diff --git a/compiler/ir/backend.js/src/org/jetbrains/kotlin/ir/backend/js/transformers/irToJs/CompilationOutputs.kt b/compiler/ir/backend.js/src/org/jetbrains/kotlin/ir/backend/js/transformers/irToJs/CompilationOutputs.kt
index 1ed89b61b1e..de549eb4be1 100644
--- a/compiler/ir/backend.js/src/org/jetbrains/kotlin/ir/backend/js/transformers/irToJs/CompilationOutputs.kt
+++ b/compiler/ir/backend.js/src/org/jetbrains/kotlin/ir/backend/js/transformers/irToJs/CompilationOutputs.kt
@@ -35,7 +35,7 @@ abstract class CompilationOutputs {
         fun File.writeAsJsFile(out: CompilationOutputs) {
             parentFile.mkdirs()
             val jsMapFile = mapForJsFile
-            val jsFile = canonicalFile
+            val jsFile = normalizedAbsoluteFile
             out.writeJsCode(jsFile, jsMapFile)
 
             writtenFiles += jsFile
@@ -65,11 +65,14 @@ abstract class CompilationOutputs {
         return allTsDefinitions.toTypeScript(moduleName, moduleKind)
     }
 
+    private val File.normalizedAbsoluteFile
+        get() = absoluteFile.normalize()
+
     private val File.mapForJsFile
-        get() = resolveSibling("$name.map").canonicalFile
+        get() = resolveSibling("$name.map").normalizedAbsoluteFile
 
     private val File.dtsForJsFile
-        get() = resolveSibling("$nameWithoutExtension.d.ts").canonicalFile
+        get() = resolveSibling("$nameWithoutExtension.d.ts").normalizedAbsoluteFile
 }
 
 private fun File.copyModificationTimeFrom(from: File) {
diff --git a/js/js.sourcemap/src/org/jetbrains/kotlin/js/sourceMap/RelativePathCalculator.kt b/js/js.sourcemap/src/org/jetbrains/kotlin/js/sourceMap/RelativePathCalculator.kt
index 53ee42952d1..c88c02c9fb2 100644
--- a/js/js.sourcemap/src/org/jetbrains/kotlin/js/sourceMap/RelativePathCalculator.kt
+++ b/js/js.sourcemap/src/org/jetbrains/kotlin/js/sourceMap/RelativePathCalculator.kt
@@ -8,20 +8,22 @@ package org.jetbrains.kotlin.js.sourceMap
 import java.io.File
 
 class RelativePathCalculator(baseDir: File) {
-    private val baseDirPath = generateSequence(baseDir.canonicalFile) { it.parentFile }.toList().asReversed()
+    private fun File.getAllParents() = generateSequence(absoluteFile.normalize()) { it.parentFile }.toList().asReversed()
+
+    private val baseDirPath = baseDir.getAllParents()
 
     fun calculateRelativePathTo(file: File): String? {
-        val path = generateSequence(file.canonicalFile) { it.parentFile }.toList().asReversed()
-        if (baseDirPath[0] != path[0]) return null
+        val parents = file.getAllParents()
+        if (baseDirPath[0] != parents[0]) return null
 
-        val commonLength = baseDirPath.zip(path).takeWhile { (first, second) -> first == second }.size
+        val commonLength = baseDirPath.zip(parents).count { (first, second) -> first == second }
 
         val sb = StringBuilder()
         for (i in commonLength until baseDirPath.size) {
             sb.append("../")
         }
-        for (i in commonLength until path.size) {
-            sb.append(path[i].name).append('/')
+        for (i in commonLength until parents.size) {
+            sb.append(parents[i].name).append('/')
         }
         sb.setLength(sb.lastIndex)