diff --git a/CHANGELOG.md b/CHANGELOG.md
index 126548ebc..0dc52b1a7 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -3,6 +3,7 @@
 **v5.2.0 (unreleased):**
 
 * Migrate installation of `ottr` from `setup.sh` to `environment.yml` with the [`r-ottr` conda-forge recipe](https://anaconda.org/conda-forge/r-ottr)
+* Updated Otter Assign to allow multiline statements in test cases per [#590](https://github.com/ucbds-infra/otter-grader/issues/590)
 
 **v5.1.2:**
 
diff --git a/otter/assign/utils.py b/otter/assign/utils.py
index 453ff91a5..bbedbf79c 100644
--- a/otter/assign/utils.py
+++ b/otter/assign/utils.py
@@ -160,7 +160,7 @@ def remove_tag(cell, tag):
     return cell
 
 
-def str_to_doctest(code_lines, lines):
+def str_to_doctest(code_lines, lines, opens=None):
     """
     Convert a list of lines of Python code ``code_lines`` to the doctest format and appending the
     results to ``lines``.
@@ -174,16 +174,26 @@ def str_to_doctest(code_lines, lines):
     """
     if len(code_lines) == 0:
         return lines
+    if opens is None:
+        opens = []
+    in_statement = len(opens) > 0
     line = code_lines.pop(0)
+    for c in line:
+        if c == "(" or c == "[" or c == "{":
+            opens.append(c)
+        elif c == ")" or c == "]" or c == "}":
+            opens.pop()
     if line.startswith(" ") or line.startswith("\t"):
-        return str_to_doctest(code_lines, lines + ["... " + line])
+        return str_to_doctest(code_lines, lines + ["... " + line], opens=opens)
     elif bool(re.match(r"^except[\s\w]*:", line)) or line.startswith("elif ") or \
             line.startswith("else:") or line.startswith("finally:"):
-        return str_to_doctest(code_lines, lines + ["... " + line])
+        return str_to_doctest(code_lines, lines + ["... " + line], opens=opens)
     elif len(lines) > 0 and lines[-1].strip().endswith("\\"):
-        return str_to_doctest(code_lines, lines + ["... " + line])
+        return str_to_doctest(code_lines, lines + ["... " + line], opens=opens)
+    elif in_statement:
+        return str_to_doctest(code_lines, lines + ["... " + line], opens=opens)
     else:
-        return str_to_doctest(code_lines, lines + [">>> " + line])
+        return str_to_doctest(code_lines, lines + [">>> " + line], opens=opens)
 
 
 def run_tests(assignment, debug=False):
diff --git a/test/test_assign/files/example-autograder-correct/tests/q1.py b/test/test_assign/files/example-autograder-correct/tests/q1.py
index 9f1dab417..228572c48 100644
--- a/test/test_assign/files/example-autograder-correct/tests/q1.py
+++ b/test/test_assign/files/example-autograder-correct/tests/q1.py
@@ -2,7 +2,7 @@
 
 test = {   'name': 'q1',
     'points': None,
-    'suites': [   {   'cases': [   {   'code': '>>> isinstance(x, int)\nTrue',
+    'suites': [   {   'cases': [   {   'code': '>>> isinstance(    x,\n...     int,\n... )\nTrue',
                                        'failure_message': 'This is not an int.',
                                        'hidden': False,
                                        'locked': False,
diff --git a/test/test_assign/files/example-correct/autograder/example.ipynb b/test/test_assign/files/example-correct/autograder/example.ipynb
index 9d5ce105c..2bd549c9a 100644
--- a/test/test_assign/files/example-correct/autograder/example.ipynb
+++ b/test/test_assign/files/example-correct/autograder/example.ipynb
@@ -481,7 +481,7 @@
       {
        "cases": [
         {
-         "code": ">>> isinstance(x, int)\nTrue",
+         "code": ">>> isinstance(    x,\n...     int,\n... )\nTrue",
          "failure_message": "This is not an int.",
          "hidden": false,
          "locked": false,
diff --git a/test/test_assign/files/example-correct/student/example.ipynb b/test/test_assign/files/example-correct/student/example.ipynb
index c1da8d382..5c4874b9d 100644
--- a/test/test_assign/files/example-correct/student/example.ipynb
+++ b/test/test_assign/files/example-correct/student/example.ipynb
@@ -390,7 +390,7 @@
       {
        "cases": [
         {
-         "code": ">>> isinstance(x, int)\nTrue",
+         "code": ">>> isinstance(    x,\n...     int,\n... )\nTrue",
          "failure_message": "This is not an int.",
          "hidden": false,
          "locked": false,
diff --git a/test/test_assign/files/example.ipynb b/test/test_assign/files/example.ipynb
index ed5c4d447..c840acaa9 100644
--- a/test/test_assign/files/example.ipynb
+++ b/test/test_assign/files/example.ipynb
@@ -99,7 +99,10 @@
     "failure_message: This is not an int.\n",
     "name: q1a-1\n",
     "\"\"\" # END TEST CONFIG\n",
-    "isinstance(x, int)"
+    "isinstance(",
+    "    x,\n",
+    "    int,\n",
+    ")"
    ]
   },
   {
diff --git a/test/utils.py b/test/utils.py
index ef2847d78..e545eeabd 100644
--- a/test/utils.py
+++ b/test/utils.py
@@ -49,7 +49,11 @@ def assert_notebooks_equal(p1, p2):
     # ignore cell IDs
     for c in [*nb1.cells, *nb2.cells]:
         c.pop("id", None)
-    assert nb1 == nb2
+    diff = subprocess.run(
+        ["diff", "--context=5", p1, p2],
+        stdout=subprocess.PIPE,
+    ).stdout.decode("utf-8")
+    assert nb1 == nb2, f"Contents of {p1} did not equal contents of {p2}:\n{diff}"
 
 
 def assert_files_equal(p1, p2, ignore_trailing_whitespace=True):