diff --git a/src/main/java/com/google/devtools/build/lib/analysis/config/BuildConfiguration.java b/src/main/java/com/google/devtools/build/lib/analysis/config/BuildConfiguration.java
index 73fbc53..cbc7447 100644
--- a/src/main/java/com/google/devtools/build/lib/analysis/config/BuildConfiguration.java
+++ b/src/main/java/com/google/devtools/build/lib/analysis/config/BuildConfiguration.java
@@ -37,6 +37,7 @@
 import com.google.devtools.build.lib.analysis.BlazeDirectories;
 import com.google.devtools.build.lib.analysis.ConfiguredRuleClassProvider;
 import com.google.devtools.build.lib.analysis.actions.FileWriteAction;
+import com.google.devtools.build.lib.analysis.skylark.StarlarkConverter;
 import com.google.devtools.build.lib.buildeventstream.BuildEventId;
 import com.google.devtools.build.lib.buildeventstream.BuildEventStreamProtos;
 import com.google.devtools.build.lib.cmdline.Label;
@@ -50,6 +51,7 @@
 import com.google.devtools.build.lib.skylarkbuildapi.BuildConfigurationApi;
 import com.google.devtools.build.lib.skylarkinterface.SkylarkInterfaceUtils;
 import com.google.devtools.build.lib.skylarkinterface.SkylarkModule;
+import com.google.devtools.build.lib.syntax.SkylarkDict;
 import com.google.devtools.build.lib.util.OS;
 import com.google.devtools.build.lib.util.RegexFilter;
 import com.google.devtools.build.lib.vfs.Path;
@@ -321,15 +323,28 @@
         help = "If true, the genfiles directory is folded into the bin directory.")
     public boolean mergeGenfilesDirectory;
 
+    /**
+     * AssignmentConverter that also supports Starlarkization. For use with options that use {@link
+     * com.google.devtools.common.options.Converters.AssignmentConverter} and
+     * {@link @Option#allowMultiple}.
+     */
+    public static class StarlarkAssignmentConverter extends Converters.AssignmentConverter
+        implements StarlarkConverter<List<Map.Entry<String, String>>, Map.Entry<String, String>> {
+      @Override
+      public SkylarkDict<String, String> convertToStarlark(
+          List<Map.Entry<String, String>> entries) {
+        return SkylarkDict.copyOf(null, ImmutableMap.copyOf(entries));
+      }
+    }
+
     @Option(
-      name = "define",
-      converter = Converters.AssignmentConverter.class,
-      defaultValue = "",
-      allowMultiple = true,
-      documentationCategory = OptionDocumentationCategory.OUTPUT_PARAMETERS,
-      effectTags = {OptionEffectTag.CHANGES_INPUTS, OptionEffectTag.AFFECTS_OUTPUTS},
-      help = "Each --define option specifies an assignment for a build variable."
-    )
+        name = "define",
+        converter = StarlarkAssignmentConverter.class,
+        defaultValue = "",
+        allowMultiple = true,
+        documentationCategory = OptionDocumentationCategory.OUTPUT_PARAMETERS,
+        effectTags = {OptionEffectTag.CHANGES_INPUTS, OptionEffectTag.AFFECTS_OUTPUTS},
+        help = "Each --define option specifies an assignment for a build variable.")
     public List<Map.Entry<String, String>> commandLineBuildVariables;
 
     @Option(
diff --git a/src/main/java/com/google/devtools/build/lib/analysis/skylark/FunctionTransitionUtil.java b/src/main/java/com/google/devtools/build/lib/analysis/skylark/FunctionTransitionUtil.java
index c014b8a6..d074579 100644
--- a/src/main/java/com/google/devtools/build/lib/analysis/skylark/FunctionTransitionUtil.java
+++ b/src/main/java/com/google/devtools/build/lib/analysis/skylark/FunctionTransitionUtil.java
@@ -17,6 +17,7 @@
 import static java.nio.charset.StandardCharsets.US_ASCII;
 
 import com.google.common.base.Joiner;
+import com.google.common.base.Preconditions;
 import com.google.common.collect.ImmutableList;
 import com.google.common.collect.ImmutableMap;
 import com.google.common.collect.ImmutableSet;
@@ -34,6 +35,8 @@
 import com.google.devtools.build.lib.syntax.Runtime.NoneType;
 import com.google.devtools.build.lib.syntax.SkylarkDict;
 import com.google.devtools.build.lib.syntax.SkylarkList;
+import com.google.devtools.build.lib.syntax.SkylarkType;
+import com.google.devtools.common.options.Converter;
 import com.google.devtools.common.options.OptionDefinition;
 import com.google.devtools.common.options.OptionsParser;
 import com.google.devtools.common.options.OptionsParsingException;
@@ -153,7 +156,7 @@
    * @throws EvalException if any of the specified transition inputs do not correspond to a valid
    *     build setting
    */
-  static SkylarkDict<String, Object> buildSettings(
+  static <S, T> SkylarkDict<String, Object> buildSettings(
       BuildOptions buildOptions,
       Map<String, OptionInfo> optionInfoMap,
       StarlarkDefinedConfigTransition starlarkTransition)
@@ -178,10 +181,29 @@
           Field field = optionInfo.getDefinition().getField();
           FragmentOptions options = buildOptions.get(optionInfo.getOptionClass());
           Object optionValue = field.get(options);
-
-          dict.put(optionKey, optionValue == null ? Runtime.NONE : optionValue, null, mutability);
+          Converter<?> converter = optionInfo.getDefinition().getConverter();
+          if (converter instanceof StarlarkConverter) {
+            @SuppressWarnings("unchecked") // Type erasure
+            Object convertedValue =
+                ((StarlarkConverter<S, T>) converter).convertToStarlark((S) optionValue);
+            Preconditions.checkNotNull(convertedValue);
+            optionValue = convertedValue;
+          } else if (optionValue == null) {
+            optionValue = Runtime.NONE;
+          } else {
+            optionValue = SkylarkType.convertToSkylark(optionValue, mutability);
+            if (optionValue != null && !SkylarkType.isSkylarkAcceptable(optionValue.getClass())) {
+              throw new EvalException(
+                  starlarkTransition.getLocationForErrorReporting(),
+                  String.format(
+                      "Unable to read option '%s' -  option '%s' is Starlark incompatible.",
+                      optionKey, optionKey));
+            }
+          }
+          dict.put(optionKey, optionValue, null, mutability);
         } catch (IllegalAccessException e) {
-          // These exceptions should not happen, but if they do, throw a RuntimeException.
+          // These exceptions should not happen since all options should be public, but if they
+          // do, throw a RuntimeException.
           throw new RuntimeException(e);
         }
       }
diff --git a/src/main/java/com/google/devtools/build/lib/analysis/skylark/StarlarkConverter.java b/src/main/java/com/google/devtools/build/lib/analysis/skylark/StarlarkConverter.java
new file mode 100644
index 0000000..6798fab
--- /dev/null
+++ b/src/main/java/com/google/devtools/build/lib/analysis/skylark/StarlarkConverter.java
@@ -0,0 +1,44 @@
+// Copyright 2019 The Bazel Authors. All rights reserved.
+//
+// Licensed under the Apache License, Version 2.0 (the "License");
+// you may not use this file except in compliance with the License.
+// You may obtain a copy of the License at
+//
+//    http://www.apache.org/licenses/LICENSE-2.0
+//
+// Unless required by applicable law or agreed to in writing, software
+// distributed under the License is distributed on an "AS IS" BASIS,
+// WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+// See the License for the specific language governing permissions and
+// limitations under the License.
+
+package com.google.devtools.build.lib.analysis.skylark;
+
+import com.google.devtools.build.lib.skylarkinterface.SkylarkValue;
+import com.google.devtools.common.options.Converter;
+
+/**
+ * A converter that also knows how to turn a native object into a Starlark object
+ *
+ * <p>This interface declares/inherits two converting methods:
+ *
+ * <p>For converting from command line to Java (inherited)
+ *
+ * <p>{@code convert} String -> Object<T>
+ *
+ * <p>For converting from Java to Starlark
+ *
+ * <p>{@code convertToStarlark} Object<S> -> SkylarkValue
+ *
+ * <p>In practice, <T> and <S> will almost always be the same type. An example of an exception to
+ * this rule is for options with {@code allowMultiple = true} for which <S> is a list of <T>
+ * objects.
+ */
+// TODO(juliexxia): Add Starlark -> Java converter method to this interface.
+public interface StarlarkConverter<S, T> extends Converter<T> {
+
+  /** Convert a java object of type S into a Starlark friendly value. */
+  // TODO(bazel-team): exapnd this interface to allow "primitive" types to also be returned here.
+  // Example case of where this would be useful is for {@code enum}s.
+  SkylarkValue convertToStarlark(S input);
+}
diff --git a/src/main/java/com/google/devtools/build/lib/syntax/EvalUtils.java b/src/main/java/com/google/devtools/build/lib/syntax/EvalUtils.java
index 38e7710..d8583b4 100644
--- a/src/main/java/com/google/devtools/build/lib/syntax/EvalUtils.java
+++ b/src/main/java/com/google/devtools/build/lib/syntax/EvalUtils.java
@@ -25,7 +25,6 @@
 import com.google.devtools.build.lib.skylarkinterface.SkylarkInterfaceUtils;
 import com.google.devtools.build.lib.skylarkinterface.SkylarkModule;
 import com.google.devtools.build.lib.skylarkinterface.SkylarkValue;
-import com.google.devtools.build.lib.vfs.PathFragment;
 import java.util.Collection;
 import java.util.List;
 import java.util.Map;
@@ -147,21 +146,6 @@
         || c.equals(Boolean.class);
   }
 
-  /**
-   * Returns true if the type is acceptable to be returned to the Skylark language.
-   */
-  public static boolean isSkylarkAcceptable(Class<?> c) {
-    return SkylarkValue.class.isAssignableFrom(c) // implements SkylarkValue
-        || c.equals(String.class) // basic values
-        || c.equals(Integer.class)
-        || c.equals(Boolean.class)
-        // there is a registered Skylark ancestor class (useful e.g. when using AutoValue)
-        || SkylarkInterfaceUtils.getSkylarkModule(c) != null
-        || ImmutableMap.class.isAssignableFrom(c) // will be converted to SkylarkDict
-        || NestedSet.class.isAssignableFrom(c) // will be converted to SkylarkNestedSet
-        || PathFragment.class.isAssignableFrom(c); // other known class
-  }
-
   // TODO(bazel-team): move the following few type-related functions to SkylarkType
   /**
    * Return the Skylark-type of {@code c}
diff --git a/src/main/java/com/google/devtools/build/lib/syntax/MethodDescriptor.java b/src/main/java/com/google/devtools/build/lib/syntax/MethodDescriptor.java
index b322d23..4bf6281 100644
--- a/src/main/java/com/google/devtools/build/lib/syntax/MethodDescriptor.java
+++ b/src/main/java/com/google/devtools/build/lib/syntax/MethodDescriptor.java
@@ -148,7 +148,7 @@
       }
       // TODO(bazel-team): get rid of this, by having everyone use the Skylark data structures
       result = SkylarkType.convertToSkylark(result, method, env);
-      if (result != null && !EvalUtils.isSkylarkAcceptable(result.getClass())) {
+      if (result != null && !SkylarkType.isSkylarkAcceptable(result.getClass())) {
         throw new EvalException(
             loc,
             Printer.format(
diff --git a/src/main/java/com/google/devtools/build/lib/syntax/SkylarkType.java b/src/main/java/com/google/devtools/build/lib/syntax/SkylarkType.java
index a714782..84afa81 100644
--- a/src/main/java/com/google/devtools/build/lib/syntax/SkylarkType.java
+++ b/src/main/java/com/google/devtools/build/lib/syntax/SkylarkType.java
@@ -26,9 +26,11 @@
 import com.google.devtools.build.lib.events.Location;
 import com.google.devtools.build.lib.skyframe.serialization.autocodec.AutoCodec;
 import com.google.devtools.build.lib.skyframe.serialization.autocodec.AutoCodec.VisibleForSerialization;
+import com.google.devtools.build.lib.skylarkinterface.SkylarkInterfaceUtils;
 import com.google.devtools.build.lib.skylarkinterface.SkylarkValue;
 import com.google.devtools.build.lib.syntax.SkylarkList.MutableList;
 import com.google.devtools.build.lib.syntax.SkylarkList.Tuple;
+import com.google.devtools.build.lib.vfs.PathFragment;
 import java.io.Serializable;
 import java.lang.reflect.Method;
 import java.lang.reflect.ParameterizedType;
@@ -663,6 +665,19 @@
     return true;
   }
 
+  /** Returns true if the type is acceptable to be returned to the Skylark language. */
+  public static boolean isSkylarkAcceptable(Class<?> c) {
+    return SkylarkValue.class.isAssignableFrom(c) // implements SkylarkValue
+        || c.equals(String.class) // basic values
+        || c.equals(Integer.class)
+        || c.equals(Boolean.class)
+        // there is a registered Skylark ancestor class (useful e.g. when using AutoValue)
+        || SkylarkInterfaceUtils.getSkylarkModule(c) != null
+        || ImmutableMap.class.isAssignableFrom(c) // will be converted to SkylarkDict
+        || NestedSet.class.isAssignableFrom(c) // will be converted to SkylarkNestedSet
+        || PathFragment.class.isAssignableFrom(c); // other known class
+  }
+
   /**
    * Throws EvalException if the type of the object is not allowed to be present in Skylark.
    */
diff --git a/src/test/java/com/google/devtools/build/lib/analysis/StarlarkRuleTransitionProviderTest.java b/src/test/java/com/google/devtools/build/lib/analysis/StarlarkRuleTransitionProviderTest.java
index c56d4eb..03ef28f 100644
--- a/src/test/java/com/google/devtools/build/lib/analysis/StarlarkRuleTransitionProviderTest.java
+++ b/src/test/java/com/google/devtools/build/lib/analysis/StarlarkRuleTransitionProviderTest.java
@@ -21,6 +21,7 @@
 import com.google.devtools.build.lib.analysis.config.BuildConfiguration;
 import com.google.devtools.build.lib.analysis.config.BuildConfiguration.EmptyToNullLabelConverter;
 import com.google.devtools.build.lib.analysis.config.BuildConfiguration.Fragment;
+import com.google.devtools.build.lib.analysis.config.BuildConfiguration.Options.StarlarkAssignmentConverter;
 import com.google.devtools.build.lib.analysis.config.BuildOptions;
 import com.google.devtools.build.lib.analysis.config.ConfigurationFragmentFactory;
 import com.google.devtools.build.lib.analysis.config.FragmentOptions;
@@ -29,10 +30,11 @@
 import com.google.devtools.build.lib.analysis.util.BuildViewTestCase;
 import com.google.devtools.build.lib.cmdline.Label;
 import com.google.devtools.build.lib.testutil.TestRuleClassProvider;
-import com.google.devtools.common.options.Converters;
+import com.google.devtools.common.options.Converter;
 import com.google.devtools.common.options.Option;
 import com.google.devtools.common.options.OptionDocumentationCategory;
 import com.google.devtools.common.options.OptionEffectTag;
+import com.google.devtools.common.options.OptionsParsingException;
 import java.util.List;
 import java.util.Map;
 import org.junit.Test;
@@ -61,13 +63,46 @@
 
     @Option(
         name = "allow_multiple",
-        converter = Converters.AssignmentConverter.class,
+        converter = StarlarkAssignmentConverter.class,
         defaultValue = "",
         allowMultiple = true,
-        documentationCategory = OptionDocumentationCategory.OUTPUT_PARAMETERS,
-        effectTags = {OptionEffectTag.CHANGES_INPUTS, OptionEffectTag.AFFECTS_OUTPUTS},
-        help = "Each --define option specifies an assignment for a build variable.")
+        documentationCategory = OptionDocumentationCategory.UNDOCUMENTED,
+        effectTags = {OptionEffectTag.NO_OP},
+        help = "An option that mimics the behavior of --define (allowMultiple=true + converter).")
     public List<Map.Entry<String, String>> allowMultiple;
+
+    @Option(
+        name = "foo",
+        defaultValue = "",
+        documentationCategory = OptionDocumentationCategory.UNDOCUMENTED,
+        effectTags = {OptionEffectTag.NO_OP},
+        help = "A simple option for basic testing.")
+    public String foo;
+
+    /** TestObject to expose to Starlark. */
+    static class FooObject {}
+
+    /** A converter from String -> FooObject for foo_object option */
+    public static class FooConverter implements Converter<FooObject> {
+      @Override
+      public FooObject convert(String input) throws OptionsParsingException {
+        return new FooObject();
+      }
+
+      @Override
+      public String getTypeDescription() {
+        return "";
+      }
+    }
+
+    @Option(
+        name = "foo_object",
+        converter = FooConverter.class,
+        defaultValue = "",
+        documentationCategory = OptionDocumentationCategory.UNDOCUMENTED,
+        effectTags = {OptionEffectTag.NO_OP},
+        help = "An option with a non-Starlark friendly java form.")
+    public FooObject fooObject;
   }
 
   /** Loads a new {link @DummyTestFragment} instance. */
@@ -94,6 +129,7 @@
     ConfiguredRuleClassProvider.Builder builder = new ConfiguredRuleClassProvider.Builder();
     TestRuleClassProvider.addStandardRules(builder);
     builder.addConfigurationFragment(new DummyTestLoader());
+    builder.addConfigurationOptions(BuildConfiguration.Options.class);
     return builder.build();
   }
 
@@ -927,4 +963,123 @@
         .containsExactly(
             Maps.immutableEntry("APRIL", "SHOWERS"), Maps.immutableEntry("MAY", "FLOWERS"));
   }
+
+  @Test
+  public void testReadNativeOption_allowMultipleOptions() throws Exception {
+    writeWhitelistFile();
+    scratch.file(
+        "test/transitions.bzl",
+        "def _impl(settings, attr):",
+        "  if settings['//command_line_option:allow_multiple']['APRIL'] == 'FOOLS':",
+        "    return {",
+        "      '//command_line_option:foo': 'post-transition'",
+        "    }",
+        "  else:",
+        "    return {",
+        "      '//command_line_option:foo': ''",
+        "    }",
+        "my_transition = transition(",
+        "  implementation = _impl,",
+        "  inputs = ['//command_line_option:allow_multiple'],",
+        "  outputs = ['//command_line_option:foo'])");
+    scratch.file(
+        "test/rules.bzl",
+        "load('//test:transitions.bzl', 'my_transition')",
+        "def _impl(ctx):",
+        "  return []",
+        "my_rule = rule(",
+        "  implementation = _impl,",
+        "  cfg = my_transition,",
+        "  attrs = {",
+        "    '_whitelist_function_transition': attr.label(",
+        "        default = '//tools/whitelists/function_transition_whitelist',",
+        "    ),",
+        "  })");
+    scratch.file("test/BUILD", "load('//test:rules.bzl', 'my_rule')", "my_rule(name = 'test')");
+
+    useConfiguration("--allow_multiple=APRIL=FOOLS");
+
+    BuildConfiguration configuration = getConfiguration(getConfiguredTarget("//test"));
+    assertThat(configuration.getOptions().get(DummyTestOptions.class).foo)
+        .isEqualTo("post-transition");
+  }
+
+  @Test
+  public void testReadNativeOption_testDefine() throws Exception {
+    writeWhitelistFile();
+    scratch.file(
+        "test/transitions.bzl",
+        "def _impl(settings, attr):",
+        "  if settings['//command_line_option:define']['APRIL'] == 'SHOWERS' and "
+            + "settings['//command_line_option:define']['MAY'] == 'FLOWERS':",
+        "    return {'//command_line_option:foo': 'post-transition'}",
+        "  else:",
+        "    return {",
+        "      '//command_line_option:foo': ''",
+        "    }",
+        "my_transition = transition(",
+        "  implementation = _impl,",
+        "  inputs = ['//command_line_option:define'],",
+        "  outputs = ['//command_line_option:foo'])");
+    scratch.file(
+        "test/rules.bzl",
+        "load('//test:transitions.bzl', 'my_transition')",
+        "def _impl(ctx):",
+        "  return []",
+        "my_rule = rule(",
+        "  implementation = _impl,",
+        "  cfg = my_transition,",
+        "  attrs = {",
+        "    '_whitelist_function_transition': attr.label(",
+        "        default = '//tools/whitelists/function_transition_whitelist',",
+        "    ),",
+        "  })");
+    scratch.file("test/BUILD", "load('//test:rules.bzl', 'my_rule')", "my_rule(name = 'test')");
+
+    useConfiguration("--define=APRIL=SHOWERS", "--define=MAY=MORE_SHOWERS");
+
+    BuildConfiguration configuration = getConfiguration(getConfiguredTarget("//test"));
+    assertThat(configuration.getOptions().get(DummyTestOptions.class).foo).isEmpty();
+
+    useConfiguration("--define=APRIL=SHOWERS", "--define=MAY=FLOWERS");
+
+    configuration = getConfiguration(getConfiguredTarget("//test"));
+    assertThat(configuration.getOptions().get(DummyTestOptions.class).foo)
+        .isEqualTo("post-transition");
+  }
+
+  @Test
+  public void testReadNativeOption_noStarlarkConverter() throws Exception {
+    writeWhitelistFile();
+    scratch.file(
+        "test/transitions.bzl",
+        "def _impl(settings, attr):",
+        "  return {",
+        "    '//command_line_option:foo_object': settings['//command_line_option:foo_object'] ",
+        "  }",
+        "my_transition = transition(",
+        "  implementation = _impl,",
+        "  inputs = ['//command_line_option:foo_object'],",
+        "  outputs = ['//command_line_option:foo_object'])");
+    scratch.file(
+        "test/rules.bzl",
+        "load('//test:transitions.bzl', 'my_transition')",
+        "def _impl(ctx):",
+        "  return []",
+        "my_rule = rule(",
+        "  implementation = _impl,",
+        "  cfg = my_transition,",
+        "  attrs = {",
+        "    '_whitelist_function_transition': attr.label(",
+        "        default = '//tools/whitelists/function_transition_whitelist',",
+        "    ),",
+        "  })");
+    scratch.file("test/BUILD", "load('//test:rules.bzl', 'my_rule')", "my_rule(name = 'test')");
+
+    reporter.removeHandler(failFastHandler);
+    getConfiguredTarget("//test");
+    assertContainsEvent(
+        "Unable to read option '//command_line_option:foo_object' -  option"
+            + " '//command_line_option:foo_object' is Starlark incompatible");
+  }
 }