diff --git a/sandbox/darren/just_a_box.css b/sandbox/darren/just_a_box.css
index 1965ecb95..765fd5651 100644
--- a/sandbox/darren/just_a_box.css
+++ b/sandbox/darren/just_a_box.css
@@ -1,8 +1,3 @@
-Screen {
-    layout: dock;
-    height: 100%;
-}
-
 #box {
     height: 50%;
     width: 50%;
diff --git a/sandbox/darren/just_a_box.py b/sandbox/darren/just_a_box.py
index 2541c7b2b..0750afc43 100644
--- a/sandbox/darren/just_a_box.py
+++ b/sandbox/darren/just_a_box.py
@@ -1,10 +1,27 @@
+from __future__ import annotations
+
+from rich.console import RenderableType
+from rich.panel import Panel
+
 from textual.app import App, ComposeResult
-from textual.widgets import Static
+from textual.widget import Widget
+
+
+class Box(Widget):
+    CSS = "#box {background: blue;}"
+
+    def __init__(
+        self, id: str | None = None, classes: str | None = None, *children: Widget
+    ):
+        super().__init__(*children, id=id, classes=classes)
+
+    def render(self) -> RenderableType:
+        return Panel("Box")
 
 
 class JustABox(App):
     def compose(self) -> ComposeResult:
-        yield Static("Hello, World!", id="box")
+        yield Box(id="box")
 
 
 if __name__ == "__main__":
diff --git a/src/textual/css/model.py b/src/textual/css/model.py
index 89623ac95..bf4e9e7c8 100644
--- a/src/textual/css/model.py
+++ b/src/textual/css/model.py
@@ -156,6 +156,7 @@ class RuleSet:
     styles: Styles = field(default_factory=Styles)
     errors: list[tuple[Token, str]] = field(default_factory=list)
     classes: set[str] = field(default_factory=set)
+    is_widget_rule_set: bool = False
 
     @classmethod
     def _selector_to_css(cls, selectors: list[Selector]) -> str:
diff --git a/src/textual/css/styles.py b/src/textual/css/styles.py
index 30a2f2234..4530bacd2 100644
--- a/src/textual/css/styles.py
+++ b/src/textual/css/styles.py
@@ -56,6 +56,7 @@ from .types import (
     AlignVertical,
     Visibility,
     ScrollbarGutter,
+    Specificity5,
 )
 
 if sys.version_info >= (3, 8):
@@ -511,20 +512,27 @@ class Styles(StylesBase):
         self._rules.update(rules)
 
     def extract_rules(
-        self, specificity: Specificity3
-    ) -> list[tuple[str, Specificity4, Any]]:
-        """Extract rules from Styles object, and apply !important css specificity.
+        self,
+        specificity: Specificity3,
+        is_widget_rule: bool = False,
+    ) -> list[tuple[str, Specificity5, Any]]:
+        """Extract rules from Styles object, and apply !important css specificity as
+        well as higher specificity of user CSS vs widget CSS.
 
         Args:
             specificity (Specificity3): A node specificity.
 
         Returns:
-            list[tuple[str, Specificity4, Any]]]: A list containing a tuple of <RULE NAME>, <SPECIFICITY> <RULE VALUE>.
+            list[tuple[str, Specificity5, Any]]]: A list containing a tuple of <RULE NAME>, <SPECIFICITY> <RULE VALUE>.
         """
         is_important = self.important.__contains__
 
         rules = [
-            (rule_name, (int(is_important(rule_name)), *specificity), rule_value)
+            (
+                rule_name,
+                (int(not is_widget_rule), int(is_important(rule_name)), *specificity),
+                rule_value,
+            )
             for rule_name, rule_value in self._rules.items()
         ]
 
diff --git a/src/textual/css/stylesheet.py b/src/textual/css/stylesheet.py
index b627a6e8f..bc2f6e61c 100644
--- a/src/textual/css/stylesheet.py
+++ b/src/textual/css/stylesheet.py
@@ -122,6 +122,8 @@ class Stylesheet:
         self._rules: list[RuleSet] = []
         self.variables = variables or {}
         self.source: dict[str, str] = {}
+        # Records which of the source keys represent CSS defined at the widget level
+        self._widget_css_paths: set[str] = set()
         self._require_parse = False
 
     def __rich_repr__(self) -> rich.repr.Result:
@@ -147,6 +149,7 @@ class Stylesheet:
         """
         stylesheet = Stylesheet(variables=self.variables.copy())
         stylesheet.source = self.source.copy()
+        stylesheet._widget_css_paths = self._widget_css_paths.copy()
         return stylesheet
 
     def set_variables(self, variables: dict[str, str]) -> None:
@@ -160,7 +163,6 @@ class Stylesheet:
     def _parse_rules(self, css: str, path: str | PurePath) -> list[RuleSet]:
         """Parse CSS and return rules.
 
-
         Args:
             css (str): String containing Textual CSS.
             path (str | PurePath): Path to CSS or unique identifier
@@ -177,6 +179,11 @@ class Stylesheet:
             raise
         except Exception as error:
             raise StylesheetError(f"failed to parse css; {error}")
+
+        if path in self._widget_css_paths:
+            for rule in rules:
+                rule.is_widget_rule_set = True
+
         return rules
 
     def read(self, filename: str | PurePath) -> None:
@@ -199,13 +206,17 @@ class Stylesheet:
         self.source[str(path)] = css
         self._require_parse = True
 
-    def add_source(self, css: str, path: str | PurePath | None = None) -> None:
+    def add_source(
+        self, css: str, path: str | PurePath | None = None, is_widget_css: bool = False
+    ) -> None:
         """Parse CSS from a string.
 
         Args:
             css (str): String with CSS source.
             path (str | PurePath, optional): The path of the source if a file, or some other identifier.
                 Defaults to None.
+            is_widget_css (bool): True if the CSS is defined in the Widget, False if the CSS is defined
+                in a user stylesheet.
 
         Raises:
             StylesheetError: If the CSS could not be read.
@@ -220,6 +231,11 @@ class Stylesheet:
             # Path already in source, and CSS is identical
             return
 
+        # Record any CSS defined at the widget level for
+        # different specificity treatment from user CSS.
+        if is_widget_css:
+            self._widget_css_paths.add(path)
+
         self.source[path] = css
         self._require_parse = True
 
@@ -286,9 +302,10 @@ class Stylesheet:
 
         # Collect the rules defined in the stylesheet
         for rule in reversed(self.rules):
-            for specificity in _check_rule(rule, node):
+            is_widget_rule = rule.is_widget_rule_set
+            for base_specificity in _check_rule(rule, node):
                 for key, rule_specificity, value in rule.styles.extract_rules(
-                    specificity
+                    base_specificity, is_widget_rule
                 ):
                     rule_attributes[key].append((rule_specificity, value))
 
diff --git a/src/textual/css/types.py b/src/textual/css/types.py
index e7fd749b2..1463bf6fa 100644
--- a/src/textual/css/types.py
+++ b/src/textual/css/types.py
@@ -37,5 +37,7 @@ ScrollbarGutter = Literal["auto", "stable"]
 BoxSizing = Literal["border-box", "content-box"]
 Overflow = Literal["scroll", "hidden", "auto"]
 EdgeStyle = Tuple[EdgeType, Color]
+
 Specificity3 = Tuple[int, int, int]
 Specificity4 = Tuple[int, int, int, int]
+Specificity5 = Tuple[int, int, int, int, int]
diff --git a/src/textual/widget.py b/src/textual/widget.py
index 2100f70fd..11d79780c 100644
--- a/src/textual/widget.py
+++ b/src/textual/widget.py
@@ -74,12 +74,12 @@ class Widget(DOMNode):
     CSS = """
     Widget{
         scrollbar-background: $panel-darken-2;
-        scrollbar-background-hover: $panel-darken-3;        
+        scrollbar-background-hover: $panel-darken-3;
         scrollbar-color: $system;
-        scrollbar-color-active: $secondary-darken-1;                
+        scrollbar-color-active: $secondary-darken-1;
         scrollbar-size-vertical: 2;
         scrollbar-size-horizontal: 1;
-        
+
     }
     """
 
@@ -194,7 +194,7 @@ class Widget(DOMNode):
         """
         # Parse the Widget's CSS
         for path, css in self.css:
-            self.app.stylesheet.add_source(css, path=path)
+            self.app.stylesheet.add_source(css, path=path, is_widget_css=True)
 
     def get_box_model(
         self, container: Size, viewport: Size, fraction_unit: Fraction
diff --git a/tests/css/test_stylesheet.py b/tests/css/test_stylesheet.py
index 1727b2911..fd98e8904 100644
--- a/tests/css/test_stylesheet.py
+++ b/tests/css/test_stylesheet.py
@@ -104,22 +104,25 @@ def test_stylesheet_apply_empty_rulesets():
     stylesheet.apply(node)
 
 
-@pytest.mark.xfail(reason="wip")
 def test_stylesheet_apply_user_css_over_widget_css():
-    user_css = ".a {color: red;}"
+    user_css = ".a {color: red; tint: yellow;}"
 
     class MyWidget(Widget):
-        CSS = ".a {color: blue;}"
+        CSS = ".a {color: blue; background: lime;}"
 
     node = MyWidget()
     node.add_class("a")
 
-    print(node.styles.color)
     stylesheet = _make_stylesheet(user_css)
+    stylesheet.add_source(MyWidget.CSS, "widget.py:MyWidget", is_widget_css=True)
     stylesheet.apply(node)
 
-    assert node.styles.background == Color(0, 0, 255)
-    # TODO: On Tuesday - writing the tests for prioritising user CSS above widget CSS.
+    # The node is red because user CSS overrides Widget.CSS
+    assert node.styles.color == Color(255, 0, 0)
+    # The background colour defined in the Widget still applies, since user CSS doesn't override it
+    assert node.styles.background == Color(0, 255, 0)
+    # As expected, the tint colour is yellow, since there's no competition between user or widget CSS
+    assert node.styles.tint == Color(255, 255, 0)
 
 
 @pytest.mark.parametrize(