diff --git a/playwright/_impl/_assertions.py b/playwright/_impl/_assertions.py
index 163b156ed..13e7ac481 100644
--- a/playwright/_impl/_assertions.py
+++ b/playwright/_impl/_assertions.py
@@ -511,15 +511,14 @@ async def to_be_attached(
         timeout: float = None,
     ) -> None:
         __tracebackhide__ = True
+        if attached is None:
+            attached = True
+        attached_string = "attached" if attached else "detached"
         await self._expect_impl(
-            (
-                "to.be.attached"
-                if (attached is None or attached is True)
-                else "to.be.detached"
-            ),
+            ("to.be.attached" if attached else "to.be.detached"),
             FrameExpectOptions(timeout=timeout),
             None,
-            "Locator expected to be attached",
+            f"Locator expected to be {attached_string}",
         )
 
     async def to_be_checked(
@@ -528,15 +527,14 @@ async def to_be_checked(
         checked: bool = None,
     ) -> None:
         __tracebackhide__ = True
+        if checked is None:
+            checked = True
+        checked_string = "checked" if checked else "unchecked"
         await self._expect_impl(
-            (
-                "to.be.checked"
-                if checked is None or checked is True
-                else "to.be.unchecked"
-            ),
+            ("to.be.checked" if checked else "to.be.unchecked"),
             FrameExpectOptions(timeout=timeout),
             None,
-            "Locator expected to be checked",
+            f"Locator expected to be {checked_string}",
         )
 
     async def not_to_be_attached(
@@ -581,11 +579,12 @@ async def to_be_editable(
         __tracebackhide__ = True
         if editable is None:
             editable = True
+        editable_string = "editable" if editable else "readonly"
         await self._expect_impl(
             "to.be.editable" if editable else "to.be.readonly",
             FrameExpectOptions(timeout=timeout),
             None,
-            "Locator expected to be editable",
+            f"Locator expected to be {editable_string}",
         )
 
     async def not_to_be_editable(
@@ -623,11 +622,12 @@ async def to_be_enabled(
         __tracebackhide__ = True
         if enabled is None:
             enabled = True
+        enabled_string = "enabled" if enabled else "disabled"
         await self._expect_impl(
             "to.be.enabled" if enabled else "to.be.disabled",
             FrameExpectOptions(timeout=timeout),
             None,
-            "Locator expected to be enabled",
+            f"Locator expected to be {enabled_string}",
         )
 
     async def not_to_be_enabled(
@@ -665,11 +665,12 @@ async def to_be_visible(
         __tracebackhide__ = True
         if visible is None:
             visible = True
+        visible_string = "visible" if visible else "hidden"
         await self._expect_impl(
             "to.be.visible" if visible else "to.be.hidden",
             FrameExpectOptions(timeout=timeout),
             None,
-            "Locator expected to be visible",
+            f"Locator expected to be {visible_string}",
         )
 
     async def not_to_be_visible(
diff --git a/tests/async/test_assertions.py b/tests/async/test_assertions.py
index d61e625c7..88b9c1b4f 100644
--- a/tests/async/test_assertions.py
+++ b/tests/async/test_assertions.py
@@ -510,14 +510,14 @@ async def test_assertions_locator_to_be_checked(page: Page, server: Server) -> N
     await page.set_content("<input type=checkbox>")
     my_checkbox = page.locator("input")
     await expect(my_checkbox).not_to_be_checked()
-    with pytest.raises(AssertionError):
+    with pytest.raises(AssertionError, match="Locator expected to be checked"):
         await expect(my_checkbox).to_be_checked(timeout=100)
     await expect(my_checkbox).to_be_checked(timeout=100, checked=False)
     with pytest.raises(AssertionError):
         await expect(my_checkbox).to_be_checked(timeout=100, checked=True)
     await my_checkbox.check()
     await expect(my_checkbox).to_be_checked(timeout=100, checked=True)
-    with pytest.raises(AssertionError):
+    with pytest.raises(AssertionError, match="Locator expected to be unchecked"):
         await expect(my_checkbox).to_be_checked(timeout=100, checked=False)
     await expect(my_checkbox).to_be_checked()
 
@@ -534,19 +534,91 @@ async def test_assertions_locator_to_be_disabled_enabled(
         await expect(my_checkbox).to_be_disabled(timeout=100)
     await my_checkbox.evaluate("e => e.disabled = true")
     await expect(my_checkbox).to_be_disabled()
-    with pytest.raises(AssertionError):
+    with pytest.raises(AssertionError, match="Locator expected to be enabled"):
         await expect(my_checkbox).to_be_enabled(timeout=100)
 
 
+async def test_assertions_locator_to_be_enabled_with_true(page: Page) -> None:
+    await page.set_content("<button>Text</button>")
+    await expect(page.locator("button")).to_be_enabled(enabled=True)
+
+
+async def test_assertions_locator_to_be_enabled_with_false_throws_good_exception(
+    page: Page,
+) -> None:
+    await page.set_content("<button>Text</button>")
+    with pytest.raises(AssertionError, match="Locator expected to be disabled"):
+        await expect(page.locator("button")).to_be_enabled(enabled=False)
+
+
+async def test_assertions_locator_to_be_enabled_with_false(page: Page) -> None:
+    await page.set_content("<button disabled>Text</button>")
+    await expect(page.locator("button")).to_be_enabled(enabled=False)
+
+
+async def test_assertions_locator_to_be_enabled_with_not_and_false(page: Page) -> None:
+    await page.set_content("<button>Text</button>")
+    await expect(page.locator("button")).not_to_be_enabled(enabled=False)
+
+
+async def test_assertions_locator_to_be_enabled_eventually(page: Page) -> None:
+    await page.set_content("<button disabled>Text</button>")
+    await page.eval_on_selector(
+        "button",
+        """
+        button => setTimeout(() => {
+            button.removeAttribute('disabled');
+        }, 700);
+    """,
+    )
+    await expect(page.locator("button")).to_be_enabled()
+
+
+async def test_assertions_locator_to_be_enabled_eventually_with_not(page: Page) -> None:
+    await page.set_content("<button>Text</button>")
+    await page.eval_on_selector(
+        "button",
+        """
+        button => setTimeout(() => {
+            button.setAttribute('disabled', '');
+        }, 700);
+    """,
+    )
+    await expect(page.locator("button")).not_to_be_enabled()
+
+
 async def test_assertions_locator_to_be_editable(page: Page, server: Server) -> None:
     await page.goto(server.EMPTY_PAGE)
     await page.set_content("<input></input><button disabled>Text</button>")
     await expect(page.locator("button")).not_to_be_editable()
     await expect(page.locator("input")).to_be_editable()
-    with pytest.raises(AssertionError):
+    with pytest.raises(AssertionError, match="Locator expected to be editable"):
         await expect(page.locator("button")).to_be_editable(timeout=100)
 
 
+async def test_assertions_locator_to_be_editable_with_true(page: Page) -> None:
+    await page.set_content("<input></input>")
+    await expect(page.locator("input")).to_be_editable(editable=True)
+
+
+async def test_assertions_locator_to_be_editable_with_false(page: Page) -> None:
+    await page.set_content("<input readonly></input>")
+    await expect(page.locator("input")).to_be_editable(editable=False)
+
+
+async def test_assertions_locator_to_be_editable_with_false_and_throw_good_exception(
+    page: Page,
+) -> None:
+    await page.set_content("<input></input>")
+    with pytest.raises(AssertionError, match="Locator expected to be readonly"):
+        await expect(page.locator("input")).to_be_editable(editable=False)
+
+
+async def test_assertions_locator_to_be_editable_with_not_and_false(page: Page) -> None:
+    await page.set_content("<input></input>")
+    await expect(page.locator("input")).not_to_be_editable(editable=False)
+
+
 async def test_assertions_locator_to_be_empty(page: Page, server: Server) -> None:
     await page.goto(server.EMPTY_PAGE)
     await page.set_content(
@@ -579,10 +651,59 @@ async def test_assertions_locator_to_be_hidden_visible(
         await expect(my_checkbox).to_be_hidden(timeout=100)
     await my_checkbox.evaluate("e => e.style.display = 'none'")
     await expect(my_checkbox).to_be_hidden()
-    with pytest.raises(AssertionError):
+    with pytest.raises(AssertionError, match="Locator expected to be visible"):
         await expect(my_checkbox).to_be_visible(timeout=100)
 
 
+async def test_assertions_locator_to_be_visible_with_true(page: Page) -> None:
+    await page.set_content("<button>hello</button>")
+    await expect(page.locator("button")).to_be_visible(visible=True)
+
+
+async def test_assertions_locator_to_be_visible_with_false(page: Page) -> None:
+    await page.set_content("<button hidden>hello</button>")
+    await expect(page.locator("button")).to_be_visible(visible=False)
+
+
+async def test_assertions_locator_to_be_visible_with_false_throws_good_exception(
+    page: Page,
+) -> None:
+    await page.set_content("<button>hello</button>")
+    with pytest.raises(AssertionError, match="Locator expected to be hidden"):
+        await expect(page.locator("button")).to_be_visible(visible=False)
+
+
+async def test_assertions_locator_to_be_visible_with_not_and_false(page: Page) -> None:
+    await page.set_content("<button>hello</button>")
+    await expect(page.locator("button")).not_to_be_visible(visible=False)
+
+
+async def test_assertions_locator_to_be_visible_eventually(page: Page) -> None:
+    await page.set_content("<div></div>")
+    await page.eval_on_selector(
+        "div",
+        """
+        div => setTimeout(() => {
+            div.innerHTML = '<span>Hello</span>';
+        }, 700);
+    """,
+    )
+    await expect(page.locator("span")).to_be_visible()
+
+
+async def test_assertions_locator_to_be_visible_eventually_with_not(page: Page) -> None:
+    await page.set_content("<div><span>Hello</span></div>")
+    await page.eval_on_selector(
+        "span",
+        """
+        span => setTimeout(() => {
+            span.textContent = '';
+        }, 700);
+    """,
+    )
+    await expect(page.locator("span")).not_to_be_visible()
+
+
 async def test_assertions_should_serialize_regexp_correctly(
     page: Page, server: Server
 ) -> None:
@@ -746,6 +867,15 @@ async def test_should_be_attached_with_attached_false(page: Page) -> None:
     await expect(locator).to_be_attached(attached=False)
 
 
+async def test_should_be_attached_with_attached_false_and_throw_good_error(
+    page: Page,
+) -> None:
+    await page.set_content("<button>hello</button>")
+    locator = page.locator("button")
+    with pytest.raises(AssertionError, match="Locator expected to be detached"):
+        await expect(locator).to_be_attached(attached=False, timeout=1)
+
+
 async def test_should_be_attached_with_not_and_attached_false(page: Page) -> None:
     await page.set_content("<button>hello</button>")
     locator = page.locator("button")
@@ -773,7 +903,9 @@ async def test_should_be_attached_eventually_with_not(page: Page) -> None:
 async def test_should_be_attached_fail(page: Page) -> None:
     await page.set_content("<button>Hello</button>")
     locator = page.locator("input")
-    with pytest.raises(AssertionError) as exc_info:
+    with pytest.raises(
+        AssertionError, match="Locator expected to be attached"
+    ) as exc_info:
         await expect(locator).to_be_attached(timeout=1000)
     assert "locator resolved to" not in exc_info.value.args[0]
 
diff --git a/tests/sync/test_assertions.py b/tests/sync/test_assertions.py
index d7180fc94..6f27e0a25 100644
--- a/tests/sync/test_assertions.py
+++ b/tests/sync/test_assertions.py
@@ -490,14 +490,14 @@ def test_assertions_locator_to_be_checked(page: Page, server: Server) -> None:
     page.set_content("<input type=checkbox>")
     my_checkbox = page.locator("input")
     expect(my_checkbox).not_to_be_checked()
-    with pytest.raises(AssertionError):
+    with pytest.raises(AssertionError, match="Locator expected to be checked"):
         expect(my_checkbox).to_be_checked(timeout=100)
     expect(my_checkbox).to_be_checked(timeout=100, checked=False)
     with pytest.raises(AssertionError):
         expect(my_checkbox).to_be_checked(timeout=100, checked=True)
     my_checkbox.check()
     expect(my_checkbox).to_be_checked(timeout=100, checked=True)
-    with pytest.raises(AssertionError):
+    with pytest.raises(AssertionError, match="Locator expected to be unchecked"):
         expect(my_checkbox).to_be_checked(timeout=100, checked=False)
     expect(my_checkbox).to_be_checked()
 
@@ -512,7 +512,7 @@ def test_assertions_locator_to_be_disabled_enabled(page: Page, server: Server) -
         expect(my_checkbox).to_be_disabled(timeout=100)
     my_checkbox.evaluate("e => e.disabled = true")
     expect(my_checkbox).to_be_disabled()
-    with pytest.raises(AssertionError):
+    with pytest.raises(AssertionError, match="Locator expected to be enabled"):
         expect(my_checkbox).to_be_enabled(timeout=100)
 
 
@@ -521,6 +521,14 @@ def test_assertions_locator_to_be_enabled_with_true(page: Page) -> None:
     expect(page.locator("button")).to_be_enabled(enabled=True)
 
 
+def test_assertions_locator_to_be_enabled_with_false_throws_good_exception(
+    page: Page,
+) -> None:
+    page.set_content("<button>Text</button>")
+    with pytest.raises(AssertionError, match="Locator expected to be disabled"):
+        expect(page.locator("button")).to_be_enabled(enabled=False)
+
+
 def test_assertions_locator_to_be_enabled_with_false(page: Page) -> None:
     page.set_content("<button disabled>Text</button>")
     expect(page.locator("button")).to_be_enabled(enabled=False)
@@ -562,7 +570,7 @@ def test_assertions_locator_to_be_editable(page: Page, server: Server) -> None:
     page.set_content("<input></input><button disabled>Text</button>")
     expect(page.locator("button")).not_to_be_editable()
     expect(page.locator("input")).to_be_editable()
-    with pytest.raises(AssertionError):
+    with pytest.raises(AssertionError, match="Locator expected to be editable"):
         expect(page.locator("button")).to_be_editable(timeout=100)
 
 
@@ -576,6 +584,14 @@ def test_assertions_locator_to_be_editable_with_false(page: Page) -> None:
     expect(page.locator("input")).to_be_editable(editable=False)
 
 
+def test_assertions_locator_to_be_editable_with_false_and_throw_good_exception(
+    page: Page,
+) -> None:
+    page.set_content("<input></input>")
+    with pytest.raises(AssertionError, match="Locator expected to be readonly"):
+        expect(page.locator("input")).to_be_editable(editable=False)
+
+
 def test_assertions_locator_to_be_editable_with_not_and_false(page: Page) -> None:
     page.set_content("<input></input>")
     expect(page.locator("input")).not_to_be_editable(editable=False)
@@ -611,7 +627,7 @@ def test_assertions_locator_to_be_hidden_visible(page: Page, server: Server) ->
         expect(my_checkbox).to_be_hidden(timeout=100)
     my_checkbox.evaluate("e => e.style.display = 'none'")
     expect(my_checkbox).to_be_hidden()
-    with pytest.raises(AssertionError):
+    with pytest.raises(AssertionError, match="Locator expected to be visible"):
         expect(my_checkbox).to_be_visible(timeout=100)
 
 
@@ -625,6 +641,14 @@ def test_assertions_locator_to_be_visible_with_false(page: Page) -> None:
     expect(page.locator("button")).to_be_visible(visible=False)
 
 
+def test_assertions_locator_to_be_visible_with_false_throws_good_exception(
+    page: Page,
+) -> None:
+    page.set_content("<button>hello</button>")
+    with pytest.raises(AssertionError, match="Locator expected to be hidden"):
+        expect(page.locator("button")).to_be_visible(visible=False)
+
+
 def test_assertions_locator_to_be_visible_with_not_and_false(page: Page) -> None:
     page.set_content("<button>hello</button>")
     expect(page.locator("button")).not_to_be_visible(visible=False)
@@ -813,6 +837,15 @@ def test_should_be_attached_with_attached_false(page: Page) -> None:
     expect(locator).to_be_attached(attached=False)
 
 
+def test_should_be_attached_with_attached_false_and_throw_good_error(
+    page: Page,
+) -> None:
+    page.set_content("<button>hello</button>")
+    locator = page.locator("button")
+    with pytest.raises(AssertionError, match="Locator expected to be detached"):
+        expect(locator).to_be_attached(attached=False, timeout=1)
+
+
 def test_should_be_attached_with_not_and_attached_false(page: Page) -> None:
     page.set_content("<button>hello</button>")
     locator = page.locator("button")
@@ -838,7 +871,9 @@ def test_should_be_attached_eventually_with_not(page: Page) -> None:
 def test_should_be_attached_fail(page: Page) -> None:
     page.set_content("<button>Hello</button>")
     locator = page.locator("input")
-    with pytest.raises(AssertionError) as exc_info:
+    with pytest.raises(
+        AssertionError, match="Locator expected to be attached"
+    ) as exc_info:
         expect(locator).to_be_attached(timeout=1000)
     assert "locator resolved to" not in exc_info.value.args[0]