diff --git a/pom.xml b/pom.xml
index 56b9436d..ee9d1d02 100644
--- a/pom.xml
+++ b/pom.xml
@@ -111,6 +111,12 @@
         <classifier>tests</classifier>
         <scope>test</scope>
     </dependency>
+    <dependency>
+        <groupId>org.jenkins-ci.plugins.workflow</groupId>
+        <artifactId>workflow-step-api</artifactId>
+        <classifier>tests</classifier>
+        <scope>test</scope>
+    </dependency>
     <dependency>
       <groupId>org.jenkins-ci.test</groupId>
       <artifactId>docker-fixtures</artifactId>
diff --git a/src/main/java/io/jenkins/plugins/artifact_manager_jclouds/JCloudsArtifactManager.java b/src/main/java/io/jenkins/plugins/artifact_manager_jclouds/JCloudsArtifactManager.java
index 40fa42c6..56bc7814 100644
--- a/src/main/java/io/jenkins/plugins/artifact_manager_jclouds/JCloudsArtifactManager.java
+++ b/src/main/java/io/jenkins/plugins/artifact_manager_jclouds/JCloudsArtifactManager.java
@@ -121,7 +121,7 @@ private String getBlobPath(String key, String path) {
     public void archive(FilePath workspace, Launcher launcher, BuildListener listener, Map<String, String> artifacts)
             throws IOException, InterruptedException {
         LOGGER.log(Level.FINE, "Archiving from {0}: {1}", new Object[] { workspace, artifacts });
-        Map<String, String> contentTypes = workspace.act(new ContentTypeGuesser(new ArrayList<>(artifacts.keySet()), listener));
+        Map<String, String> contentTypes = workspace.act(new ContentTypeGuesser(new ArrayList<>(artifacts.values()), listener));
         LOGGER.fine(() -> "guessing content types: " + contentTypes);
         Map<String, URL> artifactUrls = new HashMap<>();
         BlobStore blobStore = getContext().getBlobStore();
@@ -132,7 +132,7 @@ public void archive(FilePath workspace, Launcher launcher, BuildListener listene
             String blobPath = getBlobPath(path);
             Blob blob = blobStore.blobBuilder(blobPath).build();
             blob.getMetadata().setContainer(provider.getContainer());
-            blob.getMetadata().getContentMetadata().setContentType(contentTypes.get(entry.getKey()));
+            blob.getMetadata().getContentMetadata().setContentType(contentTypes.get(entry.getValue()));
             artifactUrls.put(entry.getValue(), provider.toExternalURL(blob, HttpMethod.PUT));
         }
 
@@ -167,6 +167,8 @@ public Map<String, String> invoke(File f, VirtualChannel channel) {
                     contentTypes.put(relPath, contentType);
                 } catch (IOException e) {
                     Functions.printStackTrace(e, listener.error("Unable to determine content type for file: " + theFile));
+                    // A content type must be specified; otherwise, the metadata signature will be computed from data that includes "Content-Type:", but no such HTTP header will be sent, and AWS will reject the request.
+                    contentTypes.put(relPath, "application/octet-stream");
                 }
             }
             return contentTypes;
diff --git a/src/test/java/io/jenkins/plugins/artifact_manager_jclouds/s3/JCloudsArtifactManagerTest.java b/src/test/java/io/jenkins/plugins/artifact_manager_jclouds/s3/JCloudsArtifactManagerTest.java
index 3d290d5b..d67083ee 100644
--- a/src/test/java/io/jenkins/plugins/artifact_manager_jclouds/s3/JCloudsArtifactManagerTest.java
+++ b/src/test/java/io/jenkins/plugins/artifact_manager_jclouds/s3/JCloudsArtifactManagerTest.java
@@ -27,8 +27,11 @@
 import io.jenkins.plugins.artifact_manager_jclouds.BlobStoreProviderDescriptor;
 import io.jenkins.plugins.artifact_manager_jclouds.BlobStoreProvider;
 import io.jenkins.plugins.artifact_manager_jclouds.JCloudsArtifactManagerFactory;
+import static org.hamcrest.MatcherAssert.assertThat;
 import static org.hamcrest.Matchers.*;
-import static org.junit.Assert.*;
+import static org.junit.Assert.assertEquals;
+import static org.junit.Assert.assertTrue;
+import static org.junit.Assert.fail;
 import static org.junit.Assume.*;
 
 import java.io.IOException;
@@ -68,14 +71,18 @@
 import hudson.model.FreeStyleBuild;
 import hudson.model.FreeStyleProject;
 import hudson.model.Item;
+import hudson.model.Run;
+import hudson.model.TaskListener;
 import hudson.plugins.sshslaves.SSHLauncher;
 import hudson.remoting.Which;
 import hudson.slaves.DumbSlave;
 import hudson.tasks.ArtifactArchiver;
 import io.jenkins.plugins.aws.global_configuration.CredentialsAwsGlobalConfiguration;
+import java.io.Serializable;
 import java.net.URI;
 import java.net.URL;
 import java.util.Collections;
+import java.util.Set;
 import jenkins.branch.BranchSource;
 import jenkins.model.ArtifactManagerConfiguration;
 import jenkins.model.ArtifactManagerFactory;
@@ -84,6 +91,7 @@
 import jenkins.plugins.git.GitSampleRepoRule;
 import jenkins.plugins.git.traits.BranchDiscoveryTrait;
 import jenkins.security.MasterToSlaveCallable;
+import jenkins.util.BuildListenerAdapter;
 import org.jenkinsci.plugins.workflow.cps.CpsFlowDefinition;
 import org.jenkinsci.plugins.workflow.job.WorkflowJob;
 import org.jenkinsci.plugins.workflow.job.WorkflowRun;
@@ -93,7 +101,14 @@
 import org.jenkinsci.plugins.workflow.flow.FlowCopier;
 import org.jenkinsci.plugins.workflow.multibranch.WorkflowMultiBranchProject;
 import org.jenkinsci.plugins.workflow.multibranch.WorkflowMultiBranchProjectTest;
+import org.jenkinsci.plugins.workflow.steps.Step;
+import org.jenkinsci.plugins.workflow.steps.StepContext;
+import org.jenkinsci.plugins.workflow.steps.StepDescriptor;
+import org.jenkinsci.plugins.workflow.steps.StepExecution;
+import org.jenkinsci.plugins.workflow.steps.StepExecutions;
 import org.jvnet.hudson.test.MockAuthorizationStrategy;
+import org.jvnet.hudson.test.TestExtension;
+import org.kohsuke.stapler.DataBoundConstructor;
 
 public class JCloudsArtifactManagerTest extends S3AbstractTest {
 
@@ -306,6 +321,26 @@ public void contentType() throws Exception {
         assertThat(response.getContentType(), equalTo("application/json"));
     }
 
+    @Test
+    public void archiveWithDistinctArchiveAndWorkspacePaths() throws Exception {
+        String text = "some regular text";
+        ArtifactManagerConfiguration.get().getArtifactManagerFactories().add(getArtifactManagerFactory(null, null));
+
+        j.createSlave("remote", null, null);
+
+        WorkflowJob p = j.createProject(WorkflowJob.class, "p");
+        p.setDefinition(new CpsFlowDefinition(
+                "node('remote') {\n" +
+                "  writeFile file: 'f.txt', text: '" + text + "'\n" +
+                "  archiveWithCustomPath(archivePath: 'what/an/interesting/path/to/f.txt', workspacePath: 'f.txt')\n" +
+                "}", true));
+        j.buildAndAssertSuccess(p);
+
+        WebResponse response = j.createWebClient().goTo("job/p/1/artifact/what/an/interesting/path/to/f.txt", null).getWebResponse();
+        assertThat(response.getContentAsString(), equalTo(text));
+        assertThat(response.getContentType(), equalTo("text/plain"));
+    }
+
     //@Test
     public void archiveSingleLargeFile() throws Exception {
         ArtifactManagerConfiguration.get().getArtifactManagerFactories().add(getArtifactManagerFactory(null, null));
@@ -339,4 +374,36 @@ public boolean perform(AbstractBuild<?, ?> build, Launcher launcher, BuildListen
         }
     }
 
+    public static class ArchiveArtifactWithCustomPathStep extends Step implements Serializable {
+        private static final long serialVersionUID = 1L;
+        private final String archivePath;
+        private final String workspacePath;
+        @DataBoundConstructor
+        public ArchiveArtifactWithCustomPathStep(String archivePath, String workspacePath) {
+            this.archivePath = archivePath;
+            this.workspacePath = workspacePath;
+        }
+        @Override
+        public StepExecution start(StepContext context) throws Exception {
+            return StepExecutions.synchronousNonBlocking(context, context2 -> {
+                context.get(Run.class).pickArtifactManager().archive(
+                        context.get(FilePath.class),
+                        context.get(Launcher.class),
+                        new BuildListenerAdapter(context.get(TaskListener.class)),
+                        Collections.singletonMap(archivePath, workspacePath));
+                return null;
+            });
+        }
+        @TestExtension("archiveWithDistinctArchiveAndWorkspacePaths")
+        public static class DescriptorImpl extends StepDescriptor {
+            @Override
+            public String getFunctionName() {
+                return "archiveWithCustomPath";
+            }
+            @Override
+            public Set<? extends Class<?>> getRequiredContext() {
+                return Set.of(FilePath.class, Launcher.class, TaskListener.class);
+            }
+        }
+    }
 }