diff --git a/freqtrade/freqtradebot.py b/freqtrade/freqtradebot.py
index d62c6a912..e2d4454ef 100644
--- a/freqtrade/freqtradebot.py
+++ b/freqtrade/freqtradebot.py
@@ -705,7 +705,7 @@ class FreqtradeBot:
         if trade.stop_loss > float(order['info']['stopPrice']):
             # we check if the update is neccesary
             update_beat = self.strategy.order_types.get('stoploss_on_exchange_interval', 60)
-            if (datetime.utcnow() - trade.stoploss_last_update).total_seconds() > update_beat:
+            if (datetime.utcnow() - trade.stoploss_last_update).total_seconds() >= update_beat:
                 # cancelling the current stoploss on exchange first
                 logger.info('Trailing stoploss: cancelling current stoploss on exchange (id:{%s})'
                             'in order to add another one ...', order['id'])
diff --git a/tests/strategy/test_strategy.py b/tests/strategy/test_strategy.py
index 52216e0ef..12770f2c7 100644
--- a/tests/strategy/test_strategy.py
+++ b/tests/strategy/test_strategy.py
@@ -1,6 +1,5 @@
 # pragma pylint: disable=missing-docstring, protected-access, C0103
 import logging
-import tempfile
 import warnings
 from base64 import urlsafe_b64encode
 from os import path
@@ -51,7 +50,7 @@ def test_load_strategy_base64(result, caplog, default_conf):
     assert 'rsi' in resolver.strategy.advise_indicators(result, {'pair': 'ETH/BTC'})
     # Make sure strategy was loaded from base64 (using temp directory)!!
     assert log_has_re(r"Using resolved strategy SampleStrategy from '"
-                      + tempfile.gettempdir() + r"/.*/SampleStrategy\.py'\.\.\.", caplog)
+                      r".*(/|\\).*(/|\\)SampleStrategy\.py'\.\.\.", caplog)
 
 
 def test_load_strategy_invalid_directory(result, caplog, default_conf):
diff --git a/tests/test_configuration.py b/tests/test_configuration.py
index b133c3609..2aa805fe6 100644
--- a/tests/test_configuration.py
+++ b/tests/test_configuration.py
@@ -399,7 +399,7 @@ def test_setup_configuration_with_arguments(mocker, default_conf, caplog) -> Non
     assert 'pair_whitelist' in config['exchange']
     assert 'datadir' in config
     assert log_has('Using data directory: {} ...'.format("/foo/bar"), caplog)
-    assert log_has('Using user-data directory: {} ...'.format("/tmp/freqtrade"), caplog)
+    assert log_has('Using user-data directory: {} ...'.format(Path("/tmp/freqtrade")), caplog)
     assert 'user_data_dir' in config
 
     assert 'ticker_interval' in config
@@ -652,9 +652,9 @@ def test_create_userdata_dir(mocker, default_conf, caplog) -> None:
     x = create_userdata_dir('/tmp/bar', create_dir=True)
     assert md.call_count == 7
     assert md.call_args[1]['parents'] is False
-    assert log_has('Created user-data directory: /tmp/bar', caplog)
+    assert log_has(f'Created user-data directory: {Path("/tmp/bar")}', caplog)
     assert isinstance(x, Path)
-    assert str(x) == "/tmp/bar"
+    assert str(x) == str(Path("/tmp/bar"))
 
 
 def test_create_userdata_dir_exists(mocker, default_conf, caplog) -> None:
@@ -669,7 +669,8 @@ def test_create_userdata_dir_exists_exception(mocker, default_conf, caplog) -> N
     mocker.patch.object(Path, "is_dir", MagicMock(return_value=False))
     md = mocker.patch.object(Path, 'mkdir', MagicMock())
 
-    with pytest.raises(OperationalException, match=r'Directory `/tmp/bar` does not exist.*'):
+    with pytest.raises(OperationalException,
+                       match=r'Directory `.{1,2}tmp.{1,2}bar` does not exist.*'):
         create_userdata_dir('/tmp/bar',  create_dir=False)
     assert md.call_count == 0
 
diff --git a/tests/test_freqtradebot.py b/tests/test_freqtradebot.py
index 7fb84f078..b2268acc5 100644
--- a/tests/test_freqtradebot.py
+++ b/tests/test_freqtradebot.py
@@ -1449,7 +1449,7 @@ def test_tsl_on_exchange_compatible_with_edge(mocker, edge_conf, fee, caplog,
     # setting stoploss
     freqtrade.strategy.stoploss = -0.02
 
-    # setting stoploss_on_exchange_interval to 0 second
+    # setting stoploss_on_exchange_interval to 0 seconds
     freqtrade.strategy.order_types['stoploss_on_exchange_interval'] = 0
 
     patch_get_signal(freqtrade)
diff --git a/tests/test_plotting.py b/tests/test_plotting.py
index 86f5610da..a39b2b76e 100644
--- a/tests/test_plotting.py
+++ b/tests/test_plotting.py
@@ -214,11 +214,12 @@ def test_generate_plot_file(mocker, caplog):
     store_plot_file(fig, filename="freqtrade-plot-UNITTEST_BTC-5m.html",
                     directory=Path("user_data/plots"))
 
+    expected_fn = str(Path("user_data/plots/freqtrade-plot-UNITTEST_BTC-5m.html"))
     assert plot_mock.call_count == 1
     assert plot_mock.call_args[0][0] == fig
     assert (plot_mock.call_args_list[0][1]['filename']
-            == "user_data/plots/freqtrade-plot-UNITTEST_BTC-5m.html")
-    assert log_has("Stored plot as user_data/plots/freqtrade-plot-UNITTEST_BTC-5m.html",
+            == expected_fn)
+    assert log_has(f"Stored plot as {expected_fn}",
                    caplog)