diff --git a/core/src/main/java/org/apache/iceberg/BaseRewriteFiles.java b/core/src/main/java/org/apache/iceberg/BaseRewriteFiles.java
index b25681de4238..60961ca72f7f 100644
--- a/core/src/main/java/org/apache/iceberg/BaseRewriteFiles.java
+++ b/core/src/main/java/org/apache/iceberg/BaseRewriteFiles.java
@@ -152,5 +152,12 @@ private void validateReplacedAndAddedFiles() {
     Preconditions.checkArgument(
         deletesDeleteFiles() || !addsDeleteFiles(),
         "Delete files to add must be empty because there's no delete file to be rewritten");
+
+    for (DataFile added : addedDataFiles()) {
+      Preconditions.checkArgument(
+          !replacedDataFiles.contains(added),
+          "Cannot add and delete the same file in the same rewrite: %s",
+          added.location());
+    }
   }
 }
diff --git a/core/src/test/java/org/apache/iceberg/TestRewriteFiles.java b/core/src/test/java/org/apache/iceberg/TestRewriteFiles.java
index 72a3c89b74d5..5eba212a9bdd 100644
--- a/core/src/test/java/org/apache/iceberg/TestRewriteFiles.java
+++ b/core/src/test/java/org/apache/iceberg/TestRewriteFiles.java
@@ -172,6 +172,22 @@ public void testDeleteOnly() {
         .hasMessage("Files to delete cannot be empty");
   }
 
+  @TestTemplate
+  public void addingAndDeletingSameFileDisallowed() {
+    assertThat(listManifestFiles()).isEmpty();
+
+    commit(table, table.newAppend().appendFile(FILE_A).appendFile(FILE_B), branch);
+
+    assertThatThrownBy(
+            () ->
+                apply(
+                    table.newRewrite().rewriteFiles(Sets.newSet(FILE_A), Sets.newSet(FILE_A)),
+                    branch))
+        .isInstanceOf(IllegalArgumentException.class)
+        .hasMessage(
+            "Cannot add and delete the same file in the same rewrite: " + FILE_A.location());
+  }
+
   @TestTemplate
   public void testDeleteWithDuplicateEntriesInManifest() {
     assertThat(listManifestFiles()).isEmpty();
diff --git a/flink/v1.20/flink/src/test/java/org/apache/iceberg/flink/maintenance/operator/TestMonitorSource.java b/flink/v1.20/flink/src/test/java/org/apache/iceberg/flink/maintenance/operator/TestMonitorSource.java
index 34bb14336511..56c89874b111 100644
--- a/flink/v1.20/flink/src/test/java/org/apache/iceberg/flink/maintenance/operator/TestMonitorSource.java
+++ b/flink/v1.20/flink/src/test/java/org/apache/iceberg/flink/maintenance/operator/TestMonitorSource.java
@@ -39,6 +39,7 @@
 import org.apache.iceberg.DataFile;
 import org.apache.iceberg.DeleteFile;
 import org.apache.iceberg.FileFormat;
+import org.apache.iceberg.FileGenerationUtil;
 import org.apache.iceberg.RewriteFiles;
 import org.apache.iceberg.SnapshotChanges;
 import org.apache.iceberg.Table;
@@ -310,10 +311,11 @@ void testSkipReplace() throws IOException {
     // Create a DataOperations.REPLACE snapshot
     DataFile dataFile =
         SnapshotChanges.builderFor(table).build().addedDataFiles().iterator().next();
+    // Replace the file with a new file to produce a REPLACE snapshot
+    DataFile replacement = FileGenerationUtil.generateDataFile(table, null);
     RewriteFiles rewrite = tableLoader.loadTable().newRewrite();
-    // Replace the file with itself for testing purposes
     rewrite.deleteFile(dataFile);
-    rewrite.addFile(dataFile);
+    rewrite.addFile(replacement);
     rewrite.commit();
 
     // Check that the rewrite is ignored
diff --git a/flink/v2.0/flink/src/test/java/org/apache/iceberg/flink/maintenance/operator/TestMonitorSource.java b/flink/v2.0/flink/src/test/java/org/apache/iceberg/flink/maintenance/operator/TestMonitorSource.java
index 3dca6c421c76..af73178ed56d 100644
--- a/flink/v2.0/flink/src/test/java/org/apache/iceberg/flink/maintenance/operator/TestMonitorSource.java
+++ b/flink/v2.0/flink/src/test/java/org/apache/iceberg/flink/maintenance/operator/TestMonitorSource.java
@@ -45,6 +45,7 @@
 import org.apache.iceberg.DataFile;
 import org.apache.iceberg.DeleteFile;
 import org.apache.iceberg.FileFormat;
+import org.apache.iceberg.FileGenerationUtil;
 import org.apache.iceberg.RewriteFiles;
 import org.apache.iceberg.SnapshotChanges;
 import org.apache.iceberg.Table;
@@ -318,10 +319,11 @@ void testSkipReplace() throws IOException {
     // Create a DataOperations.REPLACE snapshot
     DataFile dataFile =
         SnapshotChanges.builderFor(table).build().addedDataFiles().iterator().next();
+    // Replace the file with a new file to produce a REPLACE snapshot
+    DataFile replacement = FileGenerationUtil.generateDataFile(table, null);
     RewriteFiles rewrite = tableLoader.loadTable().newRewrite();
-    // Replace the file with itself for testing purposes
     rewrite.deleteFile(dataFile);
-    rewrite.addFile(dataFile);
+    rewrite.addFile(replacement);
     rewrite.commit();
 
     // Check that the rewrite is ignored
diff --git a/flink/v2.1/flink/src/test/java/org/apache/iceberg/flink/maintenance/operator/TestMonitorSource.java b/flink/v2.1/flink/src/test/java/org/apache/iceberg/flink/maintenance/operator/TestMonitorSource.java
index 3dca6c421c76..af73178ed56d 100644
--- a/flink/v2.1/flink/src/test/java/org/apache/iceberg/flink/maintenance/operator/TestMonitorSource.java
+++ b/flink/v2.1/flink/src/test/java/org/apache/iceberg/flink/maintenance/operator/TestMonitorSource.java
@@ -45,6 +45,7 @@
 import org.apache.iceberg.DataFile;
 import org.apache.iceberg.DeleteFile;
 import org.apache.iceberg.FileFormat;
+import org.apache.iceberg.FileGenerationUtil;
 import org.apache.iceberg.RewriteFiles;
 import org.apache.iceberg.SnapshotChanges;
 import org.apache.iceberg.Table;
@@ -318,10 +319,11 @@ void testSkipReplace() throws IOException {
     // Create a DataOperations.REPLACE snapshot
     DataFile dataFile =
         SnapshotChanges.builderFor(table).build().addedDataFiles().iterator().next();
+    // Replace the file with a new file to produce a REPLACE snapshot
+    DataFile replacement = FileGenerationUtil.generateDataFile(table, null);
     RewriteFiles rewrite = tableLoader.loadTable().newRewrite();
-    // Replace the file with itself for testing purposes
     rewrite.deleteFile(dataFile);
-    rewrite.addFile(dataFile);
+    rewrite.addFile(replacement);
     rewrite.commit();
 
     // Check that the rewrite is ignored