diff --git a/crates/pyrefly_python/src/sys_info.rs b/crates/pyrefly_python/src/sys_info.rs
index 8499559b2b..0d9a30dcda 100644
--- a/crates/pyrefly_python/src/sys_info.rs
+++ b/crates/pyrefly_python/src/sys_info.rs
@@ -516,6 +516,52 @@ impl SysInfo {
         Some(self.evaluate(x)?.to_bool())
     }
 
+    /// Return true/false only when evaluation depends on the configured Python environment.
+    pub fn evaluate_bool_with_sys_info(&self, x: &Expr) -> Option<bool> {
+        Self::depends_on_sys_info(x).then(|| self.evaluate_bool(x))?
+    }
+
+    fn depends_on_sys_info(x: &Expr) -> bool {
+        match x {
+            Expr::Compare(x) => {
+                Self::depends_on_sys_info(&x.left)
+                    || x.comparators.iter().any(Self::depends_on_sys_info)
+            }
+            Expr::Attribute(ExprAttribute { value, attr, .. }) => {
+                matches!(
+                    &**value,
+                    Expr::Name(name)
+                        if (&name.id == "sys" && matches!(attr.as_str(), "platform" | "version_info"))
+                            || (&name.id == "os" && attr.as_str() == "name")
+                            || Self::is_type_checking_constant_name(attr.as_str())
+                ) || Self::depends_on_sys_info(value)
+            }
+            Expr::Name(name) => Self::is_type_checking_constant_name(name.id()),
+            Expr::Call(x) => {
+                Self::depends_on_sys_info(&x.func)
+                    || x.arguments.args.iter().any(Self::depends_on_sys_info)
+                    || x.arguments
+                        .keywords
+                        .iter()
+                        .any(|x| Self::depends_on_sys_info(&x.value))
+            }
+            Expr::Subscript(x) => {
+                Self::depends_on_sys_info(&x.value) || Self::depends_on_sys_info(&x.slice)
+            }
+            Expr::Tuple(x) => x.elts.iter().any(Self::depends_on_sys_info),
+            Expr::List(x) => x.elts.iter().any(Self::depends_on_sys_info),
+            Expr::Set(x) => x.elts.iter().any(Self::depends_on_sys_info),
+            Expr::BoolOp(x) => x.values.iter().any(Self::depends_on_sys_info),
+            Expr::UnaryOp(x) => Self::depends_on_sys_info(&x.operand),
+            Expr::Slice(x) => {
+                x.lower.as_deref().is_some_and(Self::depends_on_sys_info)
+                    || x.upper.as_deref().is_some_and(Self::depends_on_sys_info)
+                    || x.step.as_deref().is_some_and(Self::depends_on_sys_info)
+            }
+            _ => false,
+        }
+    }
+
     fn is_type_checking_constant_name(x: &str) -> bool {
         x == "TYPE_CHECKING" || x == "TYPE_CHECKING_WITH_PYREFLY"
     }
diff --git a/pyrefly/lib/alt/expr.rs b/pyrefly/lib/alt/expr.rs
index d52bd27898..ba6bc4835a 100644
--- a/pyrefly/lib/alt/expr.rs
+++ b/pyrefly/lib/alt/expr.rs
@@ -496,14 +496,24 @@ impl<'a, Ans: LookupAnswer> AnswersSolver<'a, Ans> {
             }
             Expr::If(x) => {
                 let condition_type = self.expr_infer(&x.test, errors);
-                let body_type = self.expr_infer_impl(&x.body, hint, errors).into_ty();
-                let orelse_type = self.expr_infer_impl(&x.orelse, hint, errors).into_ty();
                 self.check_dunder_bool_is_callable(&condition_type, x.range(), errors);
                 self.check_redundant_condition(&condition_type, x.range(), errors);
-                match self.as_bool(&condition_type, x.test.range(), errors) {
-                    Some(true) => body_type,
-                    Some(false) => orelse_type,
-                    None => self.union(body_type, orelse_type),
+                match self
+                    .bindings()
+                    .sys_info()
+                    .evaluate_bool_with_sys_info(&x.test)
+                {
+                    Some(true) => self.expr_infer_impl(&x.body, hint, errors).into_ty(),
+                    Some(false) => self.expr_infer_impl(&x.orelse, hint, errors).into_ty(),
+                    None => {
+                        let body_type = self.expr_infer_impl(&x.body, hint, errors).into_ty();
+                        let orelse_type = self.expr_infer_impl(&x.orelse, hint, errors).into_ty();
+                        match self.as_bool(&condition_type, x.test.range(), errors) {
+                            Some(true) => body_type,
+                            Some(false) => orelse_type,
+                            None => self.union(body_type, orelse_type),
+                        }
+                    }
                 }
             }
             Expr::BoolOp(x) => self.boolop(&x.values, x.op, hint, errors),
diff --git a/pyrefly/lib/binding/bindings.rs b/pyrefly/lib/binding/bindings.rs
index 54b557dbd0..5dd902dffb 100644
--- a/pyrefly/lib/binding/bindings.rs
+++ b/pyrefly/lib/binding/bindings.rs
@@ -196,6 +196,7 @@ table! {
 #[derive(Clone, Debug)]
 struct BindingsInner {
     module_info: ModuleInfo,
+    sys_info: SysInfo,
     table: BindingTable,
     metadata: Arc<BindingsMetadata>,
     /// Multi-line ranges and ignore-all directives, computed from the AST
@@ -351,6 +352,7 @@ impl Bindings {
         let module_info = Module::new(module_name, module_path, contents);
         Self(Arc::new(BindingsInner {
             module_info,
+            sys_info: SysInfo::default(),
             table: Default::default(),
             metadata: Arc::new(BindingsMetadata::new()),
             module_ranges: Arc::new(ModuleRanges {
@@ -382,6 +384,10 @@ impl Bindings {
         &self.0.module_info
     }
 
+    pub fn sys_info(&self) -> &SysInfo {
+        &self.0.sys_info
+    }
+
     pub fn metadata(&self) -> &Arc<BindingsMetadata> {
         &self.0.metadata
     }
@@ -736,6 +742,7 @@ impl Bindings {
         let module_deletes = scope_trace.module_deletes().clone();
         Self(Arc::new(BindingsInner {
             module_info,
+            sys_info: builder.sys_info,
             table: builder.table,
             metadata: Arc::new(builder.metadata),
             module_ranges,
diff --git a/pyrefly/lib/binding/expr.rs b/pyrefly/lib/binding/expr.rs
index 76c59cd7c3..d4387bd7dc 100644
--- a/pyrefly/lib/binding/expr.rs
+++ b/pyrefly/lib/binding/expr.rs
@@ -787,20 +787,49 @@ impl<'a> BindingsBuilder<'a> {
                 // Process the test before forking so walrus-defined names are
                 // in the base flow and visible to both branches.
                 self.ensure_expr(&mut x.test, &mut Usage::non_pinning_value_from(usage));
+                let static_test = self.sys_info.evaluate_bool_with_sys_info(&x.test);
                 let narrow_ops = NarrowOps::from_expr(self, Some(&x.test));
                 self.start_fork_and_branch(x.range);
-                self.bind_narrow_ops(&narrow_ops, NarrowUseLocation::Span(x.body.range()), usage);
-                self.ensure_expr(&mut x.body, usage);
-                // Negate the narrow ops for the `orelse`, then merge the Flows.
-                // TODO(stroxler): We eventually want to drop all narrows but merge values.
-                self.next_branch();
-                self.bind_narrow_ops(
-                    &narrow_ops.negate(),
-                    NarrowUseLocation::Span(x.range),
-                    usage,
-                );
-                self.ensure_expr(&mut x.orelse, usage);
-                self.finish_branch();
+                match static_test {
+                    Some(true) => {
+                        self.bind_narrow_ops(
+                            &narrow_ops,
+                            NarrowUseLocation::Span(x.body.range()),
+                            usage,
+                        );
+                        self.ensure_expr(&mut x.body, usage);
+                        self.finish_branch();
+                    }
+                    Some(false) => {
+                        self.abandon_branch();
+                        self.start_branch();
+                        self.bind_narrow_ops(
+                            &narrow_ops.negate(),
+                            NarrowUseLocation::Span(x.range),
+                            usage,
+                        );
+                        self.ensure_expr(&mut x.orelse, usage);
+                        self.finish_branch();
+                    }
+                    None => {
+                        self.bind_narrow_ops(
+                            &narrow_ops,
+                            NarrowUseLocation::Span(x.body.range()),
+                            usage,
+                        );
+                        self.ensure_expr(&mut x.body, usage);
+                        // Negate the narrow ops for the `orelse`, then merge the Flows.
+                        // TODO(stroxler): We eventually want to drop all narrows but merge values.
+                        self.next_branch();
+                        self.bind_narrow_ops(
+                            &narrow_ops.negate(),
+                            NarrowUseLocation::Span(x.range),
+                            usage,
+                        );
+                        self.ensure_expr(&mut x.orelse, usage);
+                        self.finish_branch();
+                    }
+                }
                 self.finish_exhaustive_fork();
             }
             Expr::BoolOp(ExprBoolOp {
diff --git a/pyrefly/lib/test/sys_info.rs b/pyrefly/lib/test/sys_info.rs
index 0e011fb158..2f2beb7e05 100644
--- a/pyrefly/lib/test/sys_info.rs
+++ b/pyrefly/lib/test/sys_info.rs
@@ -192,6 +192,35 @@ assert_type(Y(), int)
 "#,
 );
 
+testcase!(
+    test_platform_ternary_linux,
+    TestEnv::new_with_platform(PythonPlatform::linux()),
+    r#"
+import subprocess
+import sys
+
+value: int = subprocess.CREATE_NO_WINDOW if sys.platform == "win32" else 0
+inverted: int = 0 if sys.platform != "win32" else subprocess.CREATE_NO_WINDOW
+
+def condition() -> bool:
+    return False
+
+subprocess.CREATE_NO_WINDOW if condition() else 0  # E: No attribute `CREATE_NO_WINDOW` in module `subprocess`
+"#,
+);
+
+testcase!(
+    test_platform_ternary_windows,
+    TestEnv::new_with_platform(PythonPlatform::windows()),
+    r#"
+import subprocess
+import sys
+
+value: int = subprocess.CREATE_NO_WINDOW if sys.platform == "win32" else "not windows"
+inverted: int = "not windows" if sys.platform != "win32" else subprocess.CREATE_NO_WINDOW
+"#,
+);
+
 testcase!(
     test_platform_membership,
     r#"