diff --git a/src/transforms/at-range.js b/src/transforms/at-range.js
index 29b38fca0..a20eb46af 100644
--- a/src/transforms/at-range.js
+++ b/src/transforms/at-range.js
@@ -92,7 +92,8 @@ export function deleteAtRange(transform, range) {
     transform.moveNodeByKey(child.key, newKey, newIndex)
   })
 
-  transform.removeNodeByKey(endChild.key)
+  const lonely = document.getFurthest(endBlock, p => p.nodes.size == 1) || endBlock
+  transform.removeNodeByKey(lonely.key)
   transform.normalizeDocument()
   return transform
 }
diff --git a/test/transforms/fixtures/at-range/delete-at-range/join-across-nested-blocks/index.js b/test/transforms/fixtures/at-range/delete-at-range/join-across-nested-blocks/index.js
new file mode 100644
index 000000000..3e1780eca
--- /dev/null
+++ b/test/transforms/fixtures/at-range/delete-at-range/join-across-nested-blocks/index.js
@@ -0,0 +1,18 @@
+
+export default function (state) {
+  const { document, selection } = state
+  const texts = document.getTexts()
+  const second = texts.get(1)
+  const third = texts.get(2)
+  const range = selection.merge({
+    anchorKey: second.key,
+    anchorOffset: second.length,
+    focusKey: third.key,
+    focusOffset: 0
+  })
+
+  return state
+    .transform()
+    .deleteAtRange(range)
+    .apply()
+}
diff --git a/test/transforms/fixtures/at-range/delete-at-range/join-across-nested-blocks/input.yaml b/test/transforms/fixtures/at-range/delete-at-range/join-across-nested-blocks/input.yaml
new file mode 100644
index 000000000..188259ec6
--- /dev/null
+++ b/test/transforms/fixtures/at-range/delete-at-range/join-across-nested-blocks/input.yaml
@@ -0,0 +1,28 @@
+
+nodes:
+  - kind: block
+    type: list
+    nodes:
+      - kind: block
+        type: item
+        nodes:
+          - kind: text
+            text: one
+      - kind: block
+        type: item
+        nodes:
+          - kind: text
+            text: two
+  - kind: block
+    type: list
+    nodes:
+      - kind: block
+        type: item
+        nodes:
+          - kind: text
+            text: three
+      - kind: block
+        type: item
+        nodes:
+          - kind: text
+            text: four
diff --git a/test/transforms/fixtures/at-range/delete-at-range/join-across-nested-blocks/output.yaml b/test/transforms/fixtures/at-range/delete-at-range/join-across-nested-blocks/output.yaml
new file mode 100644
index 000000000..eb8f589c8
--- /dev/null
+++ b/test/transforms/fixtures/at-range/delete-at-range/join-across-nested-blocks/output.yaml
@@ -0,0 +1,23 @@
+
+nodes:
+  - kind: block
+    type: list
+    nodes:
+      - kind: block
+        type: item
+        nodes:
+          - kind: text
+            text: one
+      - kind: block
+        type: item
+        nodes:
+          - kind: text
+            text: twothree
+  - kind: block
+    type: list
+    nodes:
+      - kind: block
+        type: item
+        nodes:
+          - kind: text
+            text: four
diff --git a/test/transforms/fixtures/at-range/delete-at-range/across-nested-blocks/index.js b/test/transforms/fixtures/at-range/delete-at-range/join-nested-blocks/index.js
similarity index 100%
rename from test/transforms/fixtures/at-range/delete-at-range/across-nested-blocks/index.js
rename to test/transforms/fixtures/at-range/delete-at-range/join-nested-blocks/index.js
diff --git a/test/transforms/fixtures/at-range/delete-at-range/across-nested-blocks/input.yaml b/test/transforms/fixtures/at-range/delete-at-range/join-nested-blocks/input.yaml
similarity index 100%
rename from test/transforms/fixtures/at-range/delete-at-range/across-nested-blocks/input.yaml
rename to test/transforms/fixtures/at-range/delete-at-range/join-nested-blocks/input.yaml
diff --git a/test/transforms/fixtures/at-range/delete-at-range/across-nested-blocks/output.yaml b/test/transforms/fixtures/at-range/delete-at-range/join-nested-blocks/output.yaml
similarity index 100%
rename from test/transforms/fixtures/at-range/delete-at-range/across-nested-blocks/output.yaml
rename to test/transforms/fixtures/at-range/delete-at-range/join-nested-blocks/output.yaml