sigmavirus24: You're right. This method, at this point in time is not going to be correct or conducive to the right behaviour for the future of the library. Here's what I think we should do:

1. Deprecate `Issue.assign`. It only accepts 1 user and that is outdated and likely going to be confusing going forward.

1. Add `add_assignees` (or something along those lines) that does the right thing (accepts a list of usernames/User objects) and calls `edit` appropriately.

1. Add `remove_assignees` which is the inverse of `add_assignees`.

Does that make sense?
jacquerie: > Does that make sense?

Absolutely! I just pushed three commits that implement the three steps that you described.
diff --git a/src/github3/issues/issue.py b/src/github3/issues/issue.py
index 15b7632a..cdf673fc 100644
--- a/src/github3/issues/issue.py
+++ b/src/github3/issues/issue.py
@@ -2,6 +2,7 @@
 """Module containing the Issue logic."""
 from __future__ import unicode_literals
 
+import warnings
 from json import dumps
 
 from uritemplate import URITemplate
@@ -67,6 +68,27 @@ class _Issue(models.GitHubCore):
             n=self.number, class_name=self.class_name,
         )
 
+    @requires_auth
+    def add_assignees(self, users):
+        """Assign ``users`` to this issue.
+
+        This is a shortcut for :meth:`~github3.issues.issue.Issue.edit`.
+
+        :param users:
+            users or usernames to assign this issue to
+        :type users:
+            list of :class:`~github3.users.User`
+        :type users:
+            list of str
+        :returns:
+            True if successful, False otherwise
+        :rtype:
+            bool
+        """
+        usernames = {getattr(user, 'login', user) for user in users}
+        assignees = list({a.login for a in self.assignees} | usernames)
+        return self.edit(assignees=assignees)
+
     @requires_auth
     def add_labels(self, *args):
         """Add labels to this issue.
@@ -86,6 +108,10 @@ class _Issue(models.GitHubCore):
     def assign(self, username):
         """Assign user ``username`` to this issue.
 
+        .. deprecated:: 1.2.0
+
+            Use :meth:`github3.issues.issue.Issue.add_assignees` instead.
+
         This is a short cut for :meth:`~github3.issues.issue.Issue.edit`.
 
         :param str username:
@@ -95,6 +121,9 @@ class _Issue(models.GitHubCore):
         :rtype:
             bool
         """
+        warnings.warn(
+            'This method is deprecated. Please use ``add_assignees`` '
+            'instead.', DeprecationWarning, stacklevel=2)
         if not username:
             return False
         number = self.milestone.number if self.milestone else None
@@ -300,6 +329,27 @@ class _Issue(models.GitHubCore):
             json = self._json(self._get(pull_request_url), 200)
         return self._instance_or_null(pulls.PullRequest, json)
 
+    @requires_auth
+    def remove_assignees(self, users):
+        """Unassign ``users`` from this issue.
+
+        This is a shortcut for :meth:`~github3.issues.issue.Issue.edit`.
+
+        :param users:
+            users or usernames to unassign this issue from
+        :type users:
+            list of :class:`~github3.users.User`
+        :type users:
+            list of str
+        :returns:
+            True if successful, False otherwise
+        :rtype:
+            bool
+        """
+        usernames = {getattr(user, 'login', user) for user in users}
+        assignees = list({a.login for a in self.assignees} - usernames)
+        return self.edit(assignees=assignees)
+
     @requires_auth
     def remove_label(self, name):
         """Remove label ``name`` from this issue.

No way to unassign an issue
There seems to be an assign function, but not an unassign method for Issue

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new file mode 100644
index 00000000..418ba17b
--- /dev/null
+++ b/tests/cassettes/Issue_add_assignees.json
@@ -0,0 +1,1 @@
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new file mode 100644
index 00000000..2a9ff031
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charset=utf-8"], "X-Accepted-OAuth-Scopes": [""], "X-RateLimit-Reset": ["1533285098"]}, "status": {"message": "OK", "code": 200}, "url": "https://api.github.com/repos/sigmavirus24/github3.py/issues/711"}, "recorded_at": "2018-08-03T08:01:41"}], "recorded_with": "betamax/0.8.1"}
\ No newline at end of file
diff --git a/tests/integration/test_issue.py b/tests/integration/test_issue.py
index d9aadf2e..fc5426ad 100644
--- a/tests/integration/test_issue.py
+++ b/tests/integration/test_issue.py
@@ -11,6 +11,18 @@ class TestIssue(IntegrationHelper):
 
     """Integration tests for methods on the Issue class."""
 
+    def test_add_assignees(self):
+        """Test the ability to add assignees to an issue."""
+        self.auto_login()
+        cassette_name = self.cassette_name('add_assignees')
+        with self.recorder.use_cassette(cassette_name):
+            issue = self.gh.issue(username='sigmavirus24',
+                                  repository='github3.py',
+                                  number=711)
+            assigned = issue.add_assignees(['jacquerie'])
+
+        assert assigned is True
+
     def test_add_labels(self):
         """Test the ability to add a label to an issue."""
         self.auto_login()
@@ -203,6 +215,18 @@ class TestIssue(IntegrationHelper):
 
         assert reopened is True
 
+    def test_remove_assignees(self):
+        """Test the ability to remove assignees from an issue."""
+        self.auto_login()
+        cassette_name = self.cassette_name('remove_assignees')
+        with self.recorder.use_cassette(cassette_name):
+            issue = self.gh.issue(username='sigmavirus24',
+                                  repository='github3.py',
+                                  number=711)
+            unassigned = issue.remove_assignees(['jacquerie'])
+
+        assert unassigned is True
+
     def test_remove_label(self):
         """Test the ability to remove a label from an issue."""
         self.auto_login()
diff --git a/tests/unit/test_issues_issue.py b/tests/unit/test_issues_issue.py
index f8f1f0e0..f67cca29 100644
--- a/tests/unit/test_issues_issue.py
+++ b/tests/unit/test_issues_issue.py
@@ -44,6 +44,10 @@ class TestIssueRequiresAuth(helper.UnitRequiresAuthenticationHelper):
     def after_setup(self):
         self.session.has_auth.return_value = False
 
+    def test_add_assignees(self):
+        """Verify that adding assignees requires authentication."""
+        self.assert_requires_auth(self.instance.add_assignees)
+
     def test_add_labels(self):
         """Verify that adding a label requires authentication."""
         self.assert_requires_auth(self.instance.add_labels, 'enhancement')
@@ -73,6 +77,10 @@ class TestIssueRequiresAuth(helper.UnitRequiresAuthenticationHelper):
         """Verify that removing all labels requires authentication."""
         self.assert_requires_auth(self.instance.remove_all_labels)
 
+    def test_remove_assignees(self):
+        """Verify that removing assignees requires authentication."""
+        self.assert_requires_auth(self.instance.remove_assignees)
+
     def test_remove_label(self):
         """Verify that removing a label requires authentication."""
         self.assert_requires_auth(self.instance.remove_label, 'enhancement')
@@ -92,6 +100,15 @@ class TestIssue(helper.UnitHelper):
     described_class = github3.issues.Issue
     example_data = get_issue_example_data()
 
+    def test_add_assignees(self):
+        """Verify the request for adding assignees to an issue."""
+        self.instance.add_assignees(['jacquerie'])
+
+        self.session.patch.assert_called_with(
+            url_for(),
+            data='{"assignees": ["jacquerie"]}'
+        )
+
     def test_add_labels(self):
         """Verify the request for adding a label."""
         self.instance.add_labels('enhancement')
@@ -294,6 +311,15 @@ class TestIssue(helper.UnitHelper):
             assert self.instance.remove_all_labels() == []
             replace_labels.assert_called_once_with([])
 
+    def test_remove_assignees(self):
+        """Verify the request for removing assignees from an issue."""
+        self.instance.remove_assignees(['octocat'])
+
+        self.session.patch.assert_called_once_with(
+            url_for(),
+            data='{"assignees": []}'
+        )
+
     def test_remove_label(self):
         """Verify the request for removing a label from an issue."""
         self.instance.remove_label('enhancement')

pip install -e .[test]
parse_log_pytest
requirements.txt
pytest pytest-xdist betamax betamax_matchers
apt-get update apt-get install -y gcc
3.6
dev-requirements.txt
pytest --no-header -rA --tb=line --color=no -p no:cacheprovider -W ignore::DeprecationWarning
attrs==22.2.0
betamax==0.8.1
betamax-matchers==0.4.0
certifi==2021.5.30
charset-normalizer==2.0.12
distlib==0.3.9
execnet==1.9.0
filelock==3.4.1
-e git+https://github.com/sigmavirus24/github3.py.git@87af5a1d26597d7cf1a843199a1b5a2449cd8069#egg=github3.py
idna==3.10
importlib-metadata==4.8.3
importlib-resources==5.4.0
iniconfig==1.1.1
mock==1.0.1
packaging==21.3
platformdirs==2.4.0
pluggy==1.0.0
py==1.11.0
pyparsing==3.1.4
pytest==7.0.1
pytest-xdist==3.0.2
python-dateutil==2.9.0.post0
requests==2.27.1
requests-toolbelt==1.0.0
six==1.17.0
swebench-matterhorn @ file:///swebench_matterhorn
toml==0.10.2
tomli==1.2.3
tox==3.28.0
typing_extensions==4.1.1
uritemplate==4.1.1
urllib3==1.26.20
virtualenv==20.17.1
zipp==3.6.0

name: github3.py
channels:
  - defaults
  - https://repo.anaconda.com/pkgs/main
  - https://repo.anaconda.com/pkgs/r
  - conda-forge
dependencies:
  - _libgcc_mutex=0.1=main
  - _openmp_mutex=5.1=1_gnu
  - ca-certificates=2025.2.25=h06a4308_0
  - certifi=2021.5.30=py36h06a4308_0
  - ld_impl_linux-64=2.40=h12ee557_0
  - libffi=3.3=he6710b0_2
  - libgcc-ng=11.2.0=h1234567_1
  - libgomp=11.2.0=h1234567_1
  - libstdcxx-ng=11.2.0=h1234567_1
  - ncurses=6.4=h6a678d5_0
  - openssl=1.1.1w=h7f8727e_0
  - pip=21.2.2=py36h06a4308_0
  - python=3.6.13=h12debd9_1
  - readline=8.2=h5eee18b_0
  - setuptools=58.0.4=py36h06a4308_0
  - sqlite=3.45.3=h5eee18b_0
  - tk=8.6.14=h39e8969_0
  - xz=5.6.4=h5eee18b_1
  - zlib=1.2.13=h5eee18b_1
  - pip:
      - attrs==22.2.0
      - betamax==0.8.1
      - betamax-matchers==0.4.0
      - charset-normalizer==2.0.12
      - distlib==0.3.9
      - execnet==1.9.0
      - filelock==3.4.1
      - idna==3.10
      - importlib-metadata==4.8.3
      - importlib-resources==5.4.0
      - iniconfig==1.1.1
      - mock==1.0.1
      - packaging==21.3
      - platformdirs==2.4.0
      - pluggy==1.0.0
      - py==1.11.0
      - pyparsing==3.1.4
      - pytest==7.0.1
      - pytest-xdist==3.0.2
      - python-dateutil==2.9.0.post0
      - requests==2.27.1
      - requests-toolbelt==1.0.0
      - six==1.17.0
      - swebench-matterhorn==0.0.0
      - toml==0.10.2
      - tomli==1.2.3
      - tox==3.28.0
      - typing-extensions==4.1.1
      - uritemplate==4.1.1
      - urllib3==1.26.20
      - virtualenv==20.17.1
      - wheel==0.21.0
      - zipp==3.6.0
prefix: /opt/conda/envs/github3.py

tests/integration/test_issue.py::TestIssue::test_add_assignees tests/integration/test_issue.py::TestIssue::test_remove_assignees tests/unit/test_issues_issue.py::TestIssueRequiresAuth::test_add_assignees tests/unit/test_issues_issue.py::TestIssueRequiresAuth::test_remove_assignees tests/unit/test_issues_issue.py::TestIssue::test_add_assignees tests/unit/test_issues_issue.py::TestIssue::test_remove_assignees
tests/integration/test_issue.py::TestIssue::test_add_labels tests/integration/test_issue.py::TestIssue::test_assign tests/integration/test_issue.py::TestIssue::test_closed tests/integration/test_issue.py::TestIssue::test_comment tests/integration/test_issue.py::TestIssue::test_comments tests/integration/test_issue.py::TestIssue::test_create_comment tests/integration/test_issue.py::TestIssue::test_edit tests/integration/test_issue.py::TestIssue::test_edit_both_assignee_and_assignees tests/integration/test_issue.py::TestIssue::test_edit_multiple_assignees tests/integration/test_issue.py::TestIssue::test_events tests/integration/test_issue.py::TestIssue::test_labels tests/integration/test_issue.py::TestIssue::test_lock tests/integration/test_issue.py::TestIssue::test_pull_request tests/integration/test_issue.py::TestIssue::test_remove_all_labels tests/integration/test_issue.py::TestIssue::test_remove_label tests/integration/test_issue.py::TestIssue::test_reopen tests/integration/test_issue.py::TestIssue::test_replace_labels tests/integration/test_issue.py::TestIssue::test_unlock tests/integration/test_issue.py::TestLabel::test_delete tests/integration/test_issue.py::TestLabel::test_update tests/unit/test_issues_issue.py::TestIssueRequiresAuth::test_add_labels tests/unit/test_issues_issue.py::TestIssueRequiresAuth::test_assign tests/unit/test_issues_issue.py::TestIssueRequiresAuth::test_close tests/unit/test_issues_issue.py::TestIssueRequiresAuth::test_create_comment tests/unit/test_issues_issue.py::TestIssueRequiresAuth::test_edit_comment tests/unit/test_issues_issue.py::TestIssueRequiresAuth::test_lock tests/unit/test_issues_issue.py::TestIssueRequiresAuth::test_remove_all_labels tests/unit/test_issues_issue.py::TestIssueRequiresAuth::test_remove_label tests/unit/test_issues_issue.py::TestIssueRequiresAuth::test_reopen tests/unit/test_issues_issue.py::TestIssueRequiresAuth::test_unlock tests/unit/test_issues_issue.py::TestIssue::test_add_labels tests/unit/test_issues_issue.py::TestIssue::test_assign tests/unit/test_issues_issue.py::TestIssue::test_assign_empty_username tests/unit/test_issues_issue.py::TestIssue::test_close tests/unit/test_issues_issue.py::TestIssue::test_close_with_unicode_labels tests/unit/test_issues_issue.py::TestIssue::test_comment tests/unit/test_issues_issue.py::TestIssue::test_comment_positive_id tests/unit/test_issues_issue.py::TestIssue::test_create_comment tests/unit/test_issues_issue.py::TestIssue::test_create_comment_required_body tests/unit/test_issues_issue.py::TestIssue::test_create_lock tests/unit/test_issues_issue.py::TestIssue::test_edit tests/unit/test_issues_issue.py::TestIssue::test_edit_milestone tests/unit/test_issues_issue.py::TestIssue::test_edit_multiple_assignees tests/unit/test_issues_issue.py::TestIssue::test_edit_no_parameters tests/unit/test_issues_issue.py::TestIssue::test_enterprise tests/unit/test_issues_issue.py::TestIssue::test_equality tests/unit/test_issues_issue.py::TestIssue::test_is_closed tests/unit/test_issues_issue.py::TestIssue::test_issue_137 tests/unit/test_issues_issue.py::TestIssue::test_pull_request tests/unit/test_issues_issue.py::TestIssue::test_pull_request_without_urls tests/unit/test_issues_issue.py::TestIssue::test_remove_all_labels tests/unit/test_issues_issue.py::TestIssue::test_remove_label tests/unit/test_issues_issue.py::TestIssue::test_remove_lock tests/unit/test_issues_issue.py::TestIssue::test_reopen tests/unit/test_issues_issue.py::TestIssue::test_replace_labels tests/unit/test_issues_issue.py::TestIssueIterators::test_comments tests/unit/test_issues_issue.py::TestIssueIterators::test_events tests/unit/test_issues_issue.py::TestIssueIterators::test_labels tests/unit/test_issues_issue.py::TestLabelRequiresAuth::test_delete tests/unit/test_issues_issue.py::TestLabelRequiresAuth::test_update tests/unit/test_issues_issue.py::TestLabel::test_delete tests/unit/test_issues_issue.py::TestLabel::test_equality tests/unit/test_issues_issue.py::TestLabel::test_repr tests/unit/test_issues_issue.py::TestLabel::test_str tests/unit/test_issues_issue.py::TestLabel::test_update tests/unit/test_issues_issue.py::TestLabel::test_update_without_description tests/unit/test_issues_issue.py::TestIssueEvent::test_assignee tests/unit/test_issues_issue.py::TestIssueEvent::test_created_at tests/unit/test_issues_issue.py::TestIssueEvent::test_equality tests/unit/test_issues_issue.py::TestIssueEvent::test_repr
src/github3/issues/issue.py
src/github3/issues/issue.py