diff --git a/newsfragments/5571.fixed.md b/newsfragments/5571.fixed.md
new file mode 100644
index 00000000000..62d27103903
--- /dev/null
+++ b/newsfragments/5571.fixed.md
@@ -0,0 +1,2 @@
+Fix linking with libpython under Cygwin
+Bumped `target-lexicon` dependency to 0.13.3 for Cygwin support.
\ No newline at end of file
diff --git a/pyo3-build-config/Cargo.toml b/pyo3-build-config/Cargo.toml
index cd7cd52b73f..2f711915b8d 100644
--- a/pyo3-build-config/Cargo.toml
+++ b/pyo3-build-config/Cargo.toml
@@ -13,11 +13,11 @@ rust-version.workspace = true
 
 [dependencies]
 python3-dll-a = { version = "0.2.12", optional = true }
-target-lexicon = "0.13"
+target-lexicon = "0.13.3"
 
 [build-dependencies]
 python3-dll-a = { version = "0.2.12", optional = true }
-target-lexicon = "0.13"
+target-lexicon = "0.13.3"
 
 [features]
 default = []
diff --git a/pyo3-build-config/src/impl_.rs b/pyo3-build-config/src/impl_.rs
index cca9393d873..b977ac79479 100644
--- a/pyo3-build-config/src/impl_.rs
+++ b/pyo3-build-config/src/impl_.rs
@@ -890,6 +890,7 @@ pub fn is_linking_libpython_for_target(target: &Triple) -> bool {
         || target.operating_system == OperatingSystem::Aix
         || target.environment == Environment::Android
         || target.environment == Environment::Androideabi
+        || target.operating_system == OperatingSystem::Cygwin
         || !is_extension_module()
 }