diff --git a/services-camel/src/main/java/edu/unc/lib/dl/services/camel/longleaf/DeregisterLongleafProcessor.java b/services-camel/src/main/java/edu/unc/lib/dl/services/camel/longleaf/DeregisterLongleafProcessor.java
index ede2e7a38c..98fcf0aec6 100644
--- a/services-camel/src/main/java/edu/unc/lib/dl/services/camel/longleaf/DeregisterLongleafProcessor.java
+++ b/services-camel/src/main/java/edu/unc/lib/dl/services/camel/longleaf/DeregisterLongleafProcessor.java
@@ -16,6 +16,7 @@
 package edu.unc.lib.dl.services.camel.longleaf;
 
 import java.net.URI;
+import java.nio.file.Path;
 import java.nio.file.Paths;
 import java.util.List;
 import java.util.stream.Collectors;
@@ -28,6 +29,7 @@
 import edu.unc.lib.dl.fedora.ServiceException;
 import edu.unc.lib.dl.metrics.HistogramFactory;
 import edu.unc.lib.dl.metrics.TimerFactory;
+import edu.unc.lib.dl.persist.services.transfer.FileSystemTransferHelpers;
 import io.dropwizard.metrics5.Histogram;
 import io.dropwizard.metrics5.Timer;
 
@@ -62,16 +64,23 @@ public void process(Exchange exchange) throws Exception {
 
         String deregList = messages.stream().map(m -> {
             URI uri = URI.create(m);
+            Path filePath;
             if ("file".equals(uri.getScheme())) {
-                return Paths.get(uri).toString();
+                filePath = Paths.get(uri);
             } else if (uri.getScheme() == null && m.startsWith("/")) {
                 // No scheme, assume it is a file path
-                return Paths.get(m).normalize().toString();
+                filePath = Paths.get(m);
             } else {
                 log.warn("Ignoring invalid content URI during deregistration: {}", m);
                 return null;
             }
-        }).filter(m -> m !=null).collect(Collectors.joining("\n"));
+            // Translate the content URI into its base logical path
+            return FileSystemTransferHelpers.getBaseBinaryPath(filePath.normalize());
+        }).filter(m -> m != null).collect(Collectors.joining("\n"));
+        // No valid content URIs to deregister
+        if (deregList.length() == 0) {
+            return;
+        }
 
         try (Timer.Context context = timer.time()) {
             ExecuteResult result = executeCommand("deregister -l @-", deregList);
diff --git a/services-camel/src/test/java/edu/unc/lib/dl/services/camel/longleaf/AbstractLongleafRouteTest.java b/services-camel/src/test/java/edu/unc/lib/dl/services/camel/longleaf/AbstractLongleafRouteTest.java
index 5d4b717b02..e6ac3e59c7 100644
--- a/services-camel/src/test/java/edu/unc/lib/dl/services/camel/longleaf/AbstractLongleafRouteTest.java
+++ b/services-camel/src/test/java/edu/unc/lib/dl/services/camel/longleaf/AbstractLongleafRouteTest.java
@@ -20,11 +20,14 @@
 import static org.slf4j.LoggerFactory.getLogger;
 
 import java.net.URI;
+import java.nio.file.Path;
 import java.nio.file.Paths;
 import java.util.List;
 
 import org.slf4j.Logger;
 
+import edu.unc.lib.dl.persist.services.transfer.FileSystemTransferHelpers;
+
 /**
  * @author bbpennel
  */
@@ -61,9 +64,15 @@ protected void assertSubmittedPaths(long timeout, String... contentUris) throws
     protected void assertSubmittedPaths(String... contentUris) {
         for (String contentUri : contentUris) {
             URI uri = URI.create(contentUri);
-            String contentPath = uri.getScheme() == null ? contentUri : Paths.get(uri).toString();
+            Path contentPath;
+            if (uri.getScheme() == null) {
+                contentPath = Paths.get(contentUri);
+            } else {
+                contentPath = Paths.get(uri);
+            }
+            String basePath = FileSystemTransferHelpers.getBaseBinaryPath(contentPath);
             assertTrue("Expected content uri to be submitted: " + contentPath,
-                    output.stream().anyMatch(line -> line.contains(contentPath)));
+                    output.stream().anyMatch(line -> line.contains(basePath)));
         }
     }
 
diff --git a/services-camel/src/test/java/edu/unc/lib/dl/services/camel/longleaf/DeregisterLongleafRouteTest.java b/services-camel/src/test/java/edu/unc/lib/dl/services/camel/longleaf/DeregisterLongleafRouteTest.java
index 6ed01047b9..d2693ac1e8 100644
--- a/services-camel/src/test/java/edu/unc/lib/dl/services/camel/longleaf/DeregisterLongleafRouteTest.java
+++ b/services-camel/src/test/java/edu/unc/lib/dl/services/camel/longleaf/DeregisterLongleafRouteTest.java
@@ -231,7 +231,7 @@ public void deregisterCommandErrorSuccessExit() throws Exception {
     }
 
     private String generateContentUri() {
-        return "file:///path/to/file/" + UUID.randomUUID().toString();
+        return "file:///path/to/file/" + UUID.randomUUID().toString() + "." + System.nanoTime();
     }
 
     private String[] generateContentUris(int num) {