diff --git a/sentry/src/main/java/io/sentry/MonitorContexts.java b/sentry/src/main/java/io/sentry/MonitorContexts.java
index 193d9ee5a6..af8a963f63 100644
--- a/sentry/src/main/java/io/sentry/MonitorContexts.java
+++ b/sentry/src/main/java/io/sentry/MonitorContexts.java
@@ -3,8 +3,7 @@
 import io.sentry.util.Objects;
 import io.sentry.vendor.gson.stream.JsonToken;
 import java.io.IOException;
-import java.util.Collections;
-import java.util.List;
+import java.util.Arrays;
 import java.util.concurrent.ConcurrentHashMap;
 import org.jetbrains.annotations.NotNull;
 import org.jetbrains.annotations.Nullable;
@@ -12,6 +11,7 @@
 public final class MonitorContexts extends ConcurrentHashMap<String, Object>
     implements JsonSerializable {
   private static final long serialVersionUID = 3987329379811822556L;
+  private static final String[] EMPTY_KEYS = new String[0];
 
   public MonitorContexts() {}
 
@@ -49,8 +49,8 @@ public void serialize(final @NotNull ObjectWriter writer, final @NotNull ILogger
       throws IOException {
     writer.beginObject();
     // Serialize in alphabetical order to keep determinism.
-    final List<String> sortedKeys = Collections.list(keys());
-    Collections.sort(sortedKeys);
+    final String[] sortedKeys = keySet().toArray(EMPTY_KEYS);
+    Arrays.sort(sortedKeys);
     for (final String key : sortedKeys) {
       final Object value = get(key);
       if (value != null) {
diff --git a/sentry/src/main/java/io/sentry/protocol/Contexts.java b/sentry/src/main/java/io/sentry/protocol/Contexts.java
index fd1e9b83eb..82f70bb712 100644
--- a/sentry/src/main/java/io/sentry/protocol/Contexts.java
+++ b/sentry/src/main/java/io/sentry/protocol/Contexts.java
@@ -14,10 +14,9 @@
 import io.sentry.util.Objects;
 import io.sentry.vendor.gson.stream.JsonToken;
 import java.io.IOException;
-import java.util.Collections;
+import java.util.Arrays;
 import java.util.Enumeration;
 import java.util.HashMap;
-import java.util.List;
 import java.util.Map;
 import java.util.Set;
 import java.util.concurrent.ConcurrentHashMap;
@@ -28,6 +27,7 @@
 public class Contexts implements JsonSerializable {
   private static final long serialVersionUID = 252445813254943011L;
   public static final String REPLAY_ID = "replay_id";
+  private static final String[] EMPTY_KEYS = new String[0];
 
   private final @NotNull ConcurrentHashMap<String, Object> internalStorage =
       new ConcurrentHashMap<>();
@@ -302,8 +302,8 @@ public void serialize(final @NotNull ObjectWriter writer, final @NotNull ILogger
       throws IOException {
     writer.beginObject();
     // Serialize in alphabetical order to keep determinism.
-    final List<String> sortedKeys = Collections.list(keys());
-    Collections.sort(sortedKeys);
+    final String[] sortedKeys = internalStorage.keySet().toArray(EMPTY_KEYS);
+    Arrays.sort(sortedKeys);
     for (final String key : sortedKeys) {
       final Object value = get(key);
       if (value != null) {
diff --git a/sentry/src/test/java/io/sentry/MonitorContextsTest.kt b/sentry/src/test/java/io/sentry/MonitorContextsTest.kt
new file mode 100644
index 0000000000..2b0d57e605
--- /dev/null
+++ b/sentry/src/test/java/io/sentry/MonitorContextsTest.kt
@@ -0,0 +1,19 @@
+package io.sentry
+
+import io.sentry.protocol.SerializationUtils
+import kotlin.test.Test
+import kotlin.test.assertEquals
+import org.mockito.kotlin.mock
+
+class MonitorContextsTest {
+  @Test
+  fun `serializes entries in alphabetical order`() {
+    val contexts =
+      MonitorContexts().apply {
+        put("b", 2)
+        put("a", 1)
+      }
+
+    assertEquals("{\"a\":1,\"b\":2}", SerializationUtils.serializeToString(contexts, mock()))
+  }
+}