diff --git a/dvc/cache/base.py b/dvc/cache/base.py
index 5dca5a096..6f3240da0 100644
--- a/dvc/cache/base.py
+++ b/dvc/cache/base.py
@@ -537,6 +537,7 @@ class CloudCache:
         progress_callback=None,
         relink=False,
         filter_info=None,
+        quiet=False,
     ):
         if path_info.scheme not in ["local", self.tree.scheme]:
             raise NotImplementedError
@@ -544,10 +545,11 @@ class CloudCache:
         failed = None
         skip = False
         if not hash_info:
-            logger.warning(
-                "No file hash info found for '%s'. " "It won't be created.",
-                path_info,
-            )
+            if not quiet:
+                logger.warning(
+                    "No file hash info found for '%s'. It won't be created.",
+                    path_info,
+                )
             self.safe_remove(path_info, force=force)
             failed = path_info
 
@@ -558,11 +560,12 @@ class CloudCache:
         elif self.changed_cache(
             hash_info, path_info=path_info, filter_info=filter_info
         ):
-            logger.warning(
-                "Cache '%s' not found. File '%s' won't be created.",
-                hash_info,
-                path_info,
-            )
+            if not quiet:
+                logger.warning(
+                    "Cache '%s' not found. File '%s' won't be created.",
+                    hash_info,
+                    path_info,
+                )
             self.safe_remove(path_info, force=force)
             failed = path_info
 
diff --git a/dvc/output/base.py b/dvc/output/base.py
index e57c7ba29..24af234bc 100644
--- a/dvc/output/base.py
+++ b/dvc/output/base.py
@@ -330,6 +330,7 @@ class BaseOutput:
         relink=False,
         filter_info=None,
         allow_missing=False,
+        **kwargs,
     ):
         if not self.use_cache:
             if progress_callback:
@@ -346,6 +347,7 @@ class BaseOutput:
                 progress_callback=progress_callback,
                 relink=relink,
                 filter_info=filter_info,
+                **kwargs,
             )
         except CheckoutError:
             if allow_missing:
diff --git a/dvc/repo/checkout.py b/dvc/repo/checkout.py
index 58576412d..6b2914031 100644
--- a/dvc/repo/checkout.py
+++ b/dvc/repo/checkout.py
@@ -47,6 +47,7 @@ def checkout(
     relink=False,
     recursive=False,
     allow_missing=False,
+    **kwargs,
 ):
     from dvc.stage.exceptions import (
         StageFileBadNameError,
@@ -98,6 +99,7 @@ def checkout(
                 relink=relink,
                 filter_info=filter_info,
                 allow_missing=allow_missing,
+                **kwargs,
             )
             for key, items in result.items():
                 stats[key].extend(_fspath_dir(path) for path in items)
diff --git a/dvc/repo/experiments/__init__.py b/dvc/repo/experiments/__init__.py
index b1b5d704d..b6ab1d43c 100644
--- a/dvc/repo/experiments/__init__.py
+++ b/dvc/repo/experiments/__init__.py
@@ -403,7 +403,7 @@ class Experiments:
         )
         exp_rev = first(results)
         if exp_rev is not None:
-            self.checkout_exp(exp_rev, allow_missing=checkpoint)
+            self.checkout_exp(exp_rev)
         return results
 
     def reproduce_queued(self, **kwargs):
@@ -753,7 +753,7 @@ class Experiments:
             raise UploadError(fails)
 
     @scm_locked
-    def checkout_exp(self, rev, allow_missing=False):
+    def checkout_exp(self, rev, **kwargs):
         """Checkout an experiment to the user's workspace."""
         from git.exc import GitCommandError
 
@@ -762,12 +762,17 @@ class Experiments:
         baseline_rev = self._check_baseline(rev)
         self._scm_checkout(rev)
 
+        branch = self._get_branch_containing(rev)
+        m = self.BRANCH_RE.match(branch)
+        if m and m.group("checkpoint"):
+            kwargs.update({"allow_missing": True, "quiet": True})
+
         tmp = tempfile.NamedTemporaryFile(delete=False).name
         self.scm.repo.head.commit.diff(
             baseline_rev, patch=True, full_index=True, binary=True, output=tmp
         )
 
-        dirty = self.repo.scm.is_dirty()
+        dirty = self.repo.scm.is_dirty(untracked_files=True)
         if dirty:
             logger.debug("Stashing workspace changes.")
             self.repo.scm.repo.git.stash("push", "--include-untracked")
@@ -787,7 +792,7 @@ class Experiments:
                 self._unstash_workspace()
 
         if need_checkout:
-            dvc_checkout(self.repo, allow_missing=allow_missing)
+            dvc_checkout(self.repo, **kwargs)
 
     def _check_baseline(self, exp_rev):
         baseline_sha = self.repo.scm.get_rev()
@@ -852,12 +857,20 @@ class Experiments:
     def _get_branch_containing(self, rev):
         from git.exc import GitCommandError
 
-        if self.scm.repo.head.is_detached:
-            self._checkout_default_branch()
         try:
             names = self.scm.repo.git.branch(contains=rev).strip().splitlines()
+
+            if (
+                names
+                and self.scm.repo.head.is_detached
+                and names[0].startswith("* (HEAD detached")
+            ):
+                # Ignore detached head entry if it exists
+                del names[0]
+
             if not names:
                 return None
+
             if len(names) > 1:
                 raise MultipleBranchError(rev)
             name = names[0]
diff --git a/dvc/repo/experiments/executor.py b/dvc/repo/experiments/executor.py
index 111de674a..5cdacd54c 100644
--- a/dvc/repo/experiments/executor.py
+++ b/dvc/repo/experiments/executor.py
@@ -168,7 +168,9 @@ class LocalExecutor(ExperimentExecutor):
             #   is not polluted with the (persistent) out from an unrelated
             #   experiment run
             checkpoint = kwargs.pop("checkpoint", False)
-            dvc.checkout(allow_missing=checkpoint, force=checkpoint)
+            dvc.checkout(
+                allow_missing=checkpoint, force=checkpoint, quiet=checkpoint
+            )
             stages = dvc.reproduce(
                 on_unchanged=filter_pipeline,
                 allow_missing=checkpoint,