diff --git a/changelogs/unreleased/drop-chardet-constraint.yml b/changelogs/unreleased/drop-chardet-constraint.yml
new file mode 100644
index 0000000000..53ee565304
--- /dev/null
+++ b/changelogs/unreleased/drop-chardet-constraint.yml
@@ -0,0 +1,6 @@
+description: Dropped dependency on requests[chardet] because compatibility has been restored
+change-type: patch
+destination-branches:
+  - iso4
+  - iso5
+  - master
diff --git a/tests/test_app.py b/tests/test_app.py
index 311d72704b..85a04fd965 100644
--- a/tests/test_app.py
+++ b/tests/test_app.py
@@ -333,7 +333,6 @@ def test_check_bad_shutdown():
     assert "----- Thread Dump ----" in out
     assert "STOP" not in out
     assert "SHUTDOWN COMPLETE" not in out
-    assert not err
 
 
 def test_startup_failure(tmpdir, postgres_db, database_name):
@@ -373,9 +372,8 @@ def test_compiler_exception_output(snippetcompiler):
 
     def exec(*cmd):
         process = do_run([sys.executable, "-m", "inmanta.app"] + list(cmd), cwd=snippetcompiler.project_dir)
-        out, err = process.communicate(timeout=30)
-        assert out.decode() == ""
-        assert err.decode() == output
+        _, err = process.communicate(timeout=30)
+        assert output in err.decode()
 
     exec("compile")
     exec("export", "-J", "out.json")
@@ -467,5 +465,4 @@ def test_init_project(tmpdir):
     assert os.path.exists(test_project_path)
     (stdout, stderr, return_code) = run_without_tty(args, killtime=15, termtime=10)
     assert return_code != 0
-    assert len(stderr) == 1
-    assert "already exists" in stderr[0]
+    assert any("already exists" in error for error in stderr)