diff --git a/compiler/src/dotty/tools/io/Path.scala b/compiler/src/dotty/tools/io/Path.scala
index e632bf488ec9..208b18078b7e 100644
--- a/compiler/src/dotty/tools/io/Path.scala
+++ b/compiler/src/dotty/tools/io/Path.scala
@@ -126,9 +126,33 @@ class Path private[io] (val jpath: JPath) {
   /**
    * @return The path of the parent directory, or root if path is already root
    */
-  def parent: Directory = jpath.normalize.getParent match {
-    case null => Directory(jpath)
-    case parent => Directory(parent)
+  def parent: Directory = {
+    // We don't call JPath#normalize here because it may result in resolving
+    // to a different path than intended, such as when the given path contains
+    // a `..` component and the preceding name is a symbolic link.
+    // https://docs.oracle.com/javase/8/docs/api/java/nio/file/Path.html#normalize--
+    //
+    // Paths ending with `..` or `.` are handled specially here as
+    // JPath#getParent wants to simply strip away that last element.
+    // For the `..` case, we should take care not to fall into the above trap
+    // as the preceding name may be a symbolic link. This leaves little choice
+    // (since we don't want to access the file system) but to return the given
+    // path with `..` appended. By contrast, a `.` as the final path element
+    // is always redundant and should be removed before computing the parent.
+    if path.isEmpty then
+      Directory("..")
+    else if jpath.endsWith("..") then
+      (this / "..").toDirectory
+    else if jpath.endsWith(".") then
+      jpath.getParent match   // strip the trailing `.` element
+        case null => Directory("..")
+        case p    => new Path(p).parent
+    else jpath.getParent match
+      case null =>
+        if isAbsolute then toDirectory  // it should be a root
+        else Directory(".")
+      case x =>
+        Directory(x)
   }
   def parents: List[Directory] = {
     val p = parent
diff --git a/compiler/test/dotty/tools/io/PathTest.scala b/compiler/test/dotty/tools/io/PathTest.scala
new file mode 100644
index 000000000000..731d29cee8e6
--- /dev/null
+++ b/compiler/test/dotty/tools/io/PathTest.scala
@@ -0,0 +1,49 @@
+package dotty.tools.io
+
+import org.junit.Test
+
+class PathTest {
+  // Ref https://github.com/lampepfl/dotty/issues/11644#issuecomment-792457275
+  @Test def parent(): Unit = {
+    testParent(Path(""), Directory(".."))
+    testParent(Path("."), Directory(".."))
+    testParent(Path(".") / ".", Directory(".."))
+    testParent(Path(".."), Directory("..") / "..")
+    testParent(Path("..") / ".", Directory("..") / "..")
+    testParent(Path("..") / "..", Directory("..") / ".." / "..")
+    testParent(Path(".") / "..",
+      Directory("..") / "..",
+      Directory(".") / ".." / "..")
+
+    testParent(Path("foo") / ".", Directory("."))
+    testParent(Path("foo") / ".." / "bar", Directory("foo") / "..")
+    testParent(Path("foo") / ".." / "." / "bar", Directory("foo") / ".." / ".")
+
+    testParent(Path("foo.txt"), Directory("."))
+    testParent(Path(".") / "foo.txt", Directory("."))
+    testParent(Path(".") / "baz" / "bar" / "foo.txt",
+      Directory(".") / "baz" / "bar",
+      Directory("baz") / "bar")
+
+    for (root <- Path.roots) {
+      testParent(root, root)
+      testParent(root / ".", root)
+      testParent(root / "..", root / ".." / "..")
+      testParent(root / "foo" / ".", root)
+      testParent(root / "foo.txt", root)
+      testParent(root / "baz" / "bar" / "foo.txt", root / "baz" / "bar")
+      testParent(root / "foo" / "bar" / "..",  root / "foo" / "bar" / ".." / "..")
+    }
+  }
+
+  /** The parent of a path may have multiple valid non-canonical representations.
+   *  Here we test that the parent of the specified path is among a curated list
+   *  of representations we consider to be valid.
+   */
+  private def testParent(path: Path, expected: Path*): Unit = {
+    val actual = path.parent
+    val some = if (expected.length > 1) " one of" else ""
+    assert(expected.contains(actual),
+      s"""expected$some: ${expected.mkString("<",">, <",">")} but was: <$actual>""")
+  }
+}
diff --git a/project/scripts/bootstrapCmdTests b/project/scripts/bootstrapCmdTests
index d4d7313d300c..7683c53f9e82 100755
--- a/project/scripts/bootstrapCmdTests
+++ b/project/scripts/bootstrapCmdTests
@@ -37,6 +37,7 @@ clear_out "$OUT"
 # check that `scalac -from-tasty` compiles and `scala` runs it
 echo "testing ./bin/scalac -from-tasty and scala -classpath"
 clear_out "$OUT1"
+./bin/scalac "$SOURCE" -d "$OUT"
 ./bin/scalac -from-tasty -d "$OUT1" "$OUT/$TASTY"
 ./bin/scala -classpath "$OUT1" "$MAIN" > "$tmp"
 test "$EXPECTED_OUTPUT" = "$(cat "$tmp")"
@@ -57,3 +58,9 @@ grep -qe "def main(args: scala.Array\[scala.Predef.String\]): scala.Unit =" "$tm
 echo "testing ./bin/scaladoc"
 clear_out "$OUT1"
 ./bin/scaladoc -project Hello -d "$OUT1" "$OUT/out.jar"
+
+# check compilation when the class/tasty files already exist in the current directory
+echo "testing i11644"
+cwd=$(pwd)
+clear_out "$OUT"
+(cd "$OUT" && "$cwd/bin/scalac" "$cwd/tests/pos/i11644.scala" && "$cwd/bin/scalac" "$cwd/tests/pos/i11644.scala")
diff --git a/project/scripts/cmdTestsCommon.inc.sh b/project/scripts/cmdTestsCommon.inc.sh
index 1247481aec12..dc81a3e35b52 100644
--- a/project/scripts/cmdTestsCommon.inc.sh
+++ b/project/scripts/cmdTestsCommon.inc.sh
@@ -15,5 +15,5 @@ tmp=$(mktemp)
 clear_out()
 {
   local out="$1"
-  rm -rf "$out/*"
+  rm -rf "$out"/*
 }
diff --git a/tests/pos/i11644.scala b/tests/pos/i11644.scala
new file mode 100644
index 000000000000..3e0b75e49e37
--- /dev/null
+++ b/tests/pos/i11644.scala
@@ -0,0 +1 @@
+@main def hello = println("hello, world")