diff --git a/src/application.py b/src/application.py
index 1c7d642..2f879fc 100644
--- a/src/application.py
+++ b/src/application.py
@@ -737,13 +737,6 @@ def create_problem():
         flash('A problem with this name or ID already exists', 'danger')
         return render_template("problem/create.html"), 409
 
-    # Check if file exists & upload if it does
-    file = request.files["file"]
-    if file.filename:
-        filename = problem_id + ".zip"
-        file.save("dl/" + filename)
-        description += f'\n\n[{filename}](/dl/{filename})'
-
     # Modify problems table
     db.execute(("INSERT INTO problems (id, name, point_value, category, flag, draft, "
                 "flag_hint, instanced) VALUES (:id, :name, :point_value, :category, "
@@ -751,6 +744,13 @@ def create_problem():
                id=problem_id, name=name, point_value=point_value, category=category,
                flag=flag, draft=draft, fhint=flag_hint, inst=instanced)
 
+    # Check if file exists & upload if it does
+    file = request.files["file"]
+    if file.filename:
+        filename = problem_id + ".zip"
+        file.save("dl/" + filename)
+        description += f'\n\n[{filename}](/dl/{filename})'
+
     os.makedirs('metadata/problems/' + problem_id)
     write_file('metadata/problems/' + problem_id + '/description.md', description)
     write_file('metadata/problems/' + problem_id + '/hints.md', hints)
diff --git a/src/templates/contest/edit_problem.html b/src/templates/contest/edit_problem.html
index 54c76f4..c687302 100644
--- a/src/templates/contest/edit_problem.html
+++ b/src/templates/contest/edit_problem.html
@@ -9,7 +9,7 @@
 
 {% block main %}
 <h1>Edit {{ data["name"] }}</h1>
-<form autocomplete="off" method="post">
+<form autocomplete="off" method="post" enctype="multipart/form-data">
      <div class="form-floating">
         <input class="form-control mb-3"
                name="name"
@@ -80,6 +80,10 @@ <h1>Edit {{ data["name"] }}</h1>
                required>
         <label for="point_value">Point Value</label>
     </div>
+    <div class="input-group mb-3">
+        <label class="input-group-text" for="file">New File (optional)</label>
+        <input class="form-control" type="file" id="file" name="file" accept=".zip">
+    </div>
     <input class="btn btn-primary" type="submit" id="submit" name="submit" value="Submit">
     <input type="hidden" name="csrf_token" value="{{ csrf_token() }}"/>
 </form>
diff --git a/src/templates/problem/edit_problem.html b/src/templates/problem/edit_problem.html
index d50b165..39bc5c7 100644
--- a/src/templates/problem/edit_problem.html
+++ b/src/templates/problem/edit_problem.html
@@ -9,7 +9,7 @@
 
 {% block main %}
 <h1>Edit {{ data["name"] }}</h1>
-<form autocomplete="off" method="post">
+<form autocomplete="off" method="post" enctype="multipart/form-data">
     <div class="form-floating">
         <input class="form-control mb-3"
                name="name"
@@ -79,6 +79,10 @@ <h1>Edit {{ data["name"] }}</h1>
                required>
         <label for="point_value">Point Value</label>
     </div>
+    <div class="input-group mb-3">
+        <label class="input-group-text" for="file">New File (optional)</label>
+        <input class="form-control" type="file" id="file" name="file" accept=".zip">
+    </div>
     <input class="btn btn-primary" type="submit" id="submit" name="submit" value="Submit">
     <input type="hidden" name="csrf_token" value="{{ csrf_token() }}"/>
 </form>
diff --git a/src/tests/conftest.py b/src/tests/conftest.py
index 154a076..e0a773e 100644
--- a/src/tests/conftest.py
+++ b/src/tests/conftest.py
@@ -23,6 +23,7 @@ def client():
     app.config['USE_CAPTCHA'] = False
     app.config['WTF_CSRF_ENABLED'] = False
     app.config['SECRET_KEY'] = 'testing_secret_key'
+    open('fake_empty_file', 'w').close()
     return app.test_client()
 
 
diff --git a/src/tests/test_contest.py b/src/tests/test_contest.py
index 28d5e56..7419833 100644
--- a/src/tests/test_contest.py
+++ b/src/tests/test_contest.py
@@ -121,6 +121,7 @@ def test_contest(client, database):
         'hints': 'try looking at the title 2',
         'point_value': 2,
         'category': 'web',
+        'file': ('fake_empty_file', ''),
         'instanced': True,
     })
     assert result.status_code == 302
@@ -281,7 +282,8 @@ def test_contest(client, database):
         'name': 'dynscore',
         'description': 'dynamic is fun',
         'category': 'web',
-        'flag': 'ctf{nobodywillguessme}'
+        'flag': 'ctf{nobodywillguessme}',
+        'file': ('fake_empty_file', ''),
     })
     assert result.status_code == 302
 
@@ -293,7 +295,8 @@ def test_contest(client, database):
         'description': 'dynamic is fun',
         'category': 'web',
         'flag': 'ctf{nobodywillguessmeagain}',
-        'rejudge': True
+        'rejudge': True,
+        'file': ('fake_empty_file', ''),
     })
     assert result.status_code == 302
 
diff --git a/src/tests/test_problems.py b/src/tests/test_problems.py
index f4ac5e5..6aab635 100644
--- a/src/tests/test_problems.py
+++ b/src/tests/test_problems.py
@@ -61,7 +61,8 @@ def test_problem(client, database):
         'point_value': 2,
         'rejudge': True,
         'category': 'web',
-        'flag': 'ctf{hello}'
+        'flag': 'ctf{hello}',
+        'file': ('fake_empty_file', ''),
     })
     assert result.status_code == 400
     assert b'required' in result.data
@@ -73,11 +74,15 @@ def test_problem(client, database):
         'point_value': 2,
         'rejudge': True,
         'category': 'web',
-        'flag': '\x2f\x10'
+        'flag': '\x2f\x10',
+        'file': ('fake_empty_file', ''),
     })
     assert result.status_code == 400
     assert b'Invalid' in result.data
 
+    file = open("test_upload.txt", "w")
+    file.write('ree2')
+    file.close()
     result = client.post('/problem/helloworldtesting/edit', data={
         'name': 'hello world 2',
         'description': 'a short fun problem 2',
@@ -86,10 +91,14 @@ def test_problem(client, database):
         'rejudge': True,
         'category': 'web',
         'flag': 'ctf{hello}',
-        'flag_hint': 'ctf{...}'
+        'flag_hint': 'ctf{...}',
+        'file': ('test_upload.txt', 'test_upload.txt'),
     }, follow_redirects=True)
     assert result.status_code == 200
 
+    result = client.get('/dl/helloworldtesting.zip')
+    assert result.data == b'ree2'
+
     result = client.get('/users/admin/profile')
     assert result.status_code == 200
     assert b'2 Points' in result.data
@@ -112,7 +121,7 @@ def test_problem(client, database):
 
     result = client.get('/api/problem?id=helloworldtesting')
     assert json.loads(result.data)['status'] == 'success'
-    assert json.loads(result.data)['data']['description'] == 'a short fun problem 2'
+    assert json.loads(result.data)['data']['description'].startswith('a short fun problem 2')
     assert json.loads(result.data)['data']['hints'] == 'try looking at the title 2'
     assert json.loads(result.data)['data']['editorial'] == 'sample editorial'
     assert json.loads(result.data)['data']['flag_hint'] == 'ctf{...}'
diff --git a/src/views/contest.py b/src/views/contest.py
index e527a86..5de339f 100644
--- a/src/views/contest.py
+++ b/src/views/contest.py
@@ -315,6 +315,7 @@ def publish_contest_problem(contest_id, problem_id):
 @api.route('/<contest_id>/problem/<problem_id>/edit', methods=["GET", "POST"])
 @admin_required
 def edit_contest_problem(contest_id, problem_id):
+
     # Ensure contest exists
     if not contest_exists(contest_id):
         return render_template("contest/contest_noexist.html"), 404
@@ -376,7 +377,16 @@ def edit_contest_problem(contest_id, problem_id):
                 "flag_hint=:fhint, instanced=:inst WHERE contest_id=:cid AND problem_id=:pid"),
                name=new_name, category=new_category, flag=new_flag, cid=contest_id,
                pid=problem_id, fhint=new_flag_hint, inst=new_instanced)
-
+    # Check if file exists & upload if it does
+    file = request.files["file"]
+    if file.filename:
+        if not os.path.exists("dl/" + contest_id):
+            os.makedirs("dl/" + contest_id)
+        filename = problem_id + ".zip"
+        filepath = "dl/" + contest_id + "/"
+        file.save(filepath + filename)
+        if f'[{filename}](/{filepath + filename})' not in new_description:
+            new_description += f'\n\n[{filename}](/{filepath + filename})'
     write_file(
         f'metadata/contests/{contest_id}/{problem_id}/description.md', new_description)
     write_file(f'metadata/contests/{contest_id}/{problem_id}/hints.md', new_hint)
diff --git a/src/views/problem.py b/src/views/problem.py
index a6d08df..59d661c 100644
--- a/src/views/problem.py
+++ b/src/views/problem.py
@@ -178,6 +178,15 @@ def editproblem(problem_id):
          "(SELECT user_id FROM problem_solved WHERE problem_id=:pid)"),
         dpv=new_points - data[0]["point_value"], pid=problem_id
     )
+
+    # Check if file exists & upload if it does
+    file = request.files["file"]
+    if file.filename:
+        filename = problem_id + ".zip"
+        file.save("dl/" + filename)
+        if f'[{filename}](/dl/{filename})' not in new_description:
+            new_description += f'\n\n[{filename}](/dl/{filename})'
+
     write_file('metadata/problems/' + problem_id + '/description.md', new_description)
     write_file('metadata/problems/' + problem_id + '/hints.md', new_hint)