diff --git a/tmt/steps/__init__.py b/tmt/steps/__init__.py
index 14964a0adc..f582b5e05e 100644
--- a/tmt/steps/__init__.py
+++ b/tmt/steps/__init__.py
@@ -1958,7 +1958,16 @@ def _login(
             # Attempt to push the workdir to the guest
             try:
                 guest.push()
-                cwd = cwd or self.parent.plan.worktree
+                if not cwd:
+                    worktree = self.parent.plan.worktree
+                    tests = self.parent.plan.discover.tests()
+                    test_path = tests[-1].path if tests else None
+
+                    if worktree and test_path:
+                        cwd = worktree.parent / "discover" / test_path.unrooted()
+                    else:
+                        cwd = worktree
+
             except tmt.utils.GeneralError:
                 self.warn("Failed to push workdir to the guest.")
                 cwd = None