diff --git a/api/src/main/java/org/apache/iceberg/types/Comparators.java b/api/src/main/java/org/apache/iceberg/types/Comparators.java
index bfbffc64b673..6d968d2055e2 100644
--- a/api/src/main/java/org/apache/iceberg/types/Comparators.java
+++ b/api/src/main/java/org/apache/iceberg/types/Comparators.java
@@ -22,6 +22,7 @@
 import java.util.Comparator;
 import java.util.List;
 import java.util.function.IntFunction;
+import org.apache.iceberg.ContentFile;
 import org.apache.iceberg.StructLike;
 import org.apache.iceberg.relocated.com.google.common.collect.ImmutableMap;
 import org.apache.iceberg.util.UnicodeUtil;
@@ -179,6 +180,10 @@ public static Comparator<CharSequence> filePath() {
     return FilePathComparator.INSTANCE;
   }
 
+  public static Comparator<ContentFile<?>> contentFile() {
+    return ContentFileComparator.INSTANCE;
+  }
+
   private static class NullsFirst<T> implements Comparator<T> {
     private static final NullsFirst<?> INSTANCE = new NullsFirst<>();
 
@@ -394,4 +399,15 @@ public int compare(CharSequence s1, CharSequence s2) {
       return 0;
     }
   }
+
+  private static class ContentFileComparator implements Comparator<ContentFile<?>> {
+    private static final ContentFileComparator INSTANCE = new ContentFileComparator();
+
+    private ContentFileComparator() {}
+
+    @Override
+    public int compare(ContentFile<?> s1, ContentFile<?> s2) {
+      return CharSeqComparator.INSTANCE.compare(s1.path(), s2.path());
+    }
+  }
 }
diff --git a/core/src/main/java/org/apache/iceberg/BaseOverwriteFiles.java b/core/src/main/java/org/apache/iceberg/BaseOverwriteFiles.java
index d929bc068ec2..18b8a177eb66 100644
--- a/core/src/main/java/org/apache/iceberg/BaseOverwriteFiles.java
+++ b/core/src/main/java/org/apache/iceberg/BaseOverwriteFiles.java
@@ -27,10 +27,11 @@
 import org.apache.iceberg.expressions.StrictMetricsEvaluator;
 import org.apache.iceberg.relocated.com.google.common.base.Preconditions;
 import org.apache.iceberg.relocated.com.google.common.collect.Sets;
+import org.apache.iceberg.types.Comparators;
 
 public class BaseOverwriteFiles extends MergingSnapshotProducer<OverwriteFiles>
     implements OverwriteFiles {
-  private final Set<DataFile> deletedDataFiles = Sets.newHashSet();
+  private final Set<DataFile> deletedDataFiles = Sets.newTreeSet(Comparators.contentFile());
   private boolean validateAddedFilesMatchOverwriteFilter = false;
   private Long startingSnapshotId = null;
   private Expression conflictDetectionFilter = null;
diff --git a/core/src/main/java/org/apache/iceberg/BaseRewriteFiles.java b/core/src/main/java/org/apache/iceberg/BaseRewriteFiles.java
index d231536d0642..510295e91271 100644
--- a/core/src/main/java/org/apache/iceberg/BaseRewriteFiles.java
+++ b/core/src/main/java/org/apache/iceberg/BaseRewriteFiles.java
@@ -22,9 +22,10 @@
 import org.apache.iceberg.relocated.com.google.common.base.Preconditions;
 import org.apache.iceberg.relocated.com.google.common.collect.ImmutableSet;
 import org.apache.iceberg.relocated.com.google.common.collect.Sets;
+import org.apache.iceberg.types.Comparators;
 
 class BaseRewriteFiles extends MergingSnapshotProducer<RewriteFiles> implements RewriteFiles {
-  private final Set<DataFile> replacedDataFiles = Sets.newHashSet();
+  private final Set<DataFile> replacedDataFiles = Sets.newTreeSet(Comparators.contentFile());
   private Long startingSnapshotId = null;
 
   BaseRewriteFiles(String tableName, TableOperations ops) {
diff --git a/core/src/main/java/org/apache/iceberg/FastAppend.java b/core/src/main/java/org/apache/iceberg/FastAppend.java
index 1bae2e2fc5a0..616e009439da 100644
--- a/core/src/main/java/org/apache/iceberg/FastAppend.java
+++ b/core/src/main/java/org/apache/iceberg/FastAppend.java
@@ -30,7 +30,8 @@
 import org.apache.iceberg.relocated.com.google.common.base.Preconditions;
 import org.apache.iceberg.relocated.com.google.common.collect.Iterables;
 import org.apache.iceberg.relocated.com.google.common.collect.Lists;
-import org.apache.iceberg.util.CharSequenceSet;
+import org.apache.iceberg.relocated.com.google.common.collect.Sets;
+import org.apache.iceberg.types.Comparators;
 
 /**
  * {@link AppendFiles Append} implementation that adds a new manifest file for the write.
@@ -44,7 +45,7 @@ class FastAppend extends SnapshotProducer<AppendFiles> implements AppendFiles {
   private final PartitionSpec spec;
   private final SnapshotSummary.Builder summaryBuilder = SnapshotSummary.builder();
   private final List<DataFile> newFiles = Lists.newArrayList();
-  private final CharSequenceSet newFilePaths = CharSequenceSet.empty();
+  private final Set<DataFile> newFileSet = Sets.newTreeSet(Comparators.contentFile());
   private final List<ManifestFile> appendManifests = Lists.newArrayList();
   private final List<ManifestFile> rewrittenAppendManifests = Lists.newArrayList();
   private List<ManifestFile> newManifests = null;
@@ -86,7 +87,7 @@ protected Map<String, String> summary() {
   @Override
   public FastAppend appendFile(DataFile file) {
     Preconditions.checkNotNull(file, "Invalid data file: null");
-    if (newFilePaths.add(file.path())) {
+    if (newFileSet.add(file)) {
       this.hasNewFiles = true;
       newFiles.add(file);
       summaryBuilder.addedFile(spec, file);
diff --git a/core/src/main/java/org/apache/iceberg/MergingSnapshotProducer.java b/core/src/main/java/org/apache/iceberg/MergingSnapshotProducer.java
index 6a4da2abc9b6..ffeaa221522d 100644
--- a/core/src/main/java/org/apache/iceberg/MergingSnapshotProducer.java
+++ b/core/src/main/java/org/apache/iceberg/MergingSnapshotProducer.java
@@ -49,6 +49,7 @@
 import org.apache.iceberg.relocated.com.google.common.collect.Lists;
 import org.apache.iceberg.relocated.com.google.common.collect.Maps;
 import org.apache.iceberg.relocated.com.google.common.collect.Sets;
+import org.apache.iceberg.types.Comparators;
 import org.apache.iceberg.util.CharSequenceSet;
 import org.apache.iceberg.util.Pair;
 import org.apache.iceberg.util.PartitionSet;
@@ -81,8 +82,8 @@ abstract class MergingSnapshotProducer<ThisT> extends SnapshotProducer<ThisT> {
 
   // update data
   private final Map<PartitionSpec, List<DataFile>> newDataFilesBySpec = Maps.newHashMap();
-  private final CharSequenceSet newDataFilePaths = CharSequenceSet.empty();
-  private final CharSequenceSet newDeleteFilePaths = CharSequenceSet.empty();
+  private final Set<DataFile> newDataFiles = Sets.newTreeSet(Comparators.contentFile());
+  private final Set<DeleteFile> newDeleteFiles = Sets.newTreeSet(Comparators.contentFile());
   private Long newDataFilesDataSequenceNumber;
   private final Map<Integer, List<DeleteFileHolder>> newDeleteFilesBySpec = Maps.newHashMap();
   private final List<ManifestFile> appendManifests = Lists.newArrayList();
@@ -234,7 +235,7 @@ protected boolean addsDeleteFiles() {
   /** Add a data file to the new snapshot. */
   protected void add(DataFile file) {
     Preconditions.checkNotNull(file, "Invalid data file: null");
-    if (newDataFilePaths.add(file.path())) {
+    if (newDataFiles.add(file)) {
       PartitionSpec fileSpec = ops.current().spec(file.specId());
       Preconditions.checkArgument(
           fileSpec != null,
@@ -268,7 +269,7 @@ private void add(DeleteFileHolder fileHolder) {
     List<DeleteFileHolder> deleteFiles =
         newDeleteFilesBySpec.computeIfAbsent(specId, s -> Lists.newArrayList());
 
-    if (newDeleteFilePaths.add(fileHolder.deleteFile().path())) {
+    if (newDeleteFiles.add(fileHolder.deleteFile())) {
       deleteFiles.add(fileHolder);
       addedFilesSummary.addedFile(fileSpec, fileHolder.deleteFile());
       hasNewDeleteFiles = true;
diff --git a/core/src/main/java/org/apache/iceberg/actions/RewriteDataFilesCommitManager.java b/core/src/main/java/org/apache/iceberg/actions/RewriteDataFilesCommitManager.java
index 45b4bcf0a4d9..435a5e4b118e 100644
--- a/core/src/main/java/org/apache/iceberg/actions/RewriteDataFilesCommitManager.java
+++ b/core/src/main/java/org/apache/iceberg/actions/RewriteDataFilesCommitManager.java
@@ -28,6 +28,7 @@
 import org.apache.iceberg.relocated.com.google.common.base.Preconditions;
 import org.apache.iceberg.relocated.com.google.common.collect.ImmutableMap;
 import org.apache.iceberg.relocated.com.google.common.collect.Sets;
+import org.apache.iceberg.types.Comparators;
 import org.apache.iceberg.util.Tasks;
 import org.slf4j.Logger;
 import org.slf4j.LoggerFactory;
@@ -73,8 +74,8 @@ public RewriteDataFilesCommitManager(
    * @param fileGroups fileSets to commit
    */
   public void commitFileGroups(Set<RewriteFileGroup> fileGroups) {
-    Set<DataFile> rewrittenDataFiles = Sets.newHashSet();
-    Set<DataFile> addedDataFiles = Sets.newHashSet();
+    Set<DataFile> rewrittenDataFiles = Sets.newTreeSet(Comparators.contentFile());
+    Set<DataFile> addedDataFiles = Sets.newTreeSet(Comparators.contentFile());
     for (RewriteFileGroup group : fileGroups) {
       rewrittenDataFiles.addAll(group.rewrittenFiles());
       addedDataFiles.addAll(group.addedFiles());
diff --git a/core/src/main/java/org/apache/iceberg/actions/RewriteFileGroup.java b/core/src/main/java/org/apache/iceberg/actions/RewriteFileGroup.java
index dd1358f2ed40..63bb8b26352e 100644
--- a/core/src/main/java/org/apache/iceberg/actions/RewriteFileGroup.java
+++ b/core/src/main/java/org/apache/iceberg/actions/RewriteFileGroup.java
@@ -18,7 +18,6 @@
  */
 package org.apache.iceberg.actions;
 
-import java.util.Collections;
 import java.util.Comparator;
 import java.util.List;
 import java.util.Set;
@@ -29,6 +28,8 @@
 import org.apache.iceberg.actions.RewriteDataFiles.FileGroupInfo;
 import org.apache.iceberg.relocated.com.google.common.base.MoreObjects;
 import org.apache.iceberg.relocated.com.google.common.base.Preconditions;
+import org.apache.iceberg.relocated.com.google.common.collect.Sets;
+import org.apache.iceberg.types.Comparators;
 
 /**
  * Container class representing a set of files to be rewritten by a RewriteAction and the new files
@@ -38,7 +39,7 @@ public class RewriteFileGroup {
   private final FileGroupInfo info;
   private final List<FileScanTask> fileScanTasks;
 
-  private Set<DataFile> addedFiles = Collections.emptySet();
+  private Set<DataFile> addedFiles = Sets.newTreeSet(Comparators.contentFile());
 
   public RewriteFileGroup(FileGroupInfo info, List<FileScanTask> fileScanTasks) {
     this.info = info;
diff --git a/core/src/main/java/org/apache/iceberg/actions/RewritePositionDeletesGroup.java b/core/src/main/java/org/apache/iceberg/actions/RewritePositionDeletesGroup.java
index 2be7145bcd34..8a24eafb412f 100644
--- a/core/src/main/java/org/apache/iceberg/actions/RewritePositionDeletesGroup.java
+++ b/core/src/main/java/org/apache/iceberg/actions/RewritePositionDeletesGroup.java
@@ -18,7 +18,6 @@
  */
 package org.apache.iceberg.actions;
 
-import java.util.Collections;
 import java.util.Comparator;
 import java.util.List;
 import java.util.Set;
@@ -30,6 +29,8 @@
 import org.apache.iceberg.actions.RewritePositionDeleteFiles.FileGroupRewriteResult;
 import org.apache.iceberg.relocated.com.google.common.base.MoreObjects;
 import org.apache.iceberg.relocated.com.google.common.base.Preconditions;
+import org.apache.iceberg.relocated.com.google.common.collect.Sets;
+import org.apache.iceberg.types.Comparators;
 
 /**
  * Container class representing a set of position delete files to be rewritten by a {@link
@@ -40,7 +41,7 @@ public class RewritePositionDeletesGroup {
   private final List<PositionDeletesScanTask> tasks;
   private final long maxRewrittenDataSequenceNumber;
 
-  private Set<DeleteFile> addedDeleteFiles = Collections.emptySet();
+  private Set<DeleteFile> addedDeleteFiles = Sets.newTreeSet(Comparators.contentFile());
 
   public RewritePositionDeletesGroup(FileGroupInfo info, List<PositionDeletesScanTask> tasks) {
     Preconditions.checkArgument(!tasks.isEmpty(), "Tasks must not be empty");
@@ -67,7 +68,9 @@ public long maxRewrittenDataSequenceNumber() {
   }
 
   public Set<DeleteFile> rewrittenDeleteFiles() {
-    return tasks().stream().map(PositionDeletesScanTask::file).collect(Collectors.toSet());
+    return tasks().stream()
+        .map(PositionDeletesScanTask::file)
+        .collect(Collectors.toCollection(() -> Sets.newTreeSet(Comparators.contentFile())));
   }
 
   public Set<DeleteFile> addedDeleteFiles() {
diff --git a/spark/v3.5/spark/src/test/java/org/apache/iceberg/spark/data/TestHelpers.java b/spark/v3.5/spark/src/test/java/org/apache/iceberg/spark/data/TestHelpers.java
index c73ef630ac48..6fdde47905bd 100644
--- a/spark/v3.5/spark/src/test/java/org/apache/iceberg/spark/data/TestHelpers.java
+++ b/spark/v3.5/spark/src/test/java/org/apache/iceberg/spark/data/TestHelpers.java
@@ -57,6 +57,7 @@
 import org.apache.iceberg.relocated.com.google.common.collect.Sets;
 import org.apache.iceberg.relocated.com.google.common.collect.Streams;
 import org.apache.iceberg.spark.SparkSchemaUtil;
+import org.apache.iceberg.types.Comparators;
 import org.apache.iceberg.types.Type;
 import org.apache.iceberg.types.Types;
 import org.apache.orc.storage.serde2.io.DateWritable;
@@ -787,7 +788,7 @@ public static List<DataFile> dataFiles(Table table, String branch) {
   }
 
   public static Set<DeleteFile> deleteFiles(Table table) {
-    Set<DeleteFile> deleteFiles = Sets.newHashSet();
+    Set<DeleteFile> deleteFiles = Sets.newTreeSet(Comparators.contentFile());
 
     for (FileScanTask task : table.newScan().planFiles()) {
       deleteFiles.addAll(task.deletes());