diff --git a/platform/lang-api/src/com/intellij/execution/target/TargetEnvironmentPaths.kt b/platform/lang-api/src/com/intellij/execution/target/TargetEnvironmentPaths.kt
index b3c95f3b741b..8337bb6f3b89 100644
--- a/platform/lang-api/src/com/intellij/execution/target/TargetEnvironmentPaths.kt
+++ b/platform/lang-api/src/com/intellij/execution/target/TargetEnvironmentPaths.kt
@@ -54,8 +54,26 @@ private fun findPathVariants(mappings: Iterable<PathMapping>,
 }
 
 internal fun joinTargetPaths(basePath: String, relativePath: String, fileSeparator: Char): String {
-  val resultCanonicalPath = FileUtil.toCanonicalPath("$basePath$fileSeparator$relativePath", fileSeparator)
-  // The method `FileUtil.toCanonicalPath()` returns the path with '/' no matter what `fileSeparator` is passed but let's make the result
-  // system-dependent
-  return FileUtil.toSystemDependentName(resultCanonicalPath, fileSeparator)
-}
\ No newline at end of file
+  val normalizedBasePathForJoining = basePath
+    .normalizeFileSeparatorCharacter(fileSeparator)
+    .removeRepetitiveFileSeparators(fileSeparator)
+    .ensureEndsWithFileSeparator(fileSeparator)
+  val normalizedRelativePath = relativePath
+    .normalizeFileSeparatorCharacter(fileSeparator)
+    .removeRepetitiveFileSeparators(fileSeparator)
+    .normalizeRelativePath(fileSeparator)
+  return "$normalizedBasePathForJoining$normalizedRelativePath"
+}
+
+private fun String.normalizeFileSeparatorCharacter(fileSeparator: Char): String = if (fileSeparator == '\\') replace('/', fileSeparator) else this
+
+private fun String.removeRepetitiveFileSeparators(fileSeparator: Char): String = replace("$fileSeparator$fileSeparator", fileSeparator.toString())
+
+private fun String.normalizeRelativePath(fileSeparator: Char): String =
+  when {
+    length == 1 && this[0] == '.' -> ""
+    startsWith(prefix = ".$fileSeparator") -> substring(startIndex = 2)
+    else -> this
+  }.removeSuffix(fileSeparator.toString())
+
+private fun String.ensureEndsWithFileSeparator(fileSeparator: Char): String = if (endsWith(fileSeparator)) this else "$this$fileSeparator"
\ No newline at end of file
diff --git a/platform/lang-api/testSources/com/intellij/execution/target/TargetEnvironmentPathsJoinFunctionTest.kt b/platform/lang-api/testSources/com/intellij/execution/target/TargetEnvironmentPathsJoinFunctionTest.kt
index 82f19394fa8d..86758d7dba99 100644
--- a/platform/lang-api/testSources/com/intellij/execution/target/TargetEnvironmentPathsJoinFunctionTest.kt
+++ b/platform/lang-api/testSources/com/intellij/execution/target/TargetEnvironmentPathsJoinFunctionTest.kt
@@ -27,18 +27,24 @@ class TargetEnvironmentPathsJoinFunctionTest(private val basePath: String,
       arrayOf("/foo/", "bar/", '/', "/foo/bar"),
 
       arrayOf("/", ".", '/', "/"),
-      arrayOf("/", "..", '/', "/"),
 
       arrayOf("C:\\", ".", '\\', "C:\\"),
       arrayOf("C:\\\\", ".", '\\', "C:\\"),
-      arrayOf("C:\\", "..", '\\', "C:\\"),
-      arrayOf("C:\\\\", "..", '\\', "C:\\"),
       arrayOf("C:\\", "foo", '\\', "C:\\foo"),
       arrayOf("C:\\", "foo\\", '\\', "C:\\foo"),
 
+      arrayOf("C:/", ".", '\\', "C:\\"),
+      arrayOf("C://", ".", '\\', "C:\\"),
+      arrayOf("C:/", "foo", '\\', "C:\\foo"),
+      arrayOf("C:", "foo/", '\\', "C:\\foo"),
+
       arrayOf("C:\\", "Directory With Spaces\\", '\\', "C:\\Directory With Spaces"),
       arrayOf("C:\\Directory With Spaces", "File With Spaces.txt", '\\', "C:\\Directory With Spaces\\File With Spaces.txt"),
-      arrayOf("C:\\Directory With Spaces", "Subdirectory With Spaces\\", '\\', "C:\\Directory With Spaces\\Subdirectory With Spaces")
+      arrayOf("C:\\Directory With Spaces", "Subdirectory With Spaces\\", '\\', "C:\\Directory With Spaces\\Subdirectory With Spaces"),
+
+      arrayOf("C:/", "Directory With Spaces/", '\\', "C:\\Directory With Spaces"),
+      arrayOf("C:/Directory With Spaces", "File With Spaces.txt", '\\', "C:\\Directory With Spaces\\File With Spaces.txt"),
+      arrayOf("C:/Directory With Spaces", "Subdirectory With Spaces/", '\\', "C:\\Directory With Spaces\\Subdirectory With Spaces"),
     )
   }
 }
\ No newline at end of file