diff --git a/Dockerfile b/Dockerfile
index 71f3aad..cc45b53 100644
--- a/Dockerfile
+++ b/Dockerfile
@@ -2,7 +2,7 @@ FROM ubuntu:20.04
 
 LABEL maintainer="Drew Short <warrick@sothr.com>" \
     name="acm" \
-    version="1.2.0" \
+    version="1.4.0" \
     description="Prepackaged ACM with defaults and tooling"
 
 ENV LC_ALL=C.UTF-8
diff --git a/acm-config-default.json b/acm-config-default.json
index 1e0d125..3db8f91 100644
--- a/acm-config-default.json
+++ b/acm-config-default.json
@@ -3,26 +3,28 @@
   "profiles": {
     "default": {
       "jpeg": {
-        "version": "1.3.1",
+        "version": "1.4.0",
         "processors": ["cjpeg"],
         "extensions": [
           "jpg",
           "jpeg"
         ],
         "outputExtension": "jpg",
+        "forcePreserveSmallerInput": true,
         "command": "cjpeg -optimize -quality 90 -progressive -outfile {output_file} {input_file}"
       },
       "png": {
-        "version": "1.3.1",
+        "version": "1.4.0",
         "processors": ["optipng"],
         "extensions": [
           "png"
         ],
         "outputExtension": "png",
+        "forcePreserveSmallerInput": true,
         "command": "optipng -o2 -strip all -out {output_file} {input_file}"
       },
       "video": {
-        "version": "1.3.1",
+        "version": "1.4.0",
         "processors": ["ffmpeg"],
         "extensions": [
           "mp4",
@@ -32,7 +34,7 @@
         "command": "ffmpeg -hide_banner -loglevel panic -i {input_file} -c:v libvpx-vp9 -b:v 0 -crf 29 -c:a libopus {output_file}"
       },
       "audio": {
-        "version": "1.3.1",
+        "version": "1.4.0",
         "processors": ["ffmpeg", "opusenc"],
         "extensions": [
           "wav",
@@ -44,7 +46,7 @@
     },
     "placebo": {
       "jpeg": {
-        "version": "1.3.1",
+        "version": "1.4.0",
         "processors": ["cp"],
         "extensions": [
           "jpg",
@@ -52,20 +54,22 @@
         ],
         "outputExtension": "jpg",
         "preserveInputExtension": true,
-        "command": "cp {input_file} {output_file}"
+        "preserveSmallerInput": false,
+        "command": "cp {input_file} {output_file}",
       },
       "png": {
-        "version": "1.3.1",
+        "version": "1.4.0",
         "processors": ["cp"],
         "extensions": [
           "png"
         ],
         "outputExtension": "png",
         "preserveInputExtension": true,
+        "preserveSmallerInput": false,
         "command": "cp {input_file} {output_file}"
       },
       "video": {
-        "version": "1.3.1",
+        "version": "1.4.0",
         "processors": ["cp"],
         "extensions": [
           "mp4",
@@ -73,10 +77,11 @@
         ],
         "outputExtension": "mp4",
         "preserveInputExtension": true,
+        "preserveSmallerInput": false,
         "command": "cp {input_file} {output_file}"
       },
       "audio": {
-        "version": "1.3.1",
+        "version": "1.4.0",
         "processors": ["cp"],
         "extensions": [
           "wav",
@@ -84,12 +89,13 @@
         ],
         "outputExtension": "ogg",
         "preserveInputExtension": true,
+        "preserveSmallerInput": false,
         "command": "cp {input_file} {output_file}"
       }
     },
     "webp": {
       "jpeg": {
-        "version": "1.3.1",
+        "version": "1.4.0",
         "processors": ["cwebp"],
         "extensions": [
           "jpg",
@@ -99,7 +105,7 @@
         "command": "cwebp -jpeg_like -q 90 -o {output_file} {input_file}"
       },
       "png": {
-        "version": "1.3.1",
+        "version": "1.4.0",
         "processors": ["cwebp"],
         "extensions": [
           "png"
@@ -110,26 +116,28 @@
     },
     "aggressive": {
       "jpeg": {
-        "version": "1.3.1",
+        "version": "1.4.0",
         "processors": ["ffmpeg", "cjpeg"],
         "extensions": [
           "jpg",
           "jpeg"
         ],
         "outputExtension": "jpg",
+        "forcePreserveSmallerInput": true,
         "command": "export FILE={output_file} && export TEMP_FILE=${FILE}_tmp.jpg && ffmpeg -i {input_file} -vf scale=-1:720 ${TEMP_FILE} && cjpeg -optimize -quality 75 -progressive -outfile {output_file} ${TEMP_FILE} && rm ${TEMP_FILE}"
       },
       "png": {
-        "version": "1.3.1",
+        "version": "1.4.0",
         "processors": ["optipng"],
         "extensions": [
           "png"
         ],
         "outputExtension": "png",
+        "forcePreserveSmallerInput": true,
         "command": "optipng -o2 -strip all -out {output_file} {input_file}"
       },
       "video": {
-        "version": "1.3.1",
+        "version": "1.4.0",
         "processors": ["ffmpeg"],
         "extensions": [
           "mp4",
@@ -139,7 +147,7 @@
         "command": "ffmpeg -hide_banner -loglevel panic -i {input_file} -vf scale=-1:720 -c:v libvpx-vp9 -b:v 0 -crf 38 -c:a libopus {output_file}"
       },
       "audio": {
-        "version": "1.3.1",
+        "version": "1.4.0",
         "processors": ["ffmpeg", "opusenc"],
         "extensions": [
           "wav",
@@ -151,7 +159,7 @@
     },
     "aggressive-webp": {
       "jpeg": {
-        "version": "1.3.1",
+        "version": "1.4.0",
         "processors": ["cwebp"],
         "extensions": [
           "jpg",
@@ -161,7 +169,7 @@
         "command": "export FILE={output_file} && export TEMP_FILE=${FILE}_tmp.jpg && ffmpeg -i {input_file} -vf scale=-1:720 ${TEMP_FILE} && cwebp -jpeg_like -q 75 -o {output_file} ${TEMP_FILE} && rm ${TEMP_FILE}"
       },
       "png": {
-        "version": "1.3.1",
+        "version": "1.4.0",
         "processors": ["cwebp"],
         "extensions": [
           "png"
@@ -170,7 +178,7 @@
         "command": "cwebp -o {output_file} ${input_file}"
       },
       "video": {
-        "version": "1.3.1",
+        "version": "1.4.0",
         "processors": ["ffmpeg"],
         "extensions": [
           "mp4",
@@ -180,7 +188,7 @@
         "command": "ffmpeg -hide_banner -loglevel panic -i {input_file} -vf scale=-1:720 -c:v libvpx-vp9 -b:v 0 -crf 38 -c:a libopus {output_file}"
       },
       "audio": {
-        "version": "1.3.1",
+        "version": "1.4.0",
         "processors": ["ffmpeg", "opusenc"],
         "extensions": [
           "wav",
diff --git a/acm.py b/acm.py
index de461b6..048eb2b 100755
--- a/acm.py
+++ b/acm.py
@@ -5,6 +5,7 @@ import hashlib
 import io
 import json
 import os
+import pathlib
 import platform
 import sys
 import tempfile
@@ -18,7 +19,7 @@ from minio.error import NoSuchKey
 BUF_SIZE = 4096
 
 #Application Version
-VERSION = "1.3.1"
+VERSION = "1.4.0"
 
 
 ###########
@@ -27,7 +28,7 @@ VERSION = "1.3.1"
 
 
 async def run_command_shell(
-        command, stdout=asyncio.subprocess.PIPE, stderr=asyncio.subprocess.PIPE, on_success: Callable = ()):
+        command, stdout=asyncio.subprocess.PIPE, stderr=asyncio.subprocess.PIPE, on_success: List[Callable] = [()]):
     """Run command in subprocess (shell).
 
     Note:
@@ -41,7 +42,8 @@ async def run_command_shell(
     process_stdout, process_stderr = await process.communicate()
 
     if process.returncode == 0:
-        on_success()
+        for callable in on_success:
+            callable()
 
     if stdout != asyncio.subprocess.DEVNULL:
         result = process_stdout.decode().strip()
@@ -669,8 +671,9 @@ def compress_assets(ctx, profile, content, destination, print_input_and_identity
     if destination is None:
         destination = tempfile.mkdtemp()
 
-    compressed_files = []
+    task_output = []
     tasks = []
+    follow_up_tasks = []
 
     def store_filename(storage_list: List[str], filename: str):
         """
@@ -682,10 +685,35 @@ def compress_assets(ctx, profile, content, destination, print_input_and_identity
         """
         return lambda: storage_list.append(filename)
 
+    def queue_follow_up_task_if_keep_smaller_input(follow_up_tasks, input_file: str, output_file: str, keep_smaller_input: bool = True):
+        """
+        A lambda wrapper that handles keeping the smallest of the two files.
+        """
+        if keep_smaller_input:
+            command = f"cp {input_file} {output_file}"
+            return lambda: 
+                input_size = os.path.getsize(input_file)
+                output_size = os.path.getsize(output_file)
+                if output_size > input_size:
+                    follow_up_tasks.append(
+                        run_command_shell(
+                            command,
+                            stdout=asyncio.subprocess.DEVNULL,
+                            stderr=asyncio.subprocess.DEVNULL,
+                            on_success=[store_filename(
+                                task_output,
+                                f'Preserved smaller "{input_file}" {output_size} > {input_size}'
+                            )]
+                        )
+                    )
+        return None
+
+
     for input_file in files:
         for content_configuration in content_configurations:
             if any([input_file.endswith(extension) for extension in content_configuration['extensions']]):
                 file = input_file
+                file_extension = pathlib.Path(input_file).suffix
                 if 'REMOVE_PREFIX' in ctx.obj and ctx.obj['REMOVE_PREFIX'] is not None:
                     file = strip_prefix(ctx.obj['REMOVE_PREFIX'], input_file)
 
@@ -701,6 +729,19 @@ def compress_assets(ctx, profile, content, destination, print_input_and_identity
                 output_file_dir = os.path.dirname(output_file)
                 os.makedirs(output_file_dir, exist_ok=True)
 
+                if 'preserveSmallerInput' in content_configuration:
+                    preserve_smaller_input = bool(content_configuration['preserveSmallerInput'])
+                else:
+                    preserve_smaller_input = True
+
+                if 'forcePreserveSmallerInput' in content_configuration:
+                    force_preserve_smaller_input = bool(content_configuration['forcePreserveSmallerInput'])
+                else:
+                    force_preserve_smaller_input = False
+
+                # Only preserve the input if requested AND the extensions of the input and the output match
+                preserve_smaller_input = preserve_smaller_input and (force_preserve_smaller_input or file_extension == content_configuration["outputExtension"])
+
                 command: str = content_configuration['command'] \
                     .replace('{input_file}', f'\'{input_file}\'') \
                     .replace('{output_file}', f'\'{output_file}\'')
@@ -710,10 +751,15 @@ def compress_assets(ctx, profile, content, destination, print_input_and_identity
                         command,
                         stdout=asyncio.subprocess.DEVNULL,
                         stderr=asyncio.subprocess.DEVNULL,
-                        on_success=store_filename(
-                            compressed_files,
+                        on_success=[store_filename(
+                            task_output,
                             f'{input_file}\t{output_file_identity}' if print_input_and_identity else output_file
-                        )
+                        ),queue_follow_up_task_if_keep_smaller_input(
+                            follow_up_tasks,
+                            input_file,
+                            output_file,
+                            preserve_smaller_input
+                        )]
                     )
                 )
 
@@ -721,7 +767,11 @@ def compress_assets(ctx, profile, content, destination, print_input_and_identity
         tasks, max_concurrent_tasks=ctx.obj['CONFIG']['concurrency']
     )
 
-    print(os.linesep.join(compressed_files))
+    follow_up_results = run_asyncio_commands(
+        follow_up_tasks, max_concurrent_tasks=ctx.obj['CONFIG']['concurrency']
+    )
+
+    print(os.linesep.join(task_output))
 
 
 if __name__ == '__main__':
diff --git a/setup.py b/setup.py
index 9fcf464..d5bdd68 100644
--- a/setup.py
+++ b/setup.py
@@ -4,7 +4,7 @@ from distutils.core import setup
 
 setup(
     name='Asset-Compression-Manager',
-    version='1.3.1',
+    version='1.4.0',
     description='Helper Utility For Managing Compressed Assets',
     author='Drew Short',
     author_email='warrick@sothr.com'