protocol.SentryId;
 import io.sentry.time.Stopwatch;
+import io.sentry.util.MonitorConfigUtils;
 import io.sentry.util.Objects;
 import io.sentry.util.TracingUtils;
 import java.lang.reflect.Method;
+import java.time.Duration;
+import java.time.format.DateTimeParseException;
+import java.util.Map;
+import java.util.Set;
+import java.util.concurrent.ConcurrentHashMap;
+import java.util.concurrent.TimeUnit;
 import org.aopalliance.intercept.MethodInterceptor;
 import org.aopalliance.intercept.MethodInvocation;
 import org.jetbrains.annotations.ApiStatus;
@@ -20,7 +28,10 @@
 import org.jetbrains.annotations.Nullable;
 import org.springframework.aop.support.AopUtils;
 import org.springframework.context.EmbeddedValueResolverAware;
+import org.springframework.core.annotation.AnnotatedElementUtils;
 import org.springframework.core.annotation.AnnotationUtils;
+import org.springframework.scheduling.annotation.Scheduled;
+import org.springframework.util.ClassUtils;
 import org.springframework.util.ObjectUtils;
 import org.springframework.util.StringValueResolver;
 
@@ -31,10 +42,19 @@
 @ApiStatus.Internal
 @Open
 public class SentryCheckInAdvice implements MethodInterceptor, EmbeddedValueResolverAware {
+  // Spring before 5.3 parses crons with CronSequenceGenerator
+  private static final boolean LEGACY_CRON_PARSER =
+      !ClassUtils.isPresent(
+          "org.springframework.scheduling.support.CronExpression",
+          SentryCheckInAdvice.class.getClassLoader());
+
   private final @NotNull IScopes scopes;
 
   private @Nullable StringValueResolver resolver;
 
+  private final @NotNull Map<Method, CachedMonitorConfig> monitorConfigs =
+      new ConcurrentHashMap<>();
+
   public SentryCheckInAdvice() {
     this(ScopesAdapter.getInstance());
   }
@@ -87,6 +107,11 @@ public Object invoke(final @NotNull MethodInvocation invocation) throws Throwabl
       return invocation.proceed();
     }
 
+    final @Nullable MonitorConfig monitorConfig =
+        !isHeartbeatOnly && checkInAnnotation.upsertMonitorConfig()
+            ? monitorConfig(mostSpecificMethod)
+            : null;
+
     try (final @NotNull ISentryLifecycleToken ignored =
             scopes.forkedScopes("SentryCheckInAdvice").makeCurrent()) {
       TracingUtils.startNewTrace(scopes);
@@ -98,7 +123,9 @@ public Object invoke(final @NotNull MethodInvocation invocation) throws Throwabl
 
       try {
         if (!isHeartbeatOnly) {
-          checkInId = scopes.captureCheckIn(new CheckIn(monitorSlug, CheckInStatus.IN_PROGRESS));
+          final @NotNull CheckIn inProgress = new CheckIn(monitorSlug, CheckInStatus.IN_PROGRESS);
+          inProgress.setMonitorConfig(monitorConfig);
+          checkInId = scopes.captureCheckIn(inProgress);
         }
         return invocation.proceed();
       } catch (Throwable e) {
@@ -113,6 +140,96 @@ public Object invoke(final @NotNull MethodInvocation invocation) throws Throwabl
     }
   }
 
+  private @Nullable MonitorConfig monitorConfig(final @NotNull Method method) {
+    return monitorConfigs.computeIfAbsent(
+            method, key -> new CachedMonitorConfig(monitorConfigFromScheduled(key)))
+        .config;
+  }
+
+  private @Nullable MonitorConfig monitorConfigFromScheduled(final @NotNull Method method) {
+    try {
+      final @NotNull Set<Scheduled> schedules =
+          AnnotatedElementUtils.findMergedRepeatableAnnotations(method, Scheduled.class);
+      if (schedules.size() != 1) {
+        return null;
+      }
+      final @NotNull Scheduled scheduled = schedules.iterator().next();
+      // timeUnit only exists from Spring 5.3.10, so read it as an attribute
+      final @Nullable Object timeUnitAttribute =
+          AnnotationUtils.getAnnotationAttributes(scheduled).get("timeUnit");
+      final @NotNull TimeUnit timeUnit =
+          timeUnitAttribute instanceof TimeUnit
+              ? (TimeUnit) timeUnitAttribute
+              : TimeUnit.MILLISECONDS;
+      final @Nullable String cron = resolve(scheduled.cron());
+      // Spring only reads the zone for a cron
+      final @Nullable String zone =
+          cron == null || cron.isEmpty() ? null : resolve(scheduled.zone());
+      return MonitorConfigUtils.fromSpringScheduled(
+          cron,
+          zone,
+          periodMillis(scheduled.fixedRate(), scheduled.fixedRateString(), timeUnit),
+          periodMillis(scheduled.fixedDelay(), scheduled.fixedDelayString(), timeUnit),
+          LEGACY_CRON_PARSER);
+    } catch (RuntimeException e) {
+      scopes
+          .getOptions()
+          .getLogger()
+          .log(
+              SentryLevel.WARNING,
+              "Could not derive a monitor config from @Scheduled for method annotated with @SentryCheckIn.",
+              e);
+      return null;
+    }
+  }
+
+  private @Nullable Long periodMillis(
+      final long value, final @NotNull String valueString, final @NotNull TimeUnit timeUnit) {
+    if (value >= 0) {
+      return timeUnit.toMillis(value);
+    }
+    final @Nullable String resolved = resolve(valueString);
+    if (resolved == null || resolved.isEmpty()) {
+      return null;
+    }
+    final @NotNull String trimmed = resolved.trim();
+    @Nullable Long millis = null;
+    if (trimmed.startsWith("P") || trimmed.startsWith("p")) {
+      try {
+        millis = Duration.parse(trimmed).toMillis();
+      } catch (DateTimeParseException | ArithmeticException e) {
+        // logged below
+      }
+    } else {
+      millis = MonitorConfigUtils.parsePeriodMillis(trimmed, timeUnit);
+    }
+    if (millis == null) {
+      scopes
+          .getOptions()
+          .getLogger()
+          .log(
+              SentryLevel.DEBUG,
+              "Not sending a monitor config for @SentryCheckIn because the @Scheduled period '%s' could not be parsed.",
+              trimmed);
+    }
+    return millis;
+  }
+
+  private @Nullable String resolve(final @NotNull String value) {
+    if (resolver == null || value.isEmpty()) {
+      return value;
+    }
+    return resolver.resolveStringValue(value);
+  }
+
+  private static final class CachedMonitorConfig {
+    private final @Nullable MonitorConfig config;
+
+    private CachedMonitorConfig(final @Nullable MonitorConfig config) {
+      this.config = config;
+    }
+  }
+
   @Override
   public void setEmbeddedValueResolver(StringValueResolver resolver) {
     this.resolver = resolver;
diff --git a/sentry-spring-7/src/test/kotlin/io/sentry/spring7/SentryCheckInAdviceTest.kt b/sentry-spring-7/src/test/kotlin/io/sentry/spring7/SentryCheckInAdviceTest.kt
index e15affdbdd5..a071ba293ca 100644
--- a/sentry-spring-7/src/test/kotlin/io/sentry/spring7/SentryCheckInAdviceTest.kt
+++ b/sentry-spring-7/src/test/kotlin/io/sentry/spring7/SentryCheckInAdviceTest.kt
@@ -4,16 +4,21 @@ import io.sentry.CheckIn
 import io.sentry.CheckInStatus
 import io.sentry.IScopes
 import io.sentry.ISentryLifecycleToken
+import io.sentry.MonitorConfig
 import io.sentry.Sentry
 import io.sentry.SentryOptions
 import io.sentry.protocol.SentryId
 import io.sentry.spring7.checkin.SentryCheckIn
 import io.sentry.spring7.checkin.SentryCheckInAdviceConfiguration
 import io.sentry.spring7.checkin.SentryCheckInPointcutConfiguration
+import java.util.TimeZone
+import java.util.concurrent.TimeUnit
 import kotlin.test.BeforeTest
 import kotlin.test.Test
 import kotlin.test.assertEquals
 import kotlin.test.assertNotNull
+import kotlin.test.assertNull
+import kotlin.test.assertSame
 import org.junit.jupiter.api.assertThrows
 import org.junit.runner.RunWith
 import org.mockito.kotlin.any
@@ -32,6 +37,8 @@ import org.springframework.context.annotation.Configuration
 import org.springframework.context.annotation.EnableAspectJAutoProxy
 import org.springframework.context.annotation.Import
 import org.springframework.context.support.PropertySourcesPlaceholderConfigurer
+import org.springframework.scheduling.annotation.Scheduled
+import org.springframework.scheduling.annotation.Schedules
 import org.springframework.test.context.TestPropertySource
 import org.springframework.test.context.junit.jupiter.SpringJUnitConfig
 import org.springframework.test.context.junit4.SpringRunner
@@ -39,7 +46,15 @@ import org.springframework.util.StringValueResolver
 
 @RunWith(SpringRunner::class)
 @SpringJUnitConfig(SentryCheckInAdviceTest.Config::class)
-@TestPropertySource(properties = ["my.cron.slug = mypropertycronslug"])
+@TestPropertySource(
+  properties =
+    [
+      "my.cron.slug = mypropertycronslug",
+      "my.cron.schedule = 0 30 2 * * *",
+      "my.cron.zone = America/New_York",
+      "my.cron.empty.zone = ",
+    ]
+)
 class SentryCheckInAdviceTest {
 
   @Autowired lateinit var sampleService: SampleService
@@ -50,6 +65,8 @@ class SentryCheckInAdviceTest {
 
   @Autowired lateinit var sampleServiceSpringProperties: SampleServiceSpringProperties
 
+  @Autowired lateinit var sampleServiceScheduled: SampleServiceScheduled
+
   @Autowired lateinit var scopes: IScopes
 
   val lifecycleToken = mock<ISentryLifecycleToken>()
@@ -74,6 +91,7 @@ class SentryCheckInAdviceTest {
     val inProgressCheckIn = checkInCaptor.firstValue
     assertEquals("monitor_slug_1", inProgressCheckIn.monitorSlug)
     assertEquals(CheckInStatus.IN_PROGRESS.apiName(), inProgressCheckIn.status)
+    assertNull(inProgressCheckIn.monitorConfig)
 
     val doneCheckIn = checkInCaptor.lastValue
     assertEquals("monitor_slug_1", doneCheckIn.monitorSlug)
@@ -228,6 +246,150 @@ class SentryCheckInAdviceTest {
     order.verify(lifecycleToken).close()
   }
 
+  @Test
+  fun `cron with zone is sent as crontab monitor config`() {
+    val config = inProgressMonitorConfig { sampleServiceScheduled.cronWithZone() }
+    assertNotNull(config)
+    assertEquals("crontab", config.schedule.type)
+    assertEquals("15 10 * * 1-5", config.schedule.value)
+    assertNull(config.schedule.unit)
+    assertEquals("Europe/Vienna", config.timezone)
+  }
+
+  @Test
+  fun `cron without zone is sent in the JVM default zone`() {
+    val defaultTimeZone = TimeZone.getDefault()
+    TimeZone.setDefault(TimeZone.getTimeZone("Asia/Tokyo"))
+    try {
+      val config = inProgressMonitorConfig { sampleServiceScheduled.cron() }
+      assertEquals("0 2 * * *", config?.schedule?.value)
+      assertEquals("Asia/Tokyo", config?.timezone)
+    } finally {
+      TimeZone.setDefault(defaultTimeZone)
+    }
+  }
+
+  @Test
+  fun `cron and zone placeholders are resolved`() {
+    val config = inProgressMonitorConfig { sampleServiceScheduled.cronFromProperties() }
+    assertEquals("30 2 * * *", config?.schedule?.value)
+    assertEquals("America/New_York", config?.timezone)
+  }
+
+  @Test
+  fun `fixed rate with time unit is sent as interval monitor config`() {
+    val config = inProgressMonitorConfig { sampleServiceScheduled.fixedRateHours() }
+    assertNotNull(config)
+    assertEquals("interval", config.schedule.type)
+    assertEquals("2", config.schedule.value)
+    assertEquals("hour", config.schedule.unit)
+  }
+
+  @Test
+  fun `ISO-8601 fixed rate string is sent as interval monitor config`() {
+    val config = inProgressMonitorConfig { sampleServiceScheduled.fixedRateIso() }
+    assertEquals("10", config?.schedule?.value)
+    assertEquals("minute", config?.schedule?.unit)
+  }
+
+  @Test
+  fun `simple duration fixed rate string is sent as interval monitor config`() {
+    val config = inProgressMonitorConfig { sampleServiceScheduled.fixedRateSimpleDuration() }
+    assertEquals("interval", config?.schedule?.type)
+    assertEquals("5", config?.schedule?.value)
+    assertEquals("minute", config?.schedule?.unit)
+  }
+
+  @Test
+  fun `fixed delay sends no monitor config`() {
+    assertNull(inProgressMonitorConfig { sampleServiceScheduled.fixedDelay() })
+    assertNull(inProgressMonitorConfig { sampleServiceScheduled.fixedDelayIso() })
+  }
+
+  @Test
+  fun `disabled cron sends no monitor config`() {
+    assertNull(inProgressMonitorConfig { sampleServiceScheduled.disabledCron() })
+  }
+
+  @Test
+  fun `zone placeholder resolving to empty uses the JVM default zone`() {
+    val defaultTimeZone = TimeZone.getDefault()
+    TimeZone.setDefault(TimeZone.getTimeZone("Asia/Tokyo"))
+    try {
+      val config = inProgressMonitorConfig { sampleServiceScheduled.cronWithEmptyZone() }
+      assertEquals("0 3 * * *", config?.schedule?.value)
+      assertEquals("Asia/Tokyo", config?.timezone)
+    } finally {
+      TimeZone.setDefault(defaultTimeZone)
+    }
+  }
+
+  @Test
+  fun `cron zone overrides the default timezone from options`() {
+    val options =
+      SentryOptions().apply {
+        cron = SentryOptions.Cron().apply { defaultTimezone = "Europe/Berlin" }
+      }
+    whenever(scopes.options).thenReturn(options)
+    val config = inProgressMonitorConfig { sampleServiceScheduled.cronWithZoneAndDefaults() }
+    assertEquals("Europe/Vienna", config?.timezone)
+  }
+
+  @Test
+  fun `unresolvable cron placeholder sends no monitor config`() {
+    assertNull(inProgressMonitorConfig { sampleServiceScheduled.unresolvableCron() })
+  }
+
+  @Test
+  fun `exception while deriving monitor config sends no monitor config and runs the job`() {
+    var result = 0
+    assertNull(inProgressMonitorConfig { result = sampleServiceScheduled.derivationThrows() })
+    assertEquals(1, result)
+  }
+
+  @Test
+  fun `monitor config is derived once per method`() {
+    val first = inProgressMonitorConfig { sampleServiceScheduled.fixedRateHours() }
+    val second = inProgressMonitorConfig { sampleServiceScheduled.fixedRateHours() }
+    assertNotNull(first)
+    assertSame(first, second)
+  }
+
+  @Test
+  fun `multiple schedules send no monitor config`() {
+    assertNull(inProgressMonitorConfig { sampleServiceScheduled.multipleSchedules() })
+  }
+
+  @Test
+  fun `schedules container sends no monitor config`() {
+    assertNull(inProgressMonitorConfig { sampleServiceScheduled.schedulesContainer() })
+  }
+
+  @Test
+  fun `upsertMonitorConfig false sends no monitor config`() {
+    assertNull(inProgressMonitorConfig { sampleServiceScheduled.upsertDisabled() })
+  }
+
+  @Test
+  fun `heartbeat with @Scheduled sends a single check-in without monitor config`() {
+    val checkInCaptor = argumentCaptor<CheckIn>()
+    whenever(scopes.captureCheckIn(checkInCaptor.capture())).thenReturn(SentryId())
+    sampleServiceScheduled.heartbeat()
+    assertEquals(1, checkInCaptor.allValues.size)
+    assertEquals(CheckInStatus.OK.apiName(), checkInCaptor.firstValue.status)
+    assertNull(checkInCaptor.firstValue.monitorConfig)
+  }
+
+  private fun inProgressMonitorConfig(block: () -> Unit): MonitorConfig? {
+    val checkInCaptor = argumentCaptor<CheckIn>()
+    whenever(scopes.captureCheckIn(checkInCaptor.capture())).thenReturn(SentryId())
+    block()
+    assertEquals(2, checkInCaptor.allValues.size)
+    assertEquals(CheckInStatus.IN_PROGRESS.apiName(), checkInCaptor.firstValue.status)
+    assertNull(checkInCaptor.lastValue.monitorConfig)
+    return checkInCaptor.firstValue.monitorConfig
+  }
+
   @Configuration
   @EnableAspectJAutoProxy(proxyTargetClass = true)
   @Import(SentryCheckInAdviceConfiguration::class, SentryCheckInPointcutConfiguration::class)
@@ -241,6 +403,8 @@ class SentryCheckInAdviceTest {
 
     @Bean open fun sampleServiceSpringProperties() = SampleServiceSpringProperties()
 
+    @Bean open fun sampleServiceScheduled() = SampleServiceScheduled()
+
     @Bean
     open fun scopes(): IScopes {
       val scopes = mock<IScopes>()
@@ -291,6 +455,72 @@ class SentryCheckInAdviceTest {
     open fun helloExceptionProperty() = 1
   }
 
+  open class SampleServiceScheduled {
+
+    @SentryCheckIn("cron_zone")
+    @Scheduled(cron = "0 15 10 * * MON-FRI", zone = "Europe/Vienna")
+    open fun cronWithZone() {}
+
+    @SentryCheckIn("cron") @Scheduled(cron = "0 0 2 * * *") open fun cron() {}
+
+    @SentryCheckIn("cron_properties")
+    @Scheduled(cron = "\${my.cron.schedule}", zone = "\${my.cron.zone}")
+    open fun cronFromProperties() {}
+
+    @SentryCheckIn("fixed_rate_hours")
+    @Scheduled(fixedRate = 2, timeUnit = TimeUnit.HOURS)
+    open fun fixedRateHours() {}
+
+    @SentryCheckIn("fixed_rate_iso")
+    @Scheduled(fixedRateString = "PT10M")
+    open fun fixedRateIso() {}
+
+    @SentryCheckIn("fixed_rate_simple")
+    @Scheduled(fixedRateString = "5m")
+    open fun fixedRateSimpleDuration() {}
+
+    @SentryCheckIn("fixed_delay") @Scheduled(fixedDelay = 300_000) open fun fixedDelay() {}
+
+    @SentryCheckIn("fixed_delay_iso")
+    @Scheduled(fixedDelayString = "PT10M")
+    open fun fixedDelayIso() {}
+
+    @SentryCheckIn("disabled_cron") @Scheduled(cron = "-") open fun disabledCron() {}
+
+    @SentryCheckIn("cron_empty_zone")
+    @Scheduled(cron = "0 0 3 * * *", zone = "\${my.cron.empty.zone}")
+    open fun cronWithEmptyZone() {}
+
+    @SentryCheckIn("cron_zone_defaults")
+    @Scheduled(cron = "0 0 4 * * *", zone = "Europe/Vienna")
+    open fun cronWithZoneAndDefaults() {}
+
+    @SentryCheckIn("schedules_container")
+    @Schedules(Scheduled(cron = "0 0 1 * * *"), Scheduled(cron = "0 0 13 * * *"))
+    open fun schedulesContainer() {}
+
+    @SentryCheckIn("unresolvable_cron")
+    @Scheduled(cron = "\${my.cron.missing}")
+    open fun unresolvableCron() {}
+
+    @SentryCheckIn("derivation_throws")
+    @Scheduled(cron = "\${my.cron.exception.property}")
+    open fun derivationThrows() = 1
+
+    @SentryCheckIn("multiple")
+    @Scheduled(cron = "0 0 1 * * *")
+    @Scheduled(cron = "0 0 13 * * *")
+    open fun multipleSchedules() {}
+
+    @SentryCheckIn("upsert_disabled", upsertMonitorConfig = false)
+    @Scheduled(cron = "0 0 1 * * *")
+    open fun upsertDisabled() {}
+
+    @SentryCheckIn("heartbeat", heartbeat = true)
+    @Scheduled(cron = "0 0 1 * * *")
+    open fun heartbeat() {}
+  }
+
   class MyPropertyPlaceholderConfigurer : PropertySourcesPlaceholderConfigurer() {
 
     override fun doProcessProperties(
diff --git a/sentry-spring-jakarta/api/sentry-spring-jakarta.api b/sentry-spring-jakarta/api/sentry-spring-jakarta.api
index 24b9af7e14b..aa1dae669ba 100644
--- a/sentry-spring-jakarta/api/sentry-spring-jakarta.api
+++ b/sentry-spring-jakarta/api/sentry-spring-jakarta.api
@@ -136,6 +136,7 @@ public final class io/sentry/spring/jakarta/cache/SentryCacheWrapper : org/sprin
 public abstract interface annotation class io/sentry/spring/jakarta/checkin/SentryCheckIn : java/lang/annotation/Annotation {
 	public abstract fun heartbeat ()Z
 	public abstract fun monitorSlug ()Ljava/lang/String;
+	public abstract fun upsertMonitorConfig ()Z
 	public abstract fun value ()Ljava/lang/String;
 }
 
diff --git a/sentry-spring-jakarta/src/main/java/io/sentry/spring/jakarta/checkin/SentryCheckIn.java b/sentry-spring-jakarta/src/main/java/io/sentry/spring/jakarta/checkin/SentryCheckIn.java
index bfb6b724b8f..5e180daa0e6 100644
--- a/sentry-spring-jakarta/src/main/java/io/sentry/spring/jakarta/checkin/SentryCheckIn.java
+++ b/sentry-spring-jakarta/src/main/java/io/sentry/spring/jakarta/checkin/SentryCheckIn.java
@@ -29,6 +29,17 @@
    */
   boolean heartbeat() default false;
 
+  /**
+   * Whether to send the schedule and zone from the method's {@code @Scheduled} with check-ins, so
+   * Sentry creates or updates the monitor. On by default. Set to false to manage the monitor's
+   * schedule in Sentry instead.
+   *
+   * <p>Heartbeat check-ins never send a monitor config.
+   *
+   * @return true to send a monitor config, true by default
+   */
+  boolean upsertMonitorConfig() default true;
+
   /**
    * Monitor slug. If not set, no check-in will be sent.
    *
diff --git a/sentry-spring-jakarta/src/main/java/io/sentry/spring/jakarta/checkin/SentryCheckInAdvice.java b/sentry-spring-jakarta/src/main/java/io/sentry/spring/jakarta/checkin/SentryCheckInAdvice.java
index 1e3697e781d..1260e9ba05a 100644
--- a/sentry-spring-jakarta/src/main/java/io/sentry/spring/jakarta/checkin/SentryCheckInAdvice.java
+++ b/sentry-spring-jakarta/src/main/java/io/sentry/spring/jakarta/checkin/SentryCheckInAdvice.java
@@ -6,13 +6,21 @@
 import io.sentry.DateUtils;
 import io.sentry.IScopes;
 import io.sentry.ISentryLifecycleToken;
+import io.sentry.MonitorConfig;
 import io.sentry.ScopesAdapter;
 import io.sentry.SentryLevel;
 import io.sentry.protocol.SentryId;
 import io.sentry.time.Stopwatch;
+import io.sentry.util.MonitorConfigUtils;
 import io.sentry.util.Objects;
 import io.sentry.util.TracingUtils;
 import java.lang.reflect.Method;
+import java.time.Duration;
+import java.time.format.DateTimeParseException;
+import java.util.Map;
+import java.util.Set;
+import java.util.concurrent.ConcurrentHashMap;
+import java.util.concurrent.TimeUnit;
 import org.aopalliance.intercept.MethodInterceptor;
 import org.aopalliance.intercept.MethodInvocation;
 import org.jetbrains.annotations.ApiStatus;
@@ -20,7 +28,10 @@
 import org.jetbrains.annotations.Nullable;
 import org.springframework.aop.support.AopUtils;
 import org.springframework.context.EmbeddedValueResolverAware;
+import org.springframework.core.annotation.AnnotatedElementUtils;
 import org.springframework.core.annotation.AnnotationUtils;
+import org.springframework.scheduling.annotation.Scheduled;
+import org.springframework.util.ClassUtils;
 import org.springframework.util.ObjectUtils;
 import org.springframework.util.StringValueResolver;
 
@@ -31,10 +42,19 @@
 @ApiStatus.Internal
 @Open
 public class SentryCheckInAdvice implements MethodInterceptor, EmbeddedValueResolverAware {
+  // Spring before 5.3 parses crons with CronSequenceGenerator
+  private static final boolean LEGACY_CRON_PARSER =
+      !ClassUtils.isPresent(
+          "org.springframework.scheduling.support.CronExpression",
+          SentryCheckInAdvice.class.getClassLoader());
+
   private final @NotNull IScopes scopes;
 
   private @Nullable StringValueResolver resolver;
 
+  private final @NotNull Map<Method, CachedMonitorConfig> monitorConfigs =
+      new ConcurrentHashMap<>();
+
   public SentryCheckInAdvice() {
     this(ScopesAdapter.getInstance());
   }
@@ -87,6 +107,11 @@ public Object invoke(final @NotNull MethodInvocation invocation) throws Throwabl
       return invocation.proceed();
     }
 
+    final @Nullable MonitorConfig monitorConfig =
+        !isHeartbeatOnly && checkInAnnotation.upsertMonitorConfig()
+            ? monitorConfig(mostSpecificMethod)
+            : null;
+
     try (final @NotNull ISentryLifecycleToken ignored =
             scopes.forkedScopes("SentryCheckInAdvice").makeCurrent()) {
       TracingUtils.startNewTrace(scopes);
@@ -98,7 +123,9 @@ public Object invoke(final @NotNull MethodInvocation invocation) throws Throwabl
 
       try {
         if (!isHeartbeatOnly) {
-          checkInId = scopes.captureCheckIn(new CheckIn(monitorSlug, CheckInStatus.IN_PROGRESS));
+          final @NotNull CheckIn inProgress = new CheckIn(monitorSlug, CheckInStatus.IN_PROGRESS);
+          inProgress.setMonitorConfig(monitorConfig);
+          checkInId = scopes.captureCheckIn(inProgress);
         }
         return invocation.proceed();
       } catch (Throwable e) {
@@ -113,6 +140,96 @@ public Object invoke(final @NotNull MethodInvocation invocation) throws Throwabl
     }
   }
 
+  private @Nullable MonitorConfig monitorConfig(final @NotNull Method method) {
+    return monitorConfigs.computeIfAbsent(
+            method, key -> new CachedMonitorConfig(monitorConfigFromScheduled(key)))
+        .config;
+  }
+
+  private @Nullable MonitorConfig monitorConfigFromScheduled(final @NotNull Method method) {
+    try {
+      final @NotNull Set<Scheduled> schedules =
+          AnnotatedElementUtils.findMergedRepeatableAnnotations(method, Scheduled.class);
+      if (schedules.size() != 1) {
+        return null;
+      }
+      final @NotNull Scheduled scheduled = schedules.iterator().next();
+      // timeUnit only exists from Spring 5.3.10, so read it as an attribute
+      final @Nullable Object timeUnitAttribute =
+          AnnotationUtils.getAnnotationAttributes(scheduled).get("timeUnit");
+      final @NotNull TimeUnit timeUnit =
+          timeUnitAttribute instanceof TimeUnit
+              ? (TimeUnit) timeUnitAttribute
+              : TimeUnit.MILLISECONDS;
+      final @Nullable String cron = resolve(scheduled.cron());
+      // Spring only reads the zone for a cron
+      final @Nullable String zone =
+          cron == null || cron.isEmpty() ? null : resolve(scheduled.zone());
+      return MonitorConfigUtils.fromSpringScheduled(
+          cron,
+          zone,
+          periodMillis(scheduled.fixedRate(), scheduled.fixedRateString(), timeUnit),
+          periodMillis(scheduled.fixedDelay(), scheduled.fixedDelayString(), timeUnit),
+          LEGACY_CRON_PARSER);
+    } catch (RuntimeException e) {
+      scopes
+          .getOptions()
+          .getLogger()
+          .log(
+              SentryLevel.WARNING,
+              "Could not derive a monitor config from @Scheduled for method annotated with @SentryCheckIn.",
+              e);
+      return null;
+    }
+  }
+
+  private @Nullable Long periodMillis(
+      final long value, final @NotNull String valueString, final @NotNull TimeUnit timeUnit) {
+    if (value >= 0) {
+      return timeUnit.toMillis(value);
+    }
+    final @Nullable String resolved = resolve(valueString);
+    if (resolved == null || resolved.isEmpty()) {
+      return null;
+    }
+    final @NotNull String trimmed = resolved.trim();
+    @Nullable Long millis = null;
+    if (trimmed.startsWith("P") || trimmed.startsWith("p")) {
+      try {
+        millis = Duration.parse(trimmed).toMillis();
+      } catch (DateTimeParseException | ArithmeticException e) {
+        // logged below
+      }
+    } else {
+      millis = MonitorConfigUtils.parsePeriodMillis(trimmed, timeUnit);
+    }
+    if (millis == null) {
+      scopes
+          .getOptions()
+          .getLogger()
+          .log(
+              SentryLevel.DEBUG,
+              "Not sending a monitor config for @SentryCheckIn because the @Scheduled period '%s' could not be parsed.",
+              trimmed);
+    }
+    return millis;
+  }
+
+  private @Nullable String resolve(final @NotNull String value) {
+    if (resolver == null || value.isEmpty()) {
+      return value;
+    }
+    return resolver.resolveStringValue(value);
+  }
+
+  private static final class CachedMonitorConfig {
+    private final @Nullable MonitorConfig config;
+
+    private CachedMonitorConfig(final @Nullable MonitorConfig config) {
+      this.config = config;
+    }
+  }
+
   @Override
   public void setEmbeddedValueResolver(StringValueResolver resolver) {
     this.resolver = resolver;
diff --git a/sentry-spring-jakarta/src/test/kotlin/io/sentry/spring/jakarta/SentryCheckInAdviceTest.kt b/sentry-spring-jakarta/src/test/kotlin/io/sentry/spring/jakarta/SentryCheckInAdviceTest.kt
index c6edd834530..7a7e5b81d04 100644
--- a/sentry-spring-jakarta/src/test/kotlin/io/sentry/spring/jakarta/SentryCheckInAdviceTest.kt
+++ b/sentry-spring-jakarta/src/test/kotlin/io/sentry/spring/jakarta/SentryCheckInAdviceTest.kt
@@ -4,16 +4,21 @@ import io.sentry.CheckIn
 import io.sentry.CheckInStatus
 import io.sentry.IScopes
 import io.sentry.ISentryLifecycleToken
+import io.sentry.MonitorConfig
 import io.sentry.Sentry
 import io.sentry.SentryOptions
 import io.sentry.protocol.SentryId
 import io.sentry.spring.jakarta.checkin.SentryCheckIn
 import io.sentry.spring.jakarta.checkin.SentryCheckInAdviceConfiguration
 import io.sentry.spring.jakarta.checkin.SentryCheckInPointcutConfiguration
+import java.util.TimeZone
+import java.util.concurrent.TimeUnit
 import kotlin.test.BeforeTest
 import kotlin.test.Test
 import kotlin.test.assertEquals
 import kotlin.test.assertNotNull
+import kotlin.test.assertNull
+import kotlin.test.assertSame
 import org.junit.jupiter.api.assertThrows
 import org.junit.runner.RunWith
 import org.mockito.kotlin.any
@@ -32,6 +37,8 @@ import org.springframework.context.annotation.Configuration
 import org.springframework.context.annotation.EnableAspectJAutoProxy
 import org.springframework.context.annotation.Import
 import org.springframework.context.support.PropertySourcesPlaceholderConfigurer
+import org.springframework.scheduling.annotation.Scheduled
+import org.springframework.scheduling.annotation.Schedules
 import org.springframework.test.context.TestPropertySource
 import org.springframework.test.context.junit.jupiter.SpringJUnitConfig
 import org.springframework.test.context.junit4.SpringRunner
@@ -39,7 +46,15 @@ import org.springframework.util.StringValueResolver
 
 @RunWith(SpringRunner::class)
 @SpringJUnitConfig(SentryCheckInAdviceTest.Config::class)
-@TestPropertySource(properties = ["my.cron.slug = mypropertycronslug"])
+@TestPropertySource(
+  properties =
+    [
+      "my.cron.slug = mypropertycronslug",
+      "my.cron.schedule = 0 30 2 * * *",
+      "my.cron.zone = America/New_York",
+      "my.cron.empty.zone = ",
+    ]
+)
 class SentryCheckInAdviceTest {
 
   @Autowired lateinit var sampleService: SampleService
@@ -50,6 +65,8 @@ class SentryCheckInAdviceTest {
 
   @Autowired lateinit var sampleServiceSpringProperties: SampleServiceSpringProperties
 
+  @Autowired lateinit var sampleServiceScheduled: SampleServiceScheduled
+
   @Autowired lateinit var scopes: IScopes
 
   val lifecycleToken = mock<ISentryLifecycleToken>()
@@ -74,6 +91,7 @@ class SentryCheckInAdviceTest {
     val inProgressCheckIn = checkInCaptor.firstValue
     assertEquals("monitor_slug_1", inProgressCheckIn.monitorSlug)
     assertEquals(CheckInStatus.IN_PROGRESS.apiName(), inProgressCheckIn.status)
+    assertNull(inProgressCheckIn.monitorConfig)
 
     val doneCheckIn = checkInCaptor.lastValue
     assertEquals("monitor_slug_1", doneCheckIn.monitorSlug)
@@ -228,6 +246,150 @@ class SentryCheckInAdviceTest {
     order.verify(lifecycleToken).close()
   }
 
+  @Test
+  fun `cron with zone is sent as crontab monitor config`() {
+    val config = inProgressMonitorConfig { sampleServiceScheduled.cronWithZone() }
+    assertNotNull(config)
+    assertEquals("crontab", config.schedule.type)
+    assertEquals("15 10 * * 1-5", config.schedule.value)
+    assertNull(config.schedule.unit)
+    assertEquals("Europe/Vienna", config.timezone)
+  }
+
+  @Test
+  fun `cron without zone is sent in the JVM default zone`() {
+    val defaultTimeZone = TimeZone.getDefault()
+    TimeZone.setDefault(TimeZone.getTimeZone("Asia/Tokyo"))
+    try {
+      val config = inProgressMonitorConfig { sampleServiceScheduled.cron() }
+      assertEquals("0 2 * * *", config?.schedule?.value)
+      assertEquals("Asia/Tokyo", config?.timezone)
+    } finally {
+      TimeZone.setDefault(defaultTimeZone)
+    }
+  }
+
+  @Test
+  fun `cron and zone placeholders are resolved`() {
+    val config = inProgressMonitorConfig { sampleServiceScheduled.cronFromProperties() }
+    assertEquals("30 2 * * *", config?.schedule?.value)
+    assertEquals("America/New_York", config?.timezone)
+  }
+
+  @Test
+  fun `fixed rate with time unit is sent as interval monitor config`() {
+    val config = inProgressMonitorConfig { sampleServiceScheduled.fixedRateHours() }
+    assertNotNull(config)
+    assertEquals("interval", config.schedule.type)
+    assertEquals("2", config.schedule.value)
+    assertEquals("hour", config.schedule.unit)
+  }
+
+  @Test
+  fun `ISO-8601 fixed rate string is sent as interval monitor config`() {
+    val config = inProgressMonitorConfig { sampleServiceScheduled.fixedRateIso() }
+    assertEquals("10", config?.schedule?.value)
+    assertEquals("minute", config?.schedule?.unit)
+  }
+
+  @Test
+  fun `simple duration fixed rate string is sent as interval monitor config`() {
+    val config = inProgressMonitorConfig { sampleServiceScheduled.fixedRateSimpleDuration() }
+    assertEquals("interval", config?.schedule?.type)
+    assertEquals("5", config?.schedule?.value)
+    assertEquals("minute", config?.schedule?.unit)
+  }
+
+  @Test
+  fun `fixed delay sends no monitor config`() {
+    assertNull(inProgressMonitorConfig { sampleServiceScheduled.fixedDelay() })
+    assertNull(inProgressMonitorConfig { sampleServiceScheduled.fixedDelayIso() })
+  }
+
+  @Test
+  fun `disabled cron sends no monitor config`() {
+    assertNull(inProgressMonitorConfig { sampleServiceScheduled.disabledCron() })
+  }
+
+  @Test
+  fun `zone placeholder resolving to empty uses the JVM default zone`() {
+    val defaultTimeZone = TimeZone.getDefault()
+    TimeZone.setDefault(TimeZone.getTimeZone("Asia/Tokyo"))
+    try {
+      val config = inProgressMonitorConfig { sampleServiceScheduled.cronWithEmptyZone() }
+      assertEquals("0 3 * * *", config?.schedule?.value)
+      assertEquals("Asia/Tokyo", config?.timezone)
+    } finally {
+      TimeZone.setDefault(defaultTimeZone)
+    }
+  }
+
+  @Test
+  fun `cron zone overrides the default timezone from options`() {
+    val options =
+      SentryOptions().apply {
+        cron = SentryOptions.Cron().apply { defaultTimezone = "Europe/Berlin" }
+      }
+    whenever(scopes.options).thenReturn(options)
+    val config = inProgressMonitorConfig { sampleServiceScheduled.cronWithZoneAndDefaults() }
+    assertEquals("Europe/Vienna", config?.timezone)
+  }
+
+  @Test
+  fun `unresolvable cron placeholder sends no monitor config`() {
+    assertNull(inProgressMonitorConfig { sampleServiceScheduled.unresolvableCron() })
+  }
+
+  @Test
+  fun `exception while deriving monitor config sends no monitor config and runs the job`() {
+    var result = 0
+    assertNull(inProgressMonitorConfig { result = sampleServiceScheduled.derivationThrows() })
+    assertEquals(1, result)
+  }
+
+  @Test
+  fun `monitor config is derived once per method`() {
+    val first = inProgressMonitorConfig { sampleServiceScheduled.fixedRateHours() }
+    val second = inProgressMonitorConfig { sampleServiceScheduled.fixedRateHours() }
+    assertNotNull(first)
+    assertSame(first, second)
+  }
+
+  @Test
+  fun `multiple schedules send no monitor config`() {
+    assertNull(inProgressMonitorConfig { sampleServiceScheduled.multipleSchedules() })
+  }
+
+  @Test
+  fun `schedules container sends no monitor config`() {
+    assertNull(inProgressMonitorConfig { sampleServiceScheduled.schedulesContainer() })
+  }
+
+  @Test
+  fun `upsertMonitorConfig false sends no monitor config`() {
+    assertNull(inProgressMonitorConfig { sampleServiceScheduled.upsertDisabled() })
+  }
+
+  @Test
+  fun `heartbeat with @Scheduled sends a single check-in without monitor config`() {
+    val checkInCaptor = argumentCaptor<CheckIn>()
+    whenever(scopes.captureCheckIn(checkInCaptor.capture())).thenReturn(SentryId())
+    sampleServiceScheduled.heartbeat()
+    assertEquals(1, checkInCaptor.allValues.size)
+    assertEquals(CheckInStatus.OK.apiName(), checkInCaptor.firstValue.status)
+    assertNull(checkInCaptor.firstValue.monitorConfig)
+  }
+
+  private fun inProgressMonitorConfig(block: () -> Unit): MonitorConfig? {
+    val checkInCaptor = argumentCaptor<CheckIn>()
+    whenever(scopes.captureCheckIn(checkInCaptor.capture())).thenReturn(SentryId())
+    block()
+    assertEquals(2, checkInCaptor.allValues.size)
+    assertEquals(CheckInStatus.IN_PROGRESS.apiName(), checkInCaptor.firstValue.status)
+    assertNull(checkInCaptor.lastValue.monitorConfig)
+    return checkInCaptor.firstValue.monitorConfig
+  }
+
   @Configuration
   @EnableAspectJAutoProxy(proxyTargetClass = true)
   @Import(SentryCheckInAdviceConfiguration::class, SentryCheckInPointcutConfiguration::class)
@@ -241,6 +403,8 @@ class SentryCheckInAdviceTest {
 
     @Bean open fun sampleServiceSpringProperties() = SampleServiceSpringProperties()
 
+    @Bean open fun sampleServiceScheduled() = SampleServiceScheduled()
+
     @Bean
     open fun scopes(): IScopes {
       val scopes = mock<IScopes>()
@@ -291,6 +455,72 @@ class SentryCheckInAdviceTest {
     open fun helloExceptionProperty() = 1
   }
 
+  open class SampleServiceScheduled {
+
+    @SentryCheckIn("cron_zone")
+    @Scheduled(cron = "0 15 10 * * MON-FRI", zone = "Europe/Vienna")
+    open fun cronWithZone() {}
+
+    @SentryCheckIn("cron") @Scheduled(cron = "0 0 2 * * *") open fun cron() {}
+
+    @SentryCheckIn("cron_properties")
+    @Scheduled(cron = "\${my.cron.schedule}", zone = "\${my.cron.zone}")
+    open fun cronFromProperties() {}
+
+    @SentryCheckIn("fixed_rate_hours")
+    @Scheduled(fixedRate = 2, timeUnit = TimeUnit.HOURS)
+    open fun fixedRateHours() {}
+
+    @SentryCheckIn("fixed_rate_iso")
+    @Scheduled(fixedRateString = "PT10M")
+    open fun fixedRateIso() {}
+
+    @SentryCheckIn("fixed_rate_simple")
+    @Scheduled(fixedRateString = "5m")
+    open fun fixedRateSimpleDuration() {}
+
+    @SentryCheckIn("fixed_delay") @Scheduled(fixedDelay = 300_000) open fun fixedDelay() {}
+
+    @SentryCheckIn("fixed_delay_iso")
+    @Scheduled(fixedDelayString = "PT10M")
+    open fun fixedDelayIso() {}
+
+    @SentryCheckIn("disabled_cron") @Scheduled(cron = "-") open fun disabledCron() {}
+
+    @SentryCheckIn("cron_empty_zone")
+    @Scheduled(cron = "0 0 3 * * *", zone = "\${my.cron.empty.zone}")
+    open fun cronWithEmptyZone() {}
+
+    @SentryCheckIn("cron_zone_defaults")
+    @Scheduled(cron = "0 0 4 * * *", zone = "Europe/Vienna")
+    open fun cronWithZoneAndDefaults() {}
+
+    @SentryCheckIn("schedules_container")
+    @Schedules(Scheduled(cron = "0 0 1 * * *"), Scheduled(cron = "0 0 13 * * *"))
+    open fun schedulesContainer() {}
+
+    @SentryCheckIn("unresolvable_cron")
+    @Scheduled(cron = "\${my.cron.missing}")
+    open fun unresolvableCron() {}
+
+    @SentryCheckIn("derivation_throws")
+    @Scheduled(cron = "\${my.cron.exception.property}")
+    open fun derivationThrows() = 1
+
+    @SentryCheckIn("multiple")
+    @Scheduled(cron = "0 0 1 * * *")
+    @Scheduled(cron = "0 0 13 * * *")
+    open fun multipleSchedules() {}
+
+    @SentryCheckIn("upsert_disabled", upsertMonitorConfig = false)
+    @Scheduled(cron = "0 0 1 * * *")
+    open fun upsertDisabled() {}
+
+    @SentryCheckIn("heartbeat", heartbeat = true)
+    @Scheduled(cron = "0 0 1 * * *")
+    open fun heartbeat() {}
+  }
+
   class MyPropertyPlaceholderConfigurer : PropertySourcesPlaceholderConfigurer() {
 
     override fun doProcessProperties(
diff --git a/sentry-spring/api/sentry-spring.api b/sentry-spring/api/sentry-spring.api
index 4e1bea84288..8b8bfa69c70 100644
--- a/sentry-spring/api/sentry-spring.api
+++ b/sentry-spring/api/sentry-spring.api
@@ -134,6 +134,7 @@ public final class io/sentry/spring/cache/SentryCacheWrapper : org/springframewo
 public abstract interface annotation class io/sentry/spring/checkin/SentryCheckIn : java/lang/annotation/Annotation {
 	public abstract fun heartbeat ()Z
 	public abstract fun monitorSlug ()Ljava/lang/String;
+	public abstract fun upsertMonitorConfig ()Z
 	public abstract fun value ()Ljava/lang/String;
 }
 
diff --git a/sentry-spring/src/main/java/io/sentry/spring/checkin/SentryCheckIn.java b/sentry-spring/src/main/java/io/sentry/spring/checkin/SentryCheckIn.java
index 805f4bd5464..03df99385c2 100644
--- a/sentry-spring/src/main/java/io/sentry/spring/checkin/SentryCheckIn.java
+++ b/sentry-spring/src/main/java/io/sentry/spring/checkin/SentryCheckIn.java
@@ -29,6 +29,17 @@
    */
   boolean heartbeat() default false;
 
+  /**
+   * Whether to send the schedule and zone from the method's {@code @Scheduled} with check-ins, so
+   * Sentry creates or updates the monitor. On by default. Set to false to manage the monitor's
+   * schedule in Sentry instead.
+   *
+   * <p>Heartbeat check-ins never send a monitor config.
+   *
+   * @return true to send a monitor config, true by default
+   */
+  boolean upsertMonitorConfig() default true;
+
   /**
    * Monitor slug. If not set, no check-in will be sent.
    *
diff --git a/sentry-spring/src/main/java/io/sentry/spring/checkin/SentryCheckInAdvice.java b/sentry-spring/src/main/java/io/sentry/spring/checkin/SentryCheckInAdvice.java
index 2abd2cfb994..202bd30e56a 100644
--- a/sentry-spring/src/main/java/io/sentry/spring/checkin/SentryCheckInAdvice.java
+++ b/sentry-spring/src/main/java/io/sentry/spring/checkin/SentryCheckInAdvice.java
@@ -6,13 +6,21 @@
 import io.sentry.DateUtils;
 import io.sentry.IScopes;
 import io.sentry.ISentryLifecycleToken;
+import io.sentry.MonitorConfig;
 import io.sentry.ScopesAdapter;
 import io.sentry.SentryLevel;
 import io.sentry.protocol.SentryId;
 import io.sentry.time.Stopwatch;
+import io.sentry.util.MonitorConfigUtils;
 import io.sentry.util.Objects;
 import io.sentry.util.TracingUtils;
 import java.lang.reflect.Method;
+import java.time.Duration;
+import java.time.format.DateTimeParseException;
+import java.util.Map;
+import java.util.Set;
+import java.util.concurrent.ConcurrentHashMap;
+import java.util.concurrent.TimeUnit;
 import org.aopalliance.intercept.MethodInterceptor;
 import org.aopalliance.intercept.MethodInvocation;
 import org.jetbrains.annotations.ApiStatus;
@@ -20,7 +28,10 @@
 import org.jetbrains.annotations.Nullable;
 import org.springframework.aop.support.AopUtils;
 import org.springframework.context.EmbeddedValueResolverAware;
+import org.springframework.core.annotation.AnnotatedElementUtils;
 import org.springframework.core.annotation.AnnotationUtils;
+import org.springframework.scheduling.annotation.Scheduled;
+import org.springframework.util.ClassUtils;
 import org.springframework.util.ObjectUtils;
 import org.springframework.util.StringValueResolver;
 
@@ -31,10 +42,19 @@
 @ApiStatus.Internal
 @Open
 public class SentryCheckInAdvice implements MethodInterceptor, EmbeddedValueResolverAware {
+  // Spring before 5.3 parses crons with CronSequenceGenerator
+  private static final boolean LEGACY_CRON_PARSER =
+      !ClassUtils.isPresent(
+          "org.springframework.scheduling.support.CronExpression",
+          SentryCheckInAdvice.class.getClassLoader());
+
   private final @NotNull IScopes scopes;
 
   private @Nullable StringValueResolver resolver;
 
+  private final @NotNull Map<Method, CachedMonitorConfig> monitorConfigs =
+      new ConcurrentHashMap<>();
+
   public SentryCheckInAdvice() {
     this(ScopesAdapter.getInstance());
   }
@@ -90,6 +110,11 @@ public Object invoke(final @NotNull MethodInvocation invocation) throws Throwabl
       return invocation.proceed();
     }
 
+    final @Nullable MonitorConfig monitorConfig =
+        !isHeartbeatOnly && checkInAnnotation.upsertMonitorConfig()
+            ? monitorConfig(mostSpecificMethod)
+            : null;
+
     try (final @NotNull ISentryLifecycleToken ignored =
             scopes.forkedScopes("SentryCheckInAdvice").makeCurrent()) {
       TracingUtils.startNewTrace(scopes);
@@ -101,7 +126,9 @@ public Object invoke(final @NotNull MethodInvocation invocation) throws Throwabl
 
       try {
         if (!isHeartbeatOnly) {
-          checkInId = scopes.captureCheckIn(new CheckIn(monitorSlug, CheckInStatus.IN_PROGRESS));
+          final @NotNull CheckIn inProgress = new CheckIn(monitorSlug, CheckInStatus.IN_PROGRESS);
+          inProgress.setMonitorConfig(monitorConfig);
+          checkInId = scopes.captureCheckIn(inProgress);
         }
         return invocation.proceed();
       } catch (Throwable e) {
@@ -116,6 +143,96 @@ public Object invoke(final @NotNull MethodInvocation invocation) throws Throwabl
     }
   }
 
+  private @Nullable MonitorConfig monitorConfig(final @NotNull Method method) {
+    return monitorConfigs.computeIfAbsent(
+            method, key -> new CachedMonitorConfig(monitorConfigFromScheduled(key)))
+        .config;
+  }
+
+  private @Nullable MonitorConfig monitorConfigFromScheduled(final @NotNull Method method) {
+    try {
+      final @NotNull Set<Scheduled> schedules =
+          AnnotatedElementUtils.findMergedRepeatableAnnotations(method, Scheduled.class);
+      if (schedules.size() != 1) {
+        return null;
+      }
+      final @NotNull Scheduled scheduled = schedules.iterator().next();
+      // timeUnit only exists from Spring 5.3.10, so read it as an attribute
+      final @Nullable Object timeUnitAttribute =
+          AnnotationUtils.getAnnotationAttributes(scheduled).get("timeUnit");
+      final @NotNull TimeUnit timeUnit =
+          timeUnitAttribute instanceof TimeUnit
+              ? (TimeUnit) timeUnitAttribute
+              : TimeUnit.MILLISECONDS;
+      final @Nullable String cron = resolve(scheduled.cron());
+      // Spring only reads the zone for a cron
+      final @Nullable String zone =
+          cron == null || cron.isEmpty() ? null : resolve(scheduled.zone());
+      return MonitorConfigUtils.fromSpringScheduled(
+          cron,
+          zone,
+          periodMillis(scheduled.fixedRate(), scheduled.fixedRateString(), timeUnit),
+          periodMillis(scheduled.fixedDelay(), scheduled.fixedDelayString(), timeUnit),
+          LEGACY_CRON_PARSER);
+    } catch (RuntimeException e) {
+      scopes
+          .getOptions()
+          .getLogger()
+          .log(
+              SentryLevel.WARNING,
+              "Could not derive a monitor config from @Scheduled for method annotated with @SentryCheckIn.",
+              e);
+      return null;
+    }
+  }
+
+  private @Nullable Long periodMillis(
+      final long value, final @NotNull String valueString, final @NotNull TimeUnit timeUnit) {
+    if (value >= 0) {
+      return timeUnit.toMillis(value);
+    }
+    final @Nullable String resolved = resolve(valueString);
+    if (resolved == null || resolved.isEmpty()) {
+      return null;
+    }
+    final @NotNull String trimmed = resolved.trim();
+    @Nullable Long millis = null;
+    if (trimmed.startsWith("P") || trimmed.startsWith("p")) {
+      try {
+        millis = Duration.parse(trimmed).toMillis();
+      } catch (DateTimeParseException | ArithmeticException e) {
+        // logged below
+      }
+    } else {
+      millis = MonitorConfigUtils.parsePeriodMillis(trimmed, timeUnit);
+    }
+    if (millis == null) {
+      scopes
+          .getOptions()
+          .getLogger()
+          .log(
+              SentryLevel.DEBUG,
+              "Not sending a monitor config for @SentryCheckIn because the @Scheduled period '%s' could not be parsed.",
+              trimmed);
+    }
+    return millis;
+  }
+
+  private @Nullable String resolve(final @NotNull String value) {
+    if (resolver == null || value.isEmpty()) {
+      return value;
+    }
+    return resolver.resolveStringValue(value);
+  }
+
+  private static final class CachedMonitorConfig {
+    private final @Nullable MonitorConfig config;
+
+    private CachedMonitorConfig(final @Nullable MonitorConfig config) {
+      this.config = config;
+    }
+  }
+
   @Override
   public void setEmbeddedValueResolver(StringValueResolver resolver) {
     this.resolver = resolver;
diff --git a/sentry-spring/src/test/kotlin/io/sentry/spring/SentryCheckInAdviceTest.kt b/sentry-spring/src/test/kotlin/io/sentry/spring/SentryCheckInAdviceTest.kt
index 2c5e7d0cd06..b6e8a4e3de2 100644
--- a/sentry-spring/src/test/kotlin/io/sentry/spring/SentryCheckInAdviceTest.kt
+++ b/sentry-spring/src/test/kotlin/io/sentry/spring/SentryCheckInAdviceTest.kt
@@ -4,17 +4,22 @@ import io.sentry.CheckIn
 import io.sentry.CheckInStatus
 import io.sentry.IScopes
 import io.sentry.ISentryLifecycleToken
+import io.sentry.MonitorConfig
 import io.sentry.Sentry
 import io.sentry.SentryOptions
 import io.sentry.protocol.SentryId
 import io.sentry.spring.checkin.SentryCheckIn
 import io.sentry.spring.checkin.SentryCheckInAdviceConfiguration
 import io.sentry.spring.checkin.SentryCheckInPointcutConfiguration
+import java.util.TimeZone
+import java.util.concurrent.TimeUnit
 import kotlin.RuntimeException
 import kotlin.test.BeforeTest
 import kotlin.test.Test
 import kotlin.test.assertEquals
 import kotlin.test.assertNotNull
+import kotlin.test.assertNull
+import kotlin.test.assertSame
 import org.junit.jupiter.api.assertThrows
 import org.junit.runner.RunWith
 import org.mockito.kotlin.any
@@ -33,6 +38,8 @@ import org.springframework.context.annotation.Configuration
 import org.springframework.context.annotation.EnableAspectJAutoProxy
 import org.springframework.context.annotation.Import
 import org.springframework.context.support.PropertySourcesPlaceholderConfigurer
+import org.springframework.scheduling.annotation.Scheduled
+import org.springframework.scheduling.annotation.Schedules
 import org.springframework.test.context.TestPropertySource
 import org.springframework.test.context.junit.jupiter.SpringJUnitConfig
 import org.springframework.test.context.junit4.SpringRunner
@@ -40,7 +47,15 @@ import org.springframework.util.StringValueResolver
 
 @RunWith(SpringRunner::class)
 @SpringJUnitConfig(SentryCheckInAdviceTest.Config::class)
-@TestPropertySource(properties = ["my.cron.slug = mypropertycronslug"])
+@TestPropertySource(
+  properties =
+    [
+      "my.cron.slug = mypropertycronslug",
+      "my.cron.schedule = 0 30 2 * * *",
+      "my.cron.zone = America/New_York",
+      "my.cron.empty.zone = ",
+    ]
+)
 class SentryCheckInAdviceTest {
 
   @Autowired lateinit var sampleService: SampleService
@@ -51,6 +66,8 @@ class SentryCheckInAdviceTest {
 
   @Autowired lateinit var sampleServiceSpringProperties: SampleServiceSpringProperties
 
+  @Autowired lateinit var sampleServiceScheduled: SampleServiceScheduled
+
   @Autowired lateinit var scopes: IScopes
 
   val lifecycleToken = mock<ISentryLifecycleToken>()
@@ -75,6 +92,7 @@ class SentryCheckInAdviceTest {
     val inProgressCheckIn = checkInCaptor.firstValue
     assertEquals("monitor_slug_1", inProgressCheckIn.monitorSlug)
     assertEquals(CheckInStatus.IN_PROGRESS.apiName(), inProgressCheckIn.status)
+    assertNull(inProgressCheckIn.monitorConfig)
 
     val doneCheckIn = checkInCaptor.lastValue
     assertEquals("monitor_slug_1", doneCheckIn.monitorSlug)
@@ -229,6 +247,150 @@ class SentryCheckInAdviceTest {
     order.verify(lifecycleToken).close()
   }
 
+  @Test
+  fun `cron with zone is sent as crontab monitor config`() {
+    val config = inProgressMonitorConfig { sampleServiceScheduled.cronWithZone() }
+    assertNotNull(config)
+    assertEquals("crontab", config.schedule.type)
+    assertEquals("15 10 * * 1-5", config.schedule.value)
+    assertNull(config.schedule.unit)
+    assertEquals("Europe/Vienna", config.timezone)
+  }
+
+  @Test
+  fun `cron without zone is sent in the JVM default zone`() {
+    val defaultTimeZone = TimeZone.getDefault()
+    TimeZone.setDefault(TimeZone.getTimeZone("Asia/Tokyo"))
+    try {
+      val config = inProgressMonitorConfig { sampleServiceScheduled.cron() }
+      assertEquals("0 2 * * *", config?.schedule?.value)
+      assertEquals("Asia/Tokyo", config?.timezone)
+    } finally {
+      TimeZone.setDefault(defaultTimeZone)
+    }
+  }
+
+  @Test
+  fun `cron and zone placeholders are resolved`() {
+    val config = inProgressMonitorConfig { sampleServiceScheduled.cronFromProperties() }
+    assertEquals("30 2 * * *", config?.schedule?.value)
+    assertEquals("America/New_York", config?.timezone)
+  }
+
+  @Test
+  fun `fixed rate with time unit is sent as interval monitor config`() {
+    val config = inProgressMonitorConfig { sampleServiceScheduled.fixedRateHours() }
+    assertNotNull(config)
+    assertEquals("interval", config.schedule.type)
+    assertEquals("2", config.schedule.value)
+    assertEquals("hour", config.schedule.unit)
+  }
+
+  @Test
+  fun `ISO-8601 fixed rate string is sent as interval monitor config`() {
+    val config = inProgressMonitorConfig { sampleServiceScheduled.fixedRateIso() }
+    assertEquals("10", config?.schedule?.value)
+    assertEquals("minute", config?.schedule?.unit)
+  }
+
+  @Test
+  fun `simple duration fixed rate string is sent as interval monitor config`() {
+    val config = inProgressMonitorConfig { sampleServiceScheduled.fixedRateSimpleDuration() }
+    assertEquals("interval", config?.schedule?.type)
+    assertEquals("5", config?.schedule?.value)
+    assertEquals("minute", config?.schedule?.unit)
+  }
+
+  @Test
+  fun `fixed delay sends no monitor config`() {
+    assertNull(inProgressMonitorConfig { sampleServiceScheduled.fixedDelay() })
+    assertNull(inProgressMonitorConfig { sampleServiceScheduled.fixedDelayIso() })
+  }
+
+  @Test
+  fun `disabled cron sends no monitor config`() {
+    assertNull(inProgressMonitorConfig { sampleServiceScheduled.disabledCron() })
+  }
+
+  @Test
+  fun `zone placeholder resolving to empty uses the JVM default zone`() {
+    val defaultTimeZone = TimeZone.getDefault()
+    TimeZone.setDefault(TimeZone.getTimeZone("Asia/Tokyo"))
+    try {
+      val config = inProgressMonitorConfig { sampleServiceScheduled.cronWithEmptyZone() }
+      assertEquals("0 3 * * *", config?.schedule?.value)
+      assertEquals("Asia/Tokyo", config?.timezone)
+    } finally {
+      TimeZone.setDefault(defaultTimeZone)
+    }
+  }
+
+  @Test
+  fun `cron zone overrides the default timezone from options`() {
+    val options =
+      SentryOptions().apply {
+        cron = SentryOptions.Cron().apply { defaultTimezone = "Europe/Berlin" }
+      }
+    whenever(scopes.options).thenReturn(options)
+    val config = inProgressMonitorConfig { sampleServiceScheduled.cronWithZoneAndDefaults() }
+    assertEquals("Europe/Vienna", config?.timezone)
+  }
+
+  @Test
+  fun `unresolvable cron placeholder sends no monitor config`() {
+    assertNull(inProgressMonitorConfig { sampleServiceScheduled.unresolvableCron() })
+  }
+
+  @Test
+  fun `exception while deriving monitor config sends no monitor config and runs the job`() {
+    var result = 0
+    assertNull(inProgressMonitorConfig { result = sampleServiceScheduled.derivationThrows() })
+    assertEquals(1, result)
+  }
+
+  @Test
+  fun `monitor config is derived once per method`() {
+    val first = inProgressMonitorConfig { sampleServiceScheduled.fixedRateHours() }
+    val second = inProgressMonitorConfig { sampleServiceScheduled.fixedRateHours() }
+    assertNotNull(first)
+    assertSame(first, second)
+  }
+
+  @Test
+  fun `multiple schedules send no monitor config`() {
+    assertNull(inProgressMonitorConfig { sampleServiceScheduled.multipleSchedules() })
+  }
+
+  @Test
+  fun `schedules container sends no monitor config`() {
+    assertNull(inProgressMonitorConfig { sampleServiceScheduled.schedulesContainer() })
+  }
+
+  @Test
+  fun `upsertMonitorConfig false sends no monitor config`() {
+    assertNull(inProgressMonitorConfig { sampleServiceScheduled.upsertDisabled() })
+  }
+
+  @Test
+  fun `heartbeat with @Scheduled sends a single check-in without monitor config`() {
+    val checkInCaptor = argumentCaptor<CheckIn>()
+    whenever(scopes.captureCheckIn(checkInCaptor.capture())).thenReturn(SentryId())
+    sampleServiceScheduled.heartbeat()
+    assertEquals(1, checkInCaptor.allValues.size)
+    assertEquals(CheckInStatus.OK.apiName(), checkInCaptor.firstValue.status)
+    assertNull(checkInCaptor.firstValue.monitorConfig)
+  }
+
+  private fun inProgressMonitorConfig(block: () -> Unit): MonitorConfig? {
+    val checkInCaptor = argumentCaptor<CheckIn>()
+    whenever(scopes.captureCheckIn(checkInCaptor.capture())).thenReturn(SentryId())
+    block()
+    assertEquals(2, checkInCaptor.allValues.size)
+    assertEquals(CheckInStatus.IN_PROGRESS.apiName(), checkInCaptor.firstValue.status)
+    assertNull(checkInCaptor.lastValue.monitorConfig)
+    return checkInCaptor.firstValue.monitorConfig
+  }
+
   @Configuration
   @EnableAspectJAutoProxy(proxyTargetClass = true)
   @Import(SentryCheckInAdviceConfiguration::class, SentryCheckInPointcutConfiguration::class)
@@ -242,6 +404,8 @@ class SentryCheckInAdviceTest {
 
     @Bean open fun sampleServiceSpringProperties() = SampleServiceSpringProperties()
 
+    @Bean open fun sampleServiceScheduled() = SampleServiceScheduled()
+
     @Bean
     open fun scopes(): IScopes {
       val scopes = mock<IScopes>()
@@ -292,6 +456,72 @@ class SentryCheckInAdviceTest {
     open fun helloExceptionProperty() = 1
   }
 
+  open class SampleServiceScheduled {
+
+    @SentryCheckIn("cron_zone")
+    @Scheduled(cron = "0 15 10 * * MON-FRI", zone = "Europe/Vienna")
+    open fun cronWithZone() {}
+
+    @SentryCheckIn("cron") @Scheduled(cron = "0 0 2 * * *") open fun cron() {}
+
+    @SentryCheckIn("cron_properties")
+    @Scheduled(cron = "\${my.cron.schedule}", zone = "\${my.cron.zone}")
+    open fun cronFromProperties() {}
+
+    @SentryCheckIn("fixed_rate_hours")
+    @Scheduled(fixedRate = 2, timeUnit = TimeUnit.HOURS)
+    open fun fixedRateHours() {}
+
+    @SentryCheckIn("fixed_rate_iso")
+    @Scheduled(fixedRateString = "PT10M")
+    open fun fixedRateIso() {}
+
+    @SentryCheckIn("fixed_rate_simple")
+    @Scheduled(fixedRateString = "5m")
+    open fun fixedRateSimpleDuration() {}
+
+    @SentryCheckIn("fixed_delay") @Scheduled(fixedDelay = 300_000) open fun fixedDelay() {}
+
+    @SentryCheckIn("fixed_delay_iso")
+    @Scheduled(fixedDelayString = "PT10M")
+    open fun fixedDelayIso() {}
+
+    @SentryCheckIn("disabled_cron") @Scheduled(cron = "-") open fun disabledCron() {}
+
+    @SentryCheckIn("cron_empty_zone")
+    @Scheduled(cron = "0 0 3 * * *", zone = "\${my.cron.empty.zone}")
+    open fun cronWithEmptyZone() {}
+
+    @SentryCheckIn("cron_zone_defaults")
+    @Scheduled(cron = "0 0 4 * * *", zone = "Europe/Vienna")
+    open fun cronWithZoneAndDefaults() {}
+
+    @SentryCheckIn("schedules_container")
+    @Schedules(Scheduled(cron = "0 0 1 * * *"), Scheduled(cron = "0 0 13 * * *"))
+    open fun schedulesContainer() {}
+
+    @SentryCheckIn("unresolvable_cron")
+    @Scheduled(cron = "\${my.cron.missing}")
+    open fun unresolvableCron() {}
+
+    @SentryCheckIn("derivation_throws")
+    @Scheduled(cron = "\${my.cron.exception.property}")
+    open fun derivationThrows() = 1
+
+    @SentryCheckIn("multiple")
+    @Scheduled(cron = "0 0 1 * * *")
+    @Scheduled(cron = "0 0 13 * * *")
+    open fun multipleSchedules() {}
+
+    @SentryCheckIn("upsert_disabled", upsertMonitorConfig = false)
+    @Scheduled(cron = "0 0 1 * * *")
+    open fun upsertDisabled() {}
+
+    @SentryCheckIn("heartbeat", heartbeat = true)
+    @Scheduled(cron = "0 0 1 * * *")
+    open fun heartbeat() {}
+  }
+
   class MyPropertyPlaceholderConfigurer : PropertySourcesPlaceholderConfigurer() {
 
     override fun doProcessProperties(