diff --git a/CHANGELOG.md b/CHANGELOG.md
index 3494f6f76d..cab90eb6b1 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -5,6 +5,7 @@
 **Fixes**:
 
 - Crashpad: wait reliably for crash report uploads. ([#1885](https://github.com/getsentry/sentry-native/pull/1885))
+- Android: create the outbox directory before writing NDK crash envelopes into it, so envelopes are not lost when the head SDK creates the outbox lazily. ([#1889](https://github.com/getsentry/sentry-native/pull/1889))
 
 ## 0.15.4
 
diff --git a/ndk/lib/CMakeLists.txt b/ndk/lib/CMakeLists.txt
index 9bef5d7b3b..1b4153eda8 100644
--- a/ndk/lib/CMakeLists.txt
+++ b/ndk/lib/CMakeLists.txt
@@ -27,7 +27,10 @@ if(ENABLE_TESTS)
 endif()
 
 # Link to sentry-native
-target_link_libraries(sentry-android PRIVATE $<BUILD_INTERFACE:sentry::sentry>)
+target_link_libraries(sentry-android PRIVATE
+	${LOG_LIB}
+	$<BUILD_INTERFACE:sentry::sentry>
+)
 
 # Support 16KB page sizes
 target_link_options(sentry-android PRIVATE "-Wl,-z,max-page-size=16384")
diff --git a/ndk/lib/src/main/jni/sentry.c b/ndk/lib/src/main/jni/sentry.c
index 2af6fc9cf8..8235a77824 100644
--- a/ndk/lib/src/main/jni/sentry.c
+++ b/ndk/lib/src/main/jni/sentry.c
@@ -1,8 +1,11 @@
+#include <android/log.h>
+#include <errno.h>
 #include <jni.h>
 #include <sentry.h>
 #include <stdbool.h>
 #include <stdio.h>
 #include <string.h>
+#include <sys/stat.h>
 
 #define ENSURE(Expr)                                                           \
     if (!(Expr))                                                               \
@@ -308,6 +311,38 @@ Java_io_sentry_ndk_NativeScope_nativeClearAttachments(JNIEnv *env, jclass cls)
     sentry_clear_attachments();
 }
 
+// sentry-native's path helpers are internal to the core library and not
+// exported from the shared object we link against, so we create the outbox
+// ourselves. Android is always POSIX, so mkdir(2) is all we need.
+static int
+create_dir_all(const char *path)
+{
+    char *buf = sentry_malloc(strlen(path) + 1);
+    if (!buf) {
+        return -1;
+    }
+    strcpy(buf, path);
+
+    int rv = 0;
+    for (char *p = buf; *p; p++) {
+        if (*p == '/' && p != buf) {
+            *p = '\0';
+            if (mkdir(buf, 0700) != 0 && errno != EEXIST && errno != EINVAL) {
+                rv = -1;
+                goto done;
+            }
+            *p = '/';
+        }
+    }
+    if (mkdir(buf, 0700) != 0 && errno != EEXIST && errno != EINVAL) {
+        rv = -1;
+    }
+
+done:
+    sentry_free(buf);
+    return rv;
+}
+
 static void
 send_envelope(sentry_envelope_t *envelope, void *data)
 {
@@ -317,6 +352,14 @@ send_envelope(sentry_envelope_t *envelope, void *data)
     sentry_uuid_t envelope_id = sentry_uuid_new_v4();
     sentry_uuid_as_string(&envelope_id, envelope_id_str);
 
+    // The head SDK may create the outbox lazily, so ensure it exists before
+    // writing into it; the underlying file write does not create parent
+    // directories and would otherwise silently fail.
+    if (create_dir_all(outbox_path) != 0) {
+        __android_log_print(ANDROID_LOG_ERROR, "sentry-native",
+            "failed to create outbox directory \"%s\"", outbox_path);
+    }
+
     size_t outbox_len = strlen(outbox_path);
     size_t final_len = outbox_len + 42; // "/" + envelope_id_str + "\0" = 42
     char *envelope_path = sentry_malloc(final_len);
diff --git a/ndk/sample/src/main/java/io/sentry/ndk/sample/MainActivity.java b/ndk/sample/src/main/java/io/sentry/ndk/sample/MainActivity.java
index fdef19d5aa..92d07b63d0 100644
--- a/ndk/sample/src/main/java/io/sentry/ndk/sample/MainActivity.java
+++ b/ndk/sample/src/main/java/io/sentry/ndk/sample/MainActivity.java
@@ -19,7 +19,9 @@ protected void onCreate(Bundle savedInstanceState) {
   }
 
   private void initNdk() {
-    final File outboxFolder = setupOutboxFolder();
+    // The outbox directory is created by sentry-native, so we only need to
+    // hand it the path here.
+    final File outboxFolder = new File(getFilesDir(), "outbox");
     final NdkOptions options =
         new NdkOptions(
             "https://1053864c67cc410aa1ffc9701bd6f93d@o447951.ingest.sentry.io/5428559",
@@ -34,22 +36,4 @@ private void initNdk() {
     options.setTracesSampleRate(1);
     SentryNdk.init(options);
   }
-
-  private File setupOutboxFolder() {
-    // ensure we have a proper outbox directory
-    final File outboxDir = new File(getFilesDir(), "outbox");
-    if (outboxDir.isFile()) {
-      final boolean deleteOk = outboxDir.delete();
-      if (!deleteOk) {
-        throw new IllegalStateException("Failed to delete outbox file: " + outboxDir);
-      }
-    }
-    if (!outboxDir.exists()) {
-      final boolean mkdirOk = outboxDir.mkdirs();
-      if (!mkdirOk) {
-        throw new IllegalStateException("Failed to create outbox directory: " + outboxDir);
-      }
-    }
-    return outboxDir;
-  }
 }