diff --git a/core/src/main/java/org/apache/iceberg/BaseUpdatePartitionSpec.java b/core/src/main/java/org/apache/iceberg/BaseUpdatePartitionSpec.java
index e1fe84be1dc3..80f8188002d5 100644
--- a/core/src/main/java/org/apache/iceberg/BaseUpdatePartitionSpec.java
+++ b/core/src/main/java/org/apache/iceberg/BaseUpdatePartitionSpec.java
@@ -142,13 +142,26 @@ public BaseUpdatePartitionSpec addField(String name, Term term) {
 
     PartitionField newField = new PartitionField(
         sourceTransform.first(), assignFieldId(), name, sourceTransform.second());
-    checkForRedundantAddedPartitions(newField);
+    if (newField.name() == null) {
+      String partitionName = PartitionSpecVisitor.visit(schema, newField, PartitionNameGenerator.INSTANCE);
+      newField = new PartitionField(newField.sourceId(), newField.fieldId(), partitionName, newField.transform());
+    }
 
+    checkForRedundantAddedPartitions(newField);
     transformToAddedField.put(validationKey, newField);
-    if (name != null) {
-      nameToAddedField.put(name, newField);
+
+    PartitionField existingField = nameToField.get(newField.name());
+    if (existingField != null) {
+      if (isVoidTransform(existingField)) {
+        // rename the old deleted field that is being replaced by the new field
+        renameField(existingField.name(), existingField.name() + "_" + existingField.fieldId());
+      } else {
+        throw new IllegalArgumentException(String.format("Cannot add duplicate partition field name: %s", name));
+      }
     }
 
+    nameToAddedField.put(newField.name(), newField);
+
     adds.add(newField);
 
     return this;
@@ -192,6 +205,12 @@ public BaseUpdatePartitionSpec removeField(Term term) {
 
   @Override
   public BaseUpdatePartitionSpec renameField(String name, String newName) {
+    PartitionField existingField = nameToField.get(newName);
+    if (existingField != null && isVoidTransform(existingField)) {
+      // rename the old deleted field that is being replaced by the new field
+      renameField(existingField.name(), existingField.name() + "_" + existingField.fieldId());
+    }
+
     PartitionField added = nameToAddedField.get(name);
     Preconditions.checkArgument(added == null,
         "Cannot rename newly added partition field: %s", name);
@@ -228,14 +247,7 @@ public PartitionSpec apply() {
     }
 
     for (PartitionField newField : adds) {
-      String partitionName;
-      if (newField.name() != null) {
-        partitionName = newField.name();
-      } else {
-        partitionName = PartitionSpecVisitor.visit(schema, newField, PartitionNameGenerator.INSTANCE);
-      }
-
-      builder.add(newField.sourceId(), newField.fieldId(), partitionName, newField.transform());
+      builder.add(newField.sourceId(), newField.fieldId(), newField.name(), newField.transform());
     }
 
     return builder.build();
@@ -287,13 +299,13 @@ private static Map<String, PartitionField> indexSpecByName(PartitionSpec spec) {
   }
 
   private static Map<Pair<Integer, String>, PartitionField> indexSpecByTransform(PartitionSpec spec) {
-    ImmutableMap.Builder<Pair<Integer, String>, PartitionField> builder = ImmutableMap.builder();
+    Map<Pair<Integer, String>, PartitionField> indexSpecs = Maps.newHashMap();
     List<PartitionField> fields = spec.fields();
     for (PartitionField field : fields) {
-      builder.put(Pair.of(field.sourceId(), field.transform().toString()), field);
+      indexSpecs.put(Pair.of(field.sourceId(), field.transform().toString()), field);
     }
 
-    return builder.build();
+    return indexSpecs;
   }
 
   private boolean isTimeTransform(PartitionField field) {
@@ -352,6 +364,62 @@ public Boolean unknown(int fieldId, String sourceName, int sourceId, String tran
     }
   }
 
+  private boolean isVoidTransform(PartitionField field) {
+    return PartitionSpecVisitor.visit(schema, field, IsVoidTransform.INSTANCE);
+  }
+
+  private static class IsVoidTransform implements PartitionSpecVisitor<Boolean> {
+    private static final IsVoidTransform INSTANCE = new IsVoidTransform();
+
+    private IsVoidTransform() {
+    }
+
+    @Override
+    public Boolean identity(int fieldId, String sourceName, int sourceId) {
+      return false;
+    }
+
+    @Override
+    public Boolean bucket(int fieldId, String sourceName, int sourceId, int numBuckets) {
+      return false;
+    }
+
+    @Override
+    public Boolean truncate(int fieldId, String sourceName, int sourceId, int width) {
+      return false;
+    }
+
+    @Override
+    public Boolean year(int fieldId, String sourceName, int sourceId) {
+      return false;
+    }
+
+    @Override
+    public Boolean month(int fieldId, String sourceName, int sourceId) {
+      return false;
+    }
+
+    @Override
+    public Boolean day(int fieldId, String sourceName, int sourceId) {
+      return false;
+    }
+
+    @Override
+    public Boolean hour(int fieldId, String sourceName, int sourceId) {
+      return false;
+    }
+
+    @Override
+    public Boolean alwaysNull(int fieldId, String sourceName, int sourceId) {
+      return true;
+    }
+
+    @Override
+    public Boolean unknown(int fieldId, String sourceName, int sourceId, String transform) {
+      return false;
+    }
+  }
+
   private static class PartitionNameGenerator implements PartitionSpecVisitor<String> {
     private static final PartitionNameGenerator INSTANCE = new PartitionNameGenerator();
 
diff --git a/core/src/test/java/org/apache/iceberg/TestUpdatePartitionSpec.java b/core/src/test/java/org/apache/iceberg/TestUpdatePartitionSpec.java
index 1c0fc76534a2..c65dd2e3343f 100644
--- a/core/src/test/java/org/apache/iceberg/TestUpdatePartitionSpec.java
+++ b/core/src/test/java/org/apache/iceberg/TestUpdatePartitionSpec.java
@@ -569,6 +569,51 @@ public void testRenameAndDelete() {
             .renameField("shard", "id_bucket"));
   }
 
+  @Test
+  public void testRemoveAndAddMultiTimes() {
+    PartitionSpec addFirstTime = new BaseUpdatePartitionSpec(formatVersion, UNPARTITIONED)
+            .addField("ts_date", day("ts"))
+            .apply();
+    PartitionSpec removeFirstTime = new BaseUpdatePartitionSpec(formatVersion, addFirstTime)
+            .removeField(day("ts"))
+            .apply();
+    PartitionSpec addSecondTime = new BaseUpdatePartitionSpec(formatVersion, removeFirstTime)
+            .addField("ts_date", day("ts"))
+            .apply();
+    PartitionSpec removeSecondTime = new BaseUpdatePartitionSpec(formatVersion, addSecondTime)
+            .removeField(day("ts"))
+            .apply();
+    PartitionSpec addThirdTime = new BaseUpdatePartitionSpec(formatVersion, removeSecondTime)
+            .addField(month("ts"))
+            .apply();
+    PartitionSpec updated = new BaseUpdatePartitionSpec(formatVersion, addThirdTime)
+            .renameField("ts_month", "ts_date")
+            .apply();
+
+    if (formatVersion == 1) {
+      Assert.assertEquals("Should match expected spec field size", 3, updated.fields().size());
+
+      Assert.assertTrue("Should match expected field name",
+              updated.fields().get(0).name().matches("^ts_date(?:_\\d+)+$"));
+      Assert.assertTrue("Should match expected field name",
+              updated.fields().get(1).name().matches("^ts_date_(?:\\d+)+$"));
+      Assert.assertEquals("Should match expected field name", "ts_date", updated.fields().get(2).name());
+
+      Assert.assertEquals("Should match expected field transform", "void",
+              updated.fields().get(0).transform().toString());
+      Assert.assertEquals("Should match expected field transform", "void",
+              updated.fields().get(1).transform().toString());
+      Assert.assertEquals("Should match expected field transform", "month",
+              updated.fields().get(2).transform().toString());
+    }
+
+    PartitionSpec v2Expected = PartitionSpec.builderFor(SCHEMA)
+            .month("ts", "ts_date")
+            .build();
+
+    V2Assert.assertEquals("Should match expected spec", v2Expected, updated);
+  }
+
   private static int id(String name) {
     return SCHEMA.findField(name).fieldId();
   }