diff --git a/ci/images/releasescripts/pom.xml b/ci/images/releasescripts/pom.xml
index 6dc3a70680c..05bd6dde8e9 100644
--- a/ci/images/releasescripts/pom.xml
+++ b/ci/images/releasescripts/pom.xml
@@ -44,6 +44,10 @@
 			<groupId>com.fasterxml.jackson.module</groupId>
 			<artifactId>jackson-module-parameter-names</artifactId>
 		</dependency>
+		<dependency>
+			<groupId>org.awaitility</groupId>
+			<artifactId>awaitility</artifactId>
+		</dependency>
 		<dependency>
 			<groupId>org.springframework.boot</groupId>
 			<artifactId>spring-boot-starter-test</artifactId>
diff --git a/ci/images/releasescripts/src/main/java/io/spring/concourse/releasescripts/bintray/BintrayService.java b/ci/images/releasescripts/src/main/java/io/spring/concourse/releasescripts/bintray/BintrayService.java
index f3ee0d9cd41..c5b38b74bb2 100644
--- a/ci/images/releasescripts/src/main/java/io/spring/concourse/releasescripts/bintray/BintrayService.java
+++ b/ci/images/releasescripts/src/main/java/io/spring/concourse/releasescripts/bintray/BintrayService.java
@@ -17,19 +17,25 @@
 package io.spring.concourse.releasescripts.bintray;
 
 import java.net.URI;
+import java.util.Objects;
+import java.util.concurrent.TimeUnit;
 
 import io.spring.concourse.releasescripts.ReleaseInfo;
 import io.spring.concourse.releasescripts.sonatype.SonatypeProperties;
 import io.spring.concourse.releasescripts.sonatype.SonatypeService;
 import io.spring.concourse.releasescripts.system.ConsoleLogger;
+import org.awaitility.core.ConditionTimeoutException;
 
 import org.springframework.boot.web.client.RestTemplateBuilder;
+import org.springframework.http.HttpStatus;
 import org.springframework.http.MediaType;
 import org.springframework.http.RequestEntity;
 import org.springframework.stereotype.Component;
 import org.springframework.web.client.HttpClientErrorException;
 import org.springframework.web.client.RestTemplate;
 
+import static org.awaitility.Awaitility.waitAtMost;
+
 /**
  * Central class for interacting with Bintray's REST API.
  *
@@ -64,25 +70,29 @@ public class BintrayService {
 	}
 
 	public boolean isDistributionComplete(ReleaseInfo releaseInfo) {
-		RequestEntity<Void> publishedFilesRequest = getRequest(releaseInfo, 0);
 		RequestEntity<Void> allFilesRequest = getRequest(releaseInfo, 1);
-		Object[] allFiles = this.restTemplate.exchange(allFilesRequest, Object[].class).getBody();
-		int count = 0;
-		while (count < 120) {
-			Object[] publishedFiles = this.restTemplate.exchange(publishedFilesRequest, Object[].class).getBody();
-			int unpublished = allFiles.length - publishedFiles.length;
-			if (unpublished == 0) {
-				return true;
-			}
-			count++;
+		Object[] allFiles = waitAtMost(5, TimeUnit.MINUTES).with().pollDelay(20, TimeUnit.SECONDS).until(() -> {
 			try {
-				Thread.sleep(20000);
+				return this.restTemplate.exchange(allFilesRequest, Object[].class).getBody();
 			}
-			catch (InterruptedException e) {
-
+			catch (HttpClientErrorException ex) {
+				if (ex.getStatusCode() != HttpStatus.NOT_FOUND) {
+					throw ex;
+				}
+				return null;
 			}
+		}, Objects::nonNull);
+		RequestEntity<Void> publishedFilesRequest = getRequest(releaseInfo, 0);
+		try {
+			waitAtMost(40, TimeUnit.MINUTES).with().pollDelay(20, TimeUnit.SECONDS).until(() -> {
+				Object[] publishedFiles = this.restTemplate.exchange(publishedFilesRequest, Object[].class).getBody();
+				return allFiles.length == publishedFiles.length;
+			});
 		}
-		return false;
+		catch (ConditionTimeoutException ex) {
+			return false;
+		}
+		return true;
 	}
 
 	private RequestEntity<Void> getRequest(ReleaseInfo releaseInfo, int includeUnpublished) {
diff --git a/ci/images/releasescripts/src/test/java/io/spring/concourse/releasescripts/bintray/BintrayServiceTests.java b/ci/images/releasescripts/src/test/java/io/spring/concourse/releasescripts/bintray/BintrayServiceTests.java
index 0cbccbe1494..e622ed3adb4 100644
--- a/ci/images/releasescripts/src/test/java/io/spring/concourse/releasescripts/bintray/BintrayServiceTests.java
+++ b/ci/images/releasescripts/src/test/java/io/spring/concourse/releasescripts/bintray/BintrayServiceTests.java
@@ -28,6 +28,7 @@ import org.springframework.boot.test.autoconfigure.web.client.RestClientTest;
 import org.springframework.boot.test.mock.mockito.MockBean;
 import org.springframework.core.io.ClassPathResource;
 import org.springframework.http.HttpMethod;
+import org.springframework.http.HttpStatus;
 import org.springframework.http.MediaType;
 import org.springframework.test.web.client.ExpectedCount;
 import org.springframework.test.web.client.MockRestServiceServer;
@@ -40,6 +41,7 @@ import static org.springframework.test.web.client.match.MockRestRequestMatchers.
 import static org.springframework.test.web.client.match.MockRestRequestMatchers.header;
 import static org.springframework.test.web.client.match.MockRestRequestMatchers.method;
 import static org.springframework.test.web.client.match.MockRestRequestMatchers.requestTo;
+import static org.springframework.test.web.client.response.MockRestResponseCreators.withStatus;
 import static org.springframework.test.web.client.response.MockRestResponseCreators.withSuccess;
 
 /**
@@ -73,6 +75,11 @@ class BintrayServiceTests {
 
 	@Test
 	void isDistributionComplete() throws Exception {
+		this.server
+				.expect(requestTo(String.format(
+						"https://api.bintray.com/packages/%s/%s/%s/versions/%s/files?include_unpublished=%s",
+						this.properties.getSubject(), this.properties.getRepo(), "example", "1.1.0.RELEASE", 1)))
+				.andRespond(withStatus(HttpStatus.NOT_FOUND));
 		setupGetPackageFiles(1, "all-package-files.json");
 		setupGetPackageFiles(0, "published-files.json");
 		setupGetPackageFiles(0, "all-package-files.json");