diff --git a/macros/src/deps.rs b/macros/src/deps.rs
index 67305394..e38c96c5 100644
--- a/macros/src/deps.rs
+++ b/macros/src/deps.rs
@@ -1,54 +1,104 @@
+use std::{collections::HashSet, rc::Rc};
+
 use proc_macro2::TokenStream;
 use quote::{quote, ToTokens};
 use syn::{Path, Type};
 
 pub struct Dependencies {
-    dependencies: Vec<TokenStream>,
-    crate_rename: Path,
-    pub types: Vec<Type>,
+    crate_rename: Rc<Path>,
+    dependencies: HashSet<Dependency>,
+    types: HashSet<Rc<Type>>,
+}
+
+#[derive(Hash, Eq, PartialEq)]
+enum Dependency {
+    // A dependency on all dependencies of `ty`.
+    // This does not include a dependency on `ty` itself - only its dependencies!
+    Transitive {
+        crate_rename: Rc<Path>,
+        ty: Rc<Type>,
+    },
+    // A dependency on all type parameters of `ty`, as returned by `TS::generics()`.
+    // This does not include a dependency on `ty` itself.
+    Generics {
+        crate_rename: Rc<Path>,
+        ty: Rc<Type>,
+    },
+    Type(Rc<Type>),
 }
 
 impl Dependencies {
     pub fn new(crate_rename: Path) -> Self {
         Self {
-            dependencies: Vec::default(),
-            crate_rename,
-            types: Vec::default(),
+            dependencies: HashSet::new(),
+            crate_rename: Rc::new(crate_rename),
+            types: HashSet::new(),
         }
     }
+
+    pub fn used_types(&self) -> impl Iterator<Item = &Type> {
+        self.types.iter().map(Rc::as_ref)
+    }
+
     /// Adds all dependencies from the given type
     pub fn append_from(&mut self, ty: &Type) {
-        let crate_rename = &self.crate_rename;
-        self.dependencies
-            .push(quote![.extend(<#ty as #crate_rename::TS>::dependency_types())]);
-        self.types.push(ty.clone());
+        let ty = self.push_type(ty);
+        self.dependencies.insert(Dependency::Transitive {
+            crate_rename: self.crate_rename.clone(),
+            ty: ty.clone(),
+        });
     }
 
     /// Adds the given type.
     pub fn push(&mut self, ty: &Type) {
-        let crate_rename = &self.crate_rename;
-        self.dependencies.push(quote![.push::<#ty>()]);
-        self.dependencies.push(quote![
-            .extend(<#ty as #crate_rename::TS>::generics())
-        ]);
-        self.types.push(ty.clone());
+        let ty = self.push_type(ty);
+        self.dependencies.insert(Dependency::Type(ty.clone()));
+        self.dependencies.insert(Dependency::Generics {
+            crate_rename: self.crate_rename.clone(),
+            ty: ty.clone(),
+        });
     }
 
-    pub fn append(&mut self, mut other: Dependencies) {
-        if !other.dependencies.is_empty() {
-            self.dependencies.push(quote![.extend(#other)]);
+    pub fn append(&mut self, other: Dependencies) {
+        self.dependencies.extend(other.dependencies);
+        self.types.extend(other.types);
+    }
+
+    fn push_type(&mut self, ty: &Type) -> Rc<Type> {
+        // this can be replaces with `get_or_insert_owned` once #60896 is stabilized
+        match self.types.get(ty) {
+            None => {
+                let ty = Rc::new(ty.clone());
+                self.types.insert(ty.clone());
+                ty
+            }
+            Some(ty) => ty.clone(),
         }
-        self.types.append(&mut other.types);
     }
 }
 
 impl ToTokens for Dependencies {
     fn to_tokens(&self, tokens: &mut TokenStream) {
         let crate_rename = &self.crate_rename;
-        let lines = &self.dependencies;
+        let lines = self.dependencies.iter();
+
         tokens.extend(quote![{
             use #crate_rename::typelist::TypeList;
             ()#(#lines)*
-        }])
+        }]);
+    }
+}
+
+impl ToTokens for Dependency {
+    fn to_tokens(&self, tokens: &mut TokenStream) {
+        tokens.extend(match self {
+            Dependency::Transitive { crate_rename, ty } => {
+                quote![.extend(<#ty as #crate_rename::TS>::dependency_types())]
+            }
+            Dependency::Generics { crate_rename, ty } => {
+                quote![.extend(<#ty as #crate_rename::TS>::generics())]
+            }
+            Dependency::Type(ty) => quote![.push::<#ty>()],
+        });
     }
 }
diff --git a/macros/src/lib.rs b/macros/src/lib.rs
index b4895d52..8ec15668 100644
--- a/macros/src/lib.rs
+++ b/macros/src/lib.rs
@@ -368,7 +368,7 @@ fn generate_where_clause(
         let is_type_param = |id: &Ident| generics.type_params().any(|p| &p.ident == id);
 
         let mut used_types = HashSet::new();
-        for ty in &dependencies.types {
+        for ty in dependencies.used_types() {
             used_type_params(&mut used_types, ty, is_type_param);
         }
         used_types.into_iter()
diff --git a/ts-rs/tests/recursion_limit.rs b/ts-rs/tests/recursion_limit.rs
index f859023f..1f0f98ae 100644
--- a/ts-rs/tests/recursion_limit.rs
+++ b/ts-rs/tests/recursion_limit.rs
@@ -1,170 +1,82 @@
+use std::any::TypeId;
+
+use ts_rs::{
+    typelist::{TypeList, TypeVisitor},
+    TS,
+};
+
+#[rustfmt::skip]
 #[derive(Debug, ts_rs::TS)]
-#[ts(export)]
+#[ts(export, export_to = "very_big_types/")]
 pub enum Iso4217CurrencyCode {
-    AED,
-    AFN,
-    ALL,
-    AMD,
-    ANG,
-    AOA,
-    ARS,
-    AUD,
-    AWG,
-    AZN,
-    BAM,
-    BBD,
-    BDT,
-    BGN,
-    BHD,
-    BIF,
-    BMD,
-    BND,
-    BOB,
-    BRL,
-    BSD,
-    BTN,
-    BWP,
-    BYN,
-    BZD,
-    CAD,
-    CDF,
-    CHF,
-    CLP,
-    CNY,
-    COP,
-    CRC,
-    CUC,
-    CUP,
-    CVE,
-    CZK,
-    DJF,
-    DKK,
-    DOP,
-    DZD,
-    EGP,
-    ERN,
-    ETB,
-    EUR,
-    FJD,
-    FKP,
-    GBP,
-    GEL,
-    GGP,
-    GHS,
-    GIP,
-    GMD,
-    GNF,
-    GTQ,
-    GYD,
-    HKD,
-    HNL,
-    HRK,
-    HTG,
-    HUF,
-    IDR,
-    ILS,
-    IMP,
-    INR,
-    IQD,
-    IRR,
-    ISK,
-    JEP,
-    JMD,
-    JOD,
-    JPY,
-    KES,
-    KGS,
-    KHR,
-    KMF,
-    KPW,
-    KRW,
-    KWD,
-    KYD,
-    KZT,
-    LAK,
-    LBP,
-    LKR,
-    LRD,
-    LSL,
-    LYD,
-    MAD,
-    MDL,
-    MGA,
-    MKD,
-    MMK,
-    MNT,
-    MOP,
-    MRU,
-    MUR,
-    MVR,
-    MWK,
-    MXN,
-    MYR,
-    MZN,
-    NAD,
-    NGN,
-    NIO,
-    NOK,
-    NPR,
-    NZD,
-    OMR,
-    PAB,
-    PEN,
-    PGK,
-    PHP,
-    PKR,
-    PLN,
-    PYG,
-    QAR,
-    RON,
-    RSD,
-    RUB,
-    RWF,
-    SAR,
-    SBD,
-    SCR,
-    SDG,
-    SEK,
-    SGD,
-    SHP,
-    SLL,
-    SOS,
-    SPL,
-    SRD,
-    STN,
-    SVC,
-    SYP,
-    SZL,
-    THB,
-    TJS,
-    TMT,
-    TND,
-    TOP,
-    TRY,
-    TTD,
-    TVD,
-    TWD,
-    TZS,
-    UAH,
-    UGX,
-    USD,
-    UYU,
-    UZS,
-    VEF,
-    VND,
-    VUV,
-    WST,
-    XAF,
-    XCD,
-    XDR,
-    XOF,
-    XPF,
-    YER,
-    ZAR,
-    ZMW,
-    ZWD,
+    AED, AFN, ALL, AMD, ANG, AOA, ARS, AUD, AWG, AZN, BAM, BBD, BDT, BGN, BHD, BIF, BMD, BND, BOB,
+    BRL, BSD, BTN, BWP, BYN, BZD, CAD, CDF, CHF, CLP, CNY, COP, CRC, CUC, CUP, CVE, CZK, DJF, DKK,
+    DOP, DZD, EGP, ERN, ETB, EUR, FJD, FKP, GBP, GEL, GGP, GHS, GIP, GMD, GNF, GTQ, GYD, HKD, HNL, 
+    HRK, HTG, HUF, IDR, ILS, IMP, INR, IQD, IRR, ISK, JEP, JMD, JOD, JPY, KES, KGS, KHR, KMF, KPW, 
+    KRW, KWD, KYD, KZT, LAK, LBP, LKR, LRD, LSL, LYD, MAD, MDL, MGA, MKD, MMK, MNT, MOP, MRU, MUR,
+    MVR, MWK, MXN, MYR, MZN, NAD, NGN, NIO, NOK, NPR, NZD, OMR, PAB, PEN, PGK, PHP, PKR, PLN, PYG,
+    QAR, RON, RSD, RUB, RWF, SAR, SBD, SCR, SDG, SEK, SGD, SHP, SLL, SOS, SPL, SRD, STN, SVC, SYP,
+    SZL, THB, TJS, TMT, TND, TOP, TRY, TTD, TVD, TWD, TZS, UAH, UGX, USD, UYU, UZS, VEF, VND, VUV, 
+    WST, XAF, XCD, XDR, XOF, XPF, YER, ZAR, ZMW, ZWD,
+}
+
+#[rustfmt::skip]
+#[derive(Debug, ts_rs::TS)]
+#[ts(export, export_to = "very_big_types/")]
+pub enum VeryBigEnum {
+    V001(String), V002(String), V003(String), V004(String), V005(String), V006(String), V007(String),
+    V008(String), V009(String), V010(String), V011(String), V012(String), V013(String), V014(String),
+    V015(String), V016(String), V017(String), V018(String), V019(String), V020(String), V021(String),
+    V022(String), V023(String), V024(String), V025(String), V026(String), V027(String), V028(String),
+    V029(String), V030(String), V031(String), V032(String), V033(String), V034(String), V035(String),
+    V036(String), V037(String), V038(String), V039(String), V040(String), V041(String), V042(String),
+    V043(String), V044(String), V045(String), V046(String), V047(String), V048(String), V049(String),
+    V050(String), V051(String), V052(String), V053(String), V054(String), V055(String), V056(String),
+    V057(String), V058(String), V059(String), V060(String), V061(String), V062(String), V063(String),
+    V064(String), V065(String), V066(String), V067(String), V068(String), V069(String), V070(String),
+    V071(String), V072(String), V073(String), V074(String), V075(String), V076(String), V077(String),
+    V078(String), V079(String), V080(String), V081(String), V082(String), V083(String), V084(String),
+    V085(String), V086(String), V087(String), V088(String), V089(String), V090(String), V091(String),
+    V092(String), V093(String), V094(String), V095(String), V096(String), V097(String), V098(String),
+    V099(String), V100(String), V101(String), V102(String), V103(String), V104(String), V105(String),
+    V106(String), V107(String), V108(String), V109(String), V110(String), V111(String), V112(String),
+    V113(String), V114(String), V115(String), V116(String), V117(String), V118(String), V119(String),
+    V120(String), V121(String), V122(String), V123(String), V124(String), V125(String), V126(String),
+    V127(String), V128(String), V129(String), V130(String), V131(String), V132(String), V133(String),
+    V134(String), V135(String), V136(String), V137(String), V138(String), V139(String), V140(String),
+    V141(String), V142(String), V143(String), V144(String), V145(String), V146(String), V147(String),
+    V148(String), V149(String), V150(String), V151(String), V152(String), V153(String), V154(String),
+    V155(String), V156(String), V157(String), V158(String), V159(String), V160(String), V161(String),
+    V162(String), V163(String), V164(String), V165(String), V166(String), V167(String), V168(String),
+    V169(String), V170(String), V171(String), V172(String), V173(String), V174(String), V175(String),
+    V176(String), V177(String), V178(String), V179(String), V180(String), V181(String), V182(String),
+    V183(String), V184(String), V185(String), V186(String), V187(String), V188(String), V189(String),
+    V190(String), V191(String), V192(String), V193(String), V194(String), V195(String), V196(String),
+    V197(String), V198(String), V199(String), V200(String), V201(String), V202(String), V203(String),
+    V204(String), V205(String), V206(String), V207(String), V208(String), V209(String), V210(String),
+    V211(String), V212(String), V213(String), V214(String), V215(String), V216(String), V217(String),
+    V218(String), V219(String), V220(String), V221(String), V222(String), V223(String), V224(String),
+    V225(String), V226(String), V227(String), V228(String), V229(String), V230(String), V231(String),
+    V232(String), V233(String), V234(String), V235(String), V236(String), V237(String), V238(String),
+    V239(String), V240(String), V241(String), V242(String), V243(String), V244(String), V245(String),
+    V246(String), V247(String), V248(String), V249(String), V250(String), V251(String), V252(String),
+    V253(String), V254(String), V255(String), V256(String), 
 }
 
-fn main() {
-    println!("{:?}", Iso4217CurrencyCode::USD)
+#[test]
+fn very_big_enum() {
+    struct Visitor(bool);
+
+    impl TypeVisitor for Visitor {
+        fn visit<T: TS + 'static + ?Sized>(&mut self) {
+            assert!(!self.0, "there must only be one dependency");
+            assert_eq!(TypeId::of::<T>(), TypeId::of::<String>());
+            self.0 = true;
+        }
+    }
+
+    let mut visitor = Visitor(false);
+    VeryBigEnum::dependency_types().for_each(&mut visitor);
+
+    assert!(visitor.0, "there must be at least one dependency");
 }