diff --git a/Lib/dataclasses.py b/Lib/dataclasses.py
index 3ccb72469286eb..730ced7299865e 100644
--- a/Lib/dataclasses.py
+++ b/Lib/dataclasses.py
@@ -550,7 +550,12 @@ def __annotate__(format, /):
 
                 new_annotations = {}
                 for k in annotation_fields:
-                    new_annotations[k] = cls_annotations[k]
+                    # gh-142214: The annotation may be missing in unusual dynamic cases.
+                    # If so, just skip it.
+                    try:
+                        new_annotations[k] = cls_annotations[k]
+                    except KeyError:
+                        pass
 
                 if return_type is not MISSING:
                     if format == Format.STRING:
@@ -1399,9 +1404,10 @@ def _add_slots(cls, is_frozen, weakref_slot, defined_fields):
             f.type = ann
 
     # Fix the class reference in the __annotate__ method
-    init_annotate = newcls.__init__.__annotate__
-    if getattr(init_annotate, "__generated_by_dataclasses__", False):
-        _update_func_cell_for__class__(init_annotate, cls, newcls)
+    init = newcls.__init__
+    if init_annotate := getattr(init, "__annotate__", None):
+        if getattr(init_annotate, "__generated_by_dataclasses__", False):
+            _update_func_cell_for__class__(init_annotate, cls, newcls)
 
     return newcls
 
diff --git a/Lib/test/test_dataclasses/__init__.py b/Lib/test/test_dataclasses/__init__.py
index 513dd78c4381b4..3b335429b98500 100644
--- a/Lib/test/test_dataclasses/__init__.py
+++ b/Lib/test/test_dataclasses/__init__.py
@@ -927,6 +927,20 @@ class C:
 
         validate_class(C)
 
+    def test_incomplete_annotations(self):
+        # gh-142214
+        @dataclass
+        class C:
+            "doc"  # needed because otherwise we fetch the annotations at the wrong time
+            x: int
+
+        C.__annotate__ = lambda _: {}
+
+        self.assertEqual(
+            annotationlib.get_annotations(C.__init__),
+            {"return": None}
+        )
+
     def test_missing_default(self):
         # Test that MISSING works the same as a default not being
         #  specified.
@@ -2578,6 +2592,20 @@ def __init__(self, x: int) -> None:
 
         self.assertFalse(hasattr(E.__init__.__annotate__, "__generated_by_dataclasses__"))
 
+    def test_slots_true_init_false(self):
+        # Test that slots=True and init=False work together and
+        #  that __annotate__ is not added to __init__.
+
+        @dataclass(slots=True, init=False)
+        class F:
+            x: int
+
+        f = F()
+        f.x = 10
+        self.assertEqual(f.x, 10)
+
+        self.assertFalse(hasattr(F.__init__, "__annotate__"))
+
     def test_init_false_forwardref(self):
         # Test forward references in fields not required for __init__ annotations.
 
diff --git a/Misc/NEWS.d/next/Build/2025-11-25-13-17-47.gh-issue-141926.KmuM2h.rst b/Misc/NEWS.d/next/Build/2025-11-25-13-17-47.gh-issue-141926.KmuM2h.rst
new file mode 100644
index 00000000000000..dab79ba5cf949d
--- /dev/null
+++ b/Misc/NEWS.d/next/Build/2025-11-25-13-17-47.gh-issue-141926.KmuM2h.rst
@@ -0,0 +1,4 @@
+``RUNSHARED`` is no longer cleared when cross-compiling. Previously,
+``RUNSHARED`` was cleared when cross-compiling, which breaks PGO when using
+``--enabled-shared`` on systems where the cross-compiled CPython is otherwise
+executable (e.g., via transparent emulation).
diff --git a/Misc/NEWS.d/next/Library/2025-12-03-06-12-39.gh-issue-142214.appYNZ.rst b/Misc/NEWS.d/next/Library/2025-12-03-06-12-39.gh-issue-142214.appYNZ.rst
new file mode 100644
index 00000000000000..b87430ec1a3d65
--- /dev/null
+++ b/Misc/NEWS.d/next/Library/2025-12-03-06-12-39.gh-issue-142214.appYNZ.rst
@@ -0,0 +1,12 @@
+Fix two regressions in :mod:`dataclasses` in Python 3.14.1 related to
+annotations.
+
+* An exception is no longer raised if ``slots=True`` is used and the
+  ``__init__`` method does not have an ``__annotate__`` attribute
+  (likely because ``init=False`` was used).
+
+* An exception is no longer raised if annotations are requested on the
+  ``__init__`` method and one of the fields is not present in the class
+  annotations. This can occur in certain dynamic scenarios.
+
+Patch by Jelle Zijlstra.
diff --git a/configure b/configure
index 620878bb181378..1561f7f4134ac2 100755
--- a/configure
+++ b/configure
@@ -7808,10 +7808,6 @@ fi
 { printf "%s\n" "$as_me:${as_lineno-$LINENO}: result: $LDLIBRARY" >&5
 printf "%s\n" "$LDLIBRARY" >&6; }
 
-if test "$cross_compiling" = yes; then
-  RUNSHARED=
-fi
-
 # HOSTRUNNER - Program to run CPython for the host platform
 { printf "%s\n" "$as_me:${as_lineno-$LINENO}: checking HOSTRUNNER" >&5
 printf %s "checking HOSTRUNNER... " >&6; }
diff --git a/configure.ac b/configure.ac
index 8ef479fe32036c..f2a7319d22d24b 100644
--- a/configure.ac
+++ b/configure.ac
@@ -1639,10 +1639,6 @@ else # shared is disabled
 fi
 AC_MSG_RESULT([$LDLIBRARY])
 
-if test "$cross_compiling" = yes; then
-  RUNSHARED=
-fi
-
 # HOSTRUNNER - Program to run CPython for the host platform
 AC_MSG_CHECKING([HOSTRUNNER])
 if test -z "$HOSTRUNNER"