diff --git a/scalafix-cli/src/main/scala/scalafix/cli/CliRunner.scala b/scalafix-cli/src/main/scala/scalafix/cli/CliRunner.scala
index 9314f946c..43c112faf 100644
--- a/scalafix-cli/src/main/scala/scalafix/cli/CliRunner.scala
+++ b/scalafix-cli/src/main/scala/scalafix/cli/CliRunner.scala
@@ -141,6 +141,7 @@ sealed abstract case class CliRunner(
           case WriteMode.WriteFile =>
             val outFile = replacePath(input.original.path)
             if (isUpToDate(input)) {
+              Files.createDirectories(outFile.toNIO)
               Files.write(outFile.toNIO, fixed.getBytes(input.original.charset))
               ExitStatus.Ok
             } else {
@@ -449,13 +450,22 @@ object CliRunner {
       }
 
     val resolvedPathReplace: Configured[AbsolutePath => AbsolutePath] = try {
-      val outFromPattern = Pattern.compile(outFrom.getOrElse(""))
-      def replacePath(file: AbsolutePath): AbsolutePath =
-        AbsolutePath(
-          outFromPattern
-            .matcher(file.toString())
-            .replaceAll(outTo.getOrElse("")))
-      Ok(replacePath _)
+      (outFrom, outTo) match {
+        case (None, None) => Ok(identity[AbsolutePath])
+        case (Some(from), Some(to)) =>
+          val outFromPattern = Pattern.compile(from)
+          def replacePath(file: AbsolutePath): AbsolutePath =
+            AbsolutePath(outFromPattern.matcher(file.toString()).replaceAll(to))
+          Ok(replacePath _)
+        case (Some(from), _) =>
+          ConfError
+            .msg(s"--out-from $from must be accompanied with --out-to")
+            .notOk
+        case (_, Some(to)) =>
+          ConfError
+            .msg(s"--out-to $to must be accompanied with --out-from")
+            .notOk
+      }
     } catch {
       case e: PatternSyntaxException =>
         ConfError.msg(s"Invalid regex '$outFrom'! ${e.getMessage}").notOk
diff --git a/scalafix-tests/unit/src/test/scala/scalafix/cli/BaseCliTest.scala b/scalafix-tests/unit/src/test/scala/scalafix/cli/BaseCliTest.scala
index dd4902f16..ad53b30df 100644
--- a/scalafix-tests/unit/src/test/scala/scalafix/cli/BaseCliTest.scala
+++ b/scalafix-tests/unit/src/test/scala/scalafix/cli/BaseCliTest.scala
@@ -61,9 +61,9 @@ trait BaseCliTest extends FunSuite with DiffAssertions {
             out = new PrintStream(out)
           ))
       val obtained = StringFS.dir2string(root)
+      assert(exit == expectedExit)
       assertNoDiff(obtained, expectedLayout)
       outputAssert(out.toString)
-      assert(exit == expectedExit)
     }
   }
 
@@ -106,9 +106,9 @@ trait BaseCliTest extends FunSuite with DiffAssertions {
             if (fileIsFixed) BuildInfo.outputSourceroot
             else BuildInfo.inputSourceroot
           ).resolve(removeImportsPath))
+      assert(exit == expectedExit)
       assertNoDiff(obtained, expected)
       outputAssert(out.toString())
-      assert(exit == expectedExit)
     }
   }
 
diff --git a/scalafix-tests/unit/src/test/scala/scalafix/cli/CliSyntaxTest.scala b/scalafix-tests/unit/src/test/scala/scalafix/cli/CliSyntaxTest.scala
index c884be8e0..6884a1b47 100644
--- a/scalafix-tests/unit/src/test/scala/scalafix/cli/CliSyntaxTest.scala
+++ b/scalafix-tests/unit/src/test/scala/scalafix/cli/CliSyntaxTest.scala
@@ -212,4 +212,29 @@ class CliSyntaxTest extends BaseCliTest {
       assert(output.contains("No files to fix!") && output.contains("dir"))
     }
   )
+
+  check(
+    name = "--out-from --out-to change output path",
+    originalLayout = """
+                       |/src/shared/a.scala
+                       |object a { def foo { println(1) } }
+                       |""".stripMargin,
+    args = List(
+      "-r",
+      ProcedureSyntax.toString,
+      "--out-from",
+      "shared",
+      "--out-to",
+      "fixed",
+      "src"
+    ),
+    expectedLayout = """
+                       |/src/fixed/a.scala
+                       |object a { def foo: Unit = { println(1) } }
+                       |
+                       |/src/shared/a.scala
+                       |object a { def foo { println(1) } }
+                       |""".stripMargin,
+    expectedExit = ExitStatus.Ok
+  )
 }