diff --git a/README.md b/README.md
index 6b212f4..6593930 100644
--- a/README.md
+++ b/README.md
@@ -11,7 +11,7 @@ This package provides Python implementations of the following
 [ProseMirror](https://prosemirror.net/) packages:
 
 - [`prosemirror-model`](https://github.com/ProseMirror/prosemirror-model) version 1.18.1
-- [`prosemirror-transform`](https://github.com/ProseMirror/prosemirror-transform) version 1.7.1
+- [`prosemirror-transform`](https://github.com/ProseMirror/prosemirror-transform) version 1.7.5
 - [`prosemirror-test-builder`](https://github.com/ProseMirror/prosemirror-test-builder)
 - [`prosemirror-schema-basic`](https://github.com/ProseMirror/prosemirror-schema-basic) version 1.1.2
 - [`prosemirror-schema-list`](https://github.com/ProseMirror/prosemirror-schema-list)
diff --git a/prosemirror/transform/structure.py b/prosemirror/transform/structure.py
index 7240f5f..ce878b0 100644
--- a/prosemirror/transform/structure.py
+++ b/prosemirror/transform/structure.py
@@ -122,14 +122,17 @@ def can_split(doc, pos, depth=None, types_after=None):
         if node.type.spec.get("isolating"):
             return False
         rest = node.content.cut_by_index(index, node.child_count)
+        if types_after and len(types_after) > i:
+            override_child = types_after[i + 1]
+            rest = rest.replace_child(
+                0, override_child["type"].create(override_child.get("attrs"))
+            )
         after = None
         if types_after and len(types_after) > i:
             after = types_after[i]
         if not after:
             after = node
         if isinstance(after, dict):
-            if after != node:
-                rest = rest.replace_child(0, after["type"].create(after.get("attrs")))
             if not node.can_replace(index + 1, node.child_count) or not after[
                 "type"
             ].valid_content(rest):
diff --git a/prosemirror/transform/transform.py b/prosemirror/transform/transform.py
index 131d03b..ac67a4d 100644
--- a/prosemirror/transform/transform.py
+++ b/prosemirror/transform/transform.py
@@ -1,3 +1,4 @@
+import re
 from typing import Union
 
 from prosemirror.model import Fragment, Mark, MarkType, Node, NodeType, Slice
@@ -156,24 +157,43 @@ def clear_incompatible(self, pos, parent_type, match=None):
         if match is None:
             match = parent_type.content_match
         node = self.doc.node_at(pos)
-        del_steps = []
+        repl_steps = []
         cur = pos + 1
         for i in range(node.child_count):
             child = node.child(i)
             end = cur + child.node_size
             allowed = match.match_type(child.type, child.attrs)
             if not allowed:
-                del_steps.append(ReplaceStep(cur, end, Slice.empty))
+                repl_steps.append(ReplaceStep(cur, end, Slice.empty))
             else:
                 match = allowed
                 for j in range(len(child.marks)):
                     if not parent_type.allows_mark_type(child.marks[j].type):
                         self.step(RemoveMarkStep(cur, end, child.marks[j]))
+                if child.is_text and not parent_type.spec.get("code"):
+                    newline = re.compile(r"\r?\n|\r")
+                    slice = None
+                    m = newline.search(child.text)
+                    while m:
+                        if slice is None:
+                            slice = Slice(
+                                Fragment.from_(
+                                    parent_type.schema.text(
+                                        " ", parent_type.allowed_marks(child.marks)
+                                    )
+                                ),
+                                0,
+                                0,
+                            )
+                        repl_steps.append(
+                            ReplaceStep(cur + m.start(), cur + m.end(), slice)
+                        )
+                        m = newline.search(child.text, m.end())
             cur = end
         if not match.valid_end:
             fill = match.fill_before(Fragment.empty, True)
             self.replace(cur, cur, Slice(fill, 0, 0))
-        for item in reversed(del_steps):
+        for item in reversed(repl_steps):
             self.step(item)
         return self
 
@@ -240,11 +260,13 @@ def replace_range(self, from_, to, slice):
 
         d = preferred_depth - 1
         while d >= 0:
-            type = left_nodes[d].type
-            def_ = defines_content(type)
-            if def_ and from__.node(preferred_target_index).type.name != type.name:
+            left_node = left_nodes[d]
+            def_ = defines_content(left_node.type)
+            if def_ and not left_node.same_markup(
+                from__.node(abs(preferred_target) - 1)
+            ):
                 preferred_depth = d
-            elif def_ or not type.is_text_block:
+            elif def_ or not left_node.type.is_text_block:
                 break
             d -= 1
 
diff --git a/tests/prosemirror_transform/tests/test_trans.py b/tests/prosemirror_transform/tests/test_trans.py
index 573a3d8..a1cf79c 100644
--- a/tests/prosemirror_transform/tests/test_trans.py
+++ b/tests/prosemirror_transform/tests/test_trans.py
@@ -502,6 +502,18 @@ def test_wrap(doc, expect, type, attrs, test_transform):
             "code_block",
             None,
         ),
+        (
+            doc(p("<a>one", img(), "two", img(), "three")),
+            doc(pre("onetwothree")),
+            "code_block",
+            None,
+        ),
+        (
+            doc(pre("<a>one\ntwo\nthree")),
+            doc(p("one two three")),
+            "paragraph",
+            None,
+        ),
     ],
 )
 def test_set_block_type(doc, expect, node_type, attrs, test_transform):
@@ -718,6 +730,16 @@ def test_set_node_attribute(doc, expect, attr, value, test_transform):
             doc(blockquote(blockquote(blockquote(p("hi"))))).slice(3, 6, True),
             doc(p("hi")),
         ),
+        (
+            doc(ul(li(p("list1"), blockquote(p("<a>"))))),
+            doc(blockquote(p("<a>one<b>"))),
+            doc(ul(li(p("list1"), blockquote(p("one"))))),
+        ),
+        (
+            doc(ul(li(p("list1"), ul(li(p("list2"), blockquote(p("<a>"))))))),
+            doc(blockquote(p("<a>one<b>"))),
+            doc(ul(li(p("list1"), ul(li(p("list2"), blockquote(p("one"))))))),
+        ),
     ],
 )
 def test_replace(doc, source, expect, test_transform):