diff --git a/crates/ruff/resources/test/fixtures/flake8_pytest_style/PT009.py b/crates/ruff/resources/test/fixtures/flake8_pytest_style/PT009.py
index e99d8e06a84ff..e25aef6facff9 100644
--- a/crates/ruff/resources/test/fixtures/flake8_pytest_style/PT009.py
+++ b/crates/ruff/resources/test/fixtures/flake8_pytest_style/PT009.py
@@ -17,6 +17,12 @@ def test_assert_true(self):
         self.assertTrue(**{"expr": expr, "msg": msg})  # Error, unfixable
         self.assertTrue(msg=msg, expr=expr, unexpected_arg=False)  # Error, unfixable
         self.assertTrue(msg=msg)  # Error, unfixable
+        (
+            self.assertIsNotNone(value)  # Error, unfixable
+            if expect_condition
+            else self.assertIsNone(value)  # Error, unfixable
+        )
+        return self.assertEqual(True,  False)  # Error, unfixable
 
     def test_assert_false(self):
         self.assertFalse(True)  # Error
diff --git a/crates/ruff/src/rules/flake8_pytest_style/rules/assertion.rs b/crates/ruff/src/rules/flake8_pytest_style/rules/assertion.rs
index 0b5ebfbb22444..6e96447f934b7 100644
--- a/crates/ruff/src/rules/flake8_pytest_style/rules/assertion.rs
+++ b/crates/ruff/src/rules/flake8_pytest_style/rules/assertion.rs
@@ -12,7 +12,7 @@ use crate::checkers::ast::Checker;
 use crate::fix::Fix;
 use crate::registry::Diagnostic;
 use crate::source_code::Stylist;
-use crate::violation::{AlwaysAutofixableViolation, AutofixKind, Availability, Violation};
+use crate::violation::{AutofixKind, Availability, Violation};
 
 use super::helpers::is_falsy_constant;
 use super::unittest_assert::UnittestAssert;
@@ -94,18 +94,23 @@ impl Violation for AssertAlwaysFalse {
 define_violation!(
     pub struct UnittestAssertion {
         pub assertion: String,
+        pub fixable: bool,
     }
 );
-impl AlwaysAutofixableViolation for UnittestAssertion {
+impl Violation for UnittestAssertion {
+    const AUTOFIX: Option<AutofixKind> = Some(AutofixKind::new(Availability::Sometimes));
+
     #[derive_message_formats]
     fn message(&self) -> String {
-        let UnittestAssertion { assertion } = self;
+        let UnittestAssertion { assertion, .. } = self;
         format!("Use a regular `assert` instead of unittest-style `{assertion}`")
     }
 
-    fn autofix_title(&self) -> String {
-        let UnittestAssertion { assertion } = self;
-        format!("Replace `{assertion}(...)` with `assert ...`")
+    fn autofix_title_formatter(&self) -> Option<fn(&Self) -> String> {
+        self.fixable
+            .then_some(|UnittestAssertion { assertion, .. }| {
+                format!("Replace `{assertion}(...)` with `assert ...`")
+            })
     }
 }
 
@@ -181,13 +186,18 @@ pub fn unittest_assertion(
     match &func.node {
         ExprKind::Attribute { attr, .. } => {
             if let Ok(unittest_assert) = UnittestAssert::try_from(attr.as_str()) {
+                // We're converting an expression to a statement, so avoid applying the fix if
+                // the assertion is part of a larger expression.
+                let fixable = checker.current_expr_parent().is_none()
+                    && matches!(checker.current_stmt().node, StmtKind::Expr { .. });
                 let mut diagnostic = Diagnostic::new(
                     UnittestAssertion {
                         assertion: unittest_assert.to_string(),
+                        fixable,
                     },
                     Range::from_located(func),
                 );
-                if checker.patch(diagnostic.kind.rule()) {
+                if fixable && checker.patch(diagnostic.kind.rule()) {
                     if let Ok(stmt) = unittest_assert.generate_assert(args, keywords) {
                         diagnostic.amend(Fix::replacement(
                             unparse_stmt(&stmt, checker.stylist),
diff --git a/crates/ruff/src/rules/flake8_pytest_style/snapshots/ruff__rules__flake8_pytest_style__tests__PT009.snap b/crates/ruff/src/rules/flake8_pytest_style/snapshots/ruff__rules__flake8_pytest_style__tests__PT009.snap
index 091437ec0144e..70357b21a4893 100644
--- a/crates/ruff/src/rules/flake8_pytest_style/snapshots/ruff__rules__flake8_pytest_style__tests__PT009.snap
+++ b/crates/ruff/src/rules/flake8_pytest_style/snapshots/ruff__rules__flake8_pytest_style__tests__PT009.snap
@@ -5,6 +5,7 @@ expression: diagnostics
 - kind:
     UnittestAssertion:
       assertion: assertTrue
+      fixable: true
   location:
     row: 11
     column: 8
@@ -24,6 +25,7 @@ expression: diagnostics
 - kind:
     UnittestAssertion:
       assertion: assertTrue
+      fixable: true
   location:
     row: 12
     column: 8
@@ -43,6 +45,7 @@ expression: diagnostics
 - kind:
     UnittestAssertion:
       assertion: assertTrue
+      fixable: true
   location:
     row: 13
     column: 8
@@ -62,6 +65,7 @@ expression: diagnostics
 - kind:
     UnittestAssertion:
       assertion: assertTrue
+      fixable: true
   location:
     row: 14
     column: 8
@@ -81,6 +85,7 @@ expression: diagnostics
 - kind:
     UnittestAssertion:
       assertion: assertTrue
+      fixable: true
   location:
     row: 15
     column: 8
@@ -100,6 +105,7 @@ expression: diagnostics
 - kind:
     UnittestAssertion:
       assertion: assertTrue
+      fixable: true
   location:
     row: 16
     column: 8
@@ -111,6 +117,7 @@ expression: diagnostics
 - kind:
     UnittestAssertion:
       assertion: assertTrue
+      fixable: true
   location:
     row: 17
     column: 8
@@ -122,6 +129,7 @@ expression: diagnostics
 - kind:
     UnittestAssertion:
       assertion: assertTrue
+      fixable: true
   location:
     row: 18
     column: 8
@@ -133,6 +141,7 @@ expression: diagnostics
 - kind:
     UnittestAssertion:
       assertion: assertTrue
+      fixable: true
   location:
     row: 19
     column: 8
@@ -141,365 +150,420 @@ expression: diagnostics
     column: 23
   fix: ~
   parent: ~
+- kind:
+    UnittestAssertion:
+      assertion: assertIsNotNone
+      fixable: false
+  location:
+    row: 21
+    column: 12
+  end_location:
+    row: 21
+    column: 32
+  fix: ~
+  parent: ~
+- kind:
+    UnittestAssertion:
+      assertion: assertIsNone
+      fixable: false
+  location:
+    row: 23
+    column: 17
+  end_location:
+    row: 23
+    column: 34
+  fix: ~
+  parent: ~
+- kind:
+    UnittestAssertion:
+      assertion: assertEqual
+      fixable: false
+  location:
+    row: 25
+    column: 15
+  end_location:
+    row: 25
+    column: 31
+  fix: ~
+  parent: ~
 - kind:
     UnittestAssertion:
       assertion: assertFalse
+      fixable: true
   location:
-    row: 22
+    row: 28
     column: 8
   end_location:
-    row: 22
+    row: 28
     column: 24
   fix:
     content:
       - assert not True
     location:
-      row: 22
+      row: 28
       column: 8
     end_location:
-      row: 22
+      row: 28
       column: 30
   parent: ~
 - kind:
     UnittestAssertion:
       assertion: assertEqual
+      fixable: true
   location:
-    row: 25
+    row: 31
     column: 8
   end_location:
-    row: 25
+    row: 31
     column: 24
   fix:
     content:
       - assert 1 == 2
     location:
-      row: 25
+      row: 31
       column: 8
     end_location:
-      row: 25
+      row: 31
       column: 30
   parent: ~
 - kind:
     UnittestAssertion:
       assertion: assertNotEqual
+      fixable: true
   location:
-    row: 28
+    row: 34
     column: 8
   end_location:
-    row: 28
+    row: 34
     column: 27
   fix:
     content:
       - assert 1 != 1
     location:
-      row: 28
+      row: 34
       column: 8
     end_location:
-      row: 28
+      row: 34
       column: 33
   parent: ~
 - kind:
     UnittestAssertion:
       assertion: assertGreater
+      fixable: true
   location:
-    row: 31
+    row: 37
     column: 8
   end_location:
-    row: 31
+    row: 37
     column: 26
   fix:
     content:
       - assert 1 > 2
     location:
-      row: 31
+      row: 37
       column: 8
     end_location:
-      row: 31
+      row: 37
       column: 32
   parent: ~
 - kind:
     UnittestAssertion:
       assertion: assertGreaterEqual
+      fixable: true
   location:
-    row: 34
+    row: 40
     column: 8
   end_location:
-    row: 34
+    row: 40
     column: 31
   fix:
     content:
       - assert 1 >= 2
     location:
-      row: 34
+      row: 40
       column: 8
     end_location:
-      row: 34
+      row: 40
       column: 37
   parent: ~
 - kind:
     UnittestAssertion:
       assertion: assertLess
+      fixable: true
   location:
-    row: 37
+    row: 43
     column: 8
   end_location:
-    row: 37
+    row: 43
     column: 23
   fix:
     content:
       - assert 2 < 1
     location:
-      row: 37
+      row: 43
       column: 8
     end_location:
-      row: 37
+      row: 43
       column: 29
   parent: ~
 - kind:
     UnittestAssertion:
       assertion: assertLessEqual
+      fixable: true
   location:
-    row: 40
+    row: 46
     column: 8
   end_location:
-    row: 40
+    row: 46
     column: 28
   fix:
     content:
       - assert 1 <= 2
     location:
-      row: 40
+      row: 46
       column: 8
     end_location:
-      row: 40
+      row: 46
       column: 34
   parent: ~
 - kind:
     UnittestAssertion:
       assertion: assertIn
+      fixable: true
   location:
-    row: 43
+    row: 49
     column: 8
   end_location:
-    row: 43
+    row: 49
     column: 21
   fix:
     content:
       - "assert 1 in [2, 3]"
     location:
-      row: 43
+      row: 49
       column: 8
     end_location:
-      row: 43
+      row: 49
       column: 32
   parent: ~
 - kind:
     UnittestAssertion:
       assertion: assertNotIn
+      fixable: true
   location:
-    row: 46
+    row: 52
     column: 8
   end_location:
-    row: 46
+    row: 52
     column: 24
   fix:
     content:
       - "assert 2 not in [2, 3]"
     location:
-      row: 46
+      row: 52
       column: 8
     end_location:
-      row: 46
+      row: 52
       column: 35
   parent: ~
 - kind:
     UnittestAssertion:
       assertion: assertIsNone
+      fixable: true
   location:
-    row: 49
+    row: 55
     column: 8
   end_location:
-    row: 49
+    row: 55
     column: 25
   fix:
     content:
       - assert 0 is None
     location:
-      row: 49
+      row: 55
       column: 8
     end_location:
-      row: 49
+      row: 55
       column: 28
   parent: ~
 - kind:
     UnittestAssertion:
       assertion: assertIsNotNone
+      fixable: true
   location:
-    row: 52
+    row: 58
     column: 8
   end_location:
-    row: 52
+    row: 58
     column: 28
   fix:
     content:
       - assert 0 is not None
     location:
-      row: 52
+      row: 58
       column: 8
     end_location:
-      row: 52
+      row: 58
       column: 31
   parent: ~
 - kind:
     UnittestAssertion:
       assertion: assertIs
+      fixable: true
   location:
-    row: 55
+    row: 61
     column: 8
   end_location:
-    row: 55
+    row: 61
     column: 21
   fix:
     content:
       - "assert [] is []"
     location:
-      row: 55
+      row: 61
       column: 8
     end_location:
-      row: 55
+      row: 61
       column: 29
   parent: ~
 - kind:
     UnittestAssertion:
       assertion: assertIsNot
+      fixable: true
   location:
-    row: 58
+    row: 64
     column: 8
   end_location:
-    row: 58
+    row: 64
     column: 24
   fix:
     content:
       - assert 1 is not 1
     location:
-      row: 58
+      row: 64
       column: 8
     end_location:
-      row: 58
+      row: 64
       column: 30
   parent: ~
 - kind:
     UnittestAssertion:
       assertion: assertIsInstance
+      fixable: true
   location:
-    row: 61
+    row: 67
     column: 8
   end_location:
-    row: 61
+    row: 67
     column: 29
   fix:
     content:
       - "assert isinstance(1, str)"
     location:
-      row: 61
+      row: 67
       column: 8
     end_location:
-      row: 61
+      row: 67
       column: 37
   parent: ~
 - kind:
     UnittestAssertion:
       assertion: assertNotIsInstance
+      fixable: true
   location:
-    row: 64
+    row: 70
     column: 8
   end_location:
-    row: 64
+    row: 70
     column: 32
   fix:
     content:
       - "assert not isinstance(1, int)"
     location:
-      row: 64
+      row: 70
       column: 8
     end_location:
-      row: 64
+      row: 70
       column: 40
   parent: ~
 - kind:
     UnittestAssertion:
       assertion: assertRegex
+      fixable: true
   location:
-    row: 67
+    row: 73
     column: 8
   end_location:
-    row: 67
+    row: 73
     column: 24
   fix:
     content:
       - "assert re.search(\"def\", \"abc\")"
     location:
-      row: 67
+      row: 73
       column: 8
     end_location:
-      row: 67
+      row: 73
       column: 39
   parent: ~
 - kind:
     UnittestAssertion:
       assertion: assertNotRegex
+      fixable: true
   location:
-    row: 70
+    row: 76
     column: 8
   end_location:
-    row: 70
+    row: 76
     column: 27
   fix:
     content:
       - "assert not re.search(\"abc\", \"abc\")"
     location:
-      row: 70
+      row: 76
       column: 8
     end_location:
-      row: 70
+      row: 76
       column: 42
   parent: ~
 - kind:
     UnittestAssertion:
       assertion: assertRegexpMatches
+      fixable: true
   location:
-    row: 73
+    row: 79
     column: 8
   end_location:
-    row: 73
+    row: 79
     column: 32
   fix:
     content:
       - "assert re.search(\"def\", \"abc\")"
     location:
-      row: 73
+      row: 79
       column: 8
     end_location:
-      row: 73
+      row: 79
       column: 47
   parent: ~
 - kind:
     UnittestAssertion:
       assertion: assertNotRegex
+      fixable: true
   location:
-    row: 76
+    row: 82
     column: 8
   end_location:
-    row: 76
+    row: 82
     column: 27
   fix:
     content:
       - "assert not re.search(\"abc\", \"abc\")"
     location:
-      row: 76
+      row: 82
       column: 8
     end_location:
-      row: 76
+      row: 82
       column: 42
   parent: ~