diff --git a/Cargo.lock b/Cargo.lock
index 2e3b216e73..e327350524 100644
--- a/Cargo.lock
+++ b/Cargo.lock
@@ -903,7 +903,7 @@ dependencies = [
  "iana-time-zone-haiku",
  "js-sys",
  "wasm-bindgen",
- "windows-core",
+ "windows-core 0.52.0",
 ]
 
 [[package]]
@@ -3185,11 +3185,11 @@ checksum = "712e227841d057c1ee1cd2fb22fa7e5a5461ae8e48fa2ca79ec42cfc1931183f"
 
 [[package]]
 name = "windows"
-version = "0.52.0"
+version = "0.57.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "e48a53791691ab099e5e2ad123536d0fff50652600abaf43bbf952894110d0be"
+checksum = "12342cb4d8e3b046f3d80effd474a7a02447231330ef77d71daa6fbc40681143"
 dependencies = [
- "windows-core",
+ "windows-core 0.57.0",
  "windows-targets 0.52.6",
 ]
 
@@ -3202,6 +3202,49 @@ dependencies = [
  "windows-targets 0.52.6",
 ]
 
+[[package]]
+name = "windows-core"
+version = "0.57.0"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "d2ed2439a290666cd67ecce2b0ffaad89c2a56b976b736e6ece670297897832d"
+dependencies = [
+ "windows-implement",
+ "windows-interface",
+ "windows-result",
+ "windows-targets 0.52.6",
+]
+
+[[package]]
+name = "windows-implement"
+version = "0.57.0"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "9107ddc059d5b6fbfbffdfa7a7fe3e22a226def0b2608f72e9d552763d3e1ad7"
+dependencies = [
+ "proc-macro2",
+ "quote",
+ "syn 2.0.98",
+]
+
+[[package]]
+name = "windows-interface"
+version = "0.57.0"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "29bee4b38ea3cde66011baa44dba677c432a78593e202392d1e9070cf2a7fca7"
+dependencies = [
+ "proc-macro2",
+ "quote",
+ "syn 2.0.98",
+]
+
+[[package]]
+name = "windows-result"
+version = "0.1.2"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "5e383302e8ec8515204254685643de10811af0ed97ea37210dc26fb0032647f8"
+dependencies = [
+ "windows-targets 0.52.6",
+]
+
 [[package]]
 name = "windows-sys"
 version = "0.36.1"
@@ -3395,12 +3438,12 @@ checksum = "589f6da84c646204747d1270a2a5661ea66ed1cced2631d546fdfb155959f9ec"
 
 [[package]]
 name = "winreg"
-version = "0.52.0"
+version = "0.55.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "a277a57398d4bfa075df44f501a17cfdf8542d224f0d36095a2adc7aee4ef0a5"
+checksum = "cb5a765337c50e9ec252c2069be9bf91c7df47afb103b642ba3a53bf8101be97"
 dependencies = [
  "cfg-if",
- "windows-sys 0.48.0",
+ "windows-sys 0.59.0",
 ]
 
 [[package]]
diff --git a/vm/Cargo.toml b/vm/Cargo.toml
index 1468651aeb..f092e153a0 100644
--- a/vm/Cargo.toml
+++ b/vm/Cargo.toml
@@ -108,7 +108,7 @@ num_cpus = "1.13.1"
 [target.'cfg(windows)'.dependencies]
 junction = { workspace = true }
 schannel = { workspace = true }
-winreg = "0.52"
+winreg = "0.55"
 
 [target.'cfg(windows)'.dependencies.windows]
 version = "0.52.0"
diff --git a/vm/src/stdlib/winreg.rs b/vm/src/stdlib/winreg.rs
index b368c43a3e..747c58cfd8 100644
--- a/vm/src/stdlib/winreg.rs
+++ b/vm/src/stdlib/winreg.rs
@@ -98,7 +98,7 @@ mod winreg {
 
         #[pymethod(magic)]
         fn bool(&self) -> bool {
-            self.key().raw_handle() != 0
+            !self.key().raw_handle().is_null()
         }
         #[pymethod(magic)]
         fn enter(zelf: PyRef<Self>) -> PyRef<Self> {