diff --git a/tests/testsuite/artifact_dep.rs b/tests/testsuite/artifact_dep.rs
index 5f33a43d720f..e4806a084405 100644
--- a/tests/testsuite/artifact_dep.rs
+++ b/tests/testsuite/artifact_dep.rs
@@ -2672,3 +2672,259 @@ fn same_target_transitive_dependency_deduplication_lib() {
         )
         .run();
 }
+
+#[cargo_test]
+fn issue_10525() {
+    let p = project()
+        .file(
+            "Cargo.toml",
+            r#"
+            [package]
+            name = "mycrate"
+            version = "0.0.0"
+            edition = "2021"
+
+            [dependencies]
+            structopt-derive = { path = "structopt-derive" }
+            mybindep = { path = "mybindep", artifact = "bin", target = "x86_64-unknown-linux-gnu" }
+            "#,
+        )
+        .file(
+            "src/main.rs",
+            r#"
+            fn main() {
+                env!("CARGO_BIN_FILE_MYBINDEP");
+            }
+            "#,
+        )
+        .file(
+            "mybindep/Cargo.toml",
+            r#"
+            [package]
+            name = "mybindep"
+            version = "0.0.0"
+            edition = "2021"
+
+            [dependencies]
+            clap_derive = { path = "../clap_derive" }
+            "#,
+        )
+        .file("mybindep/src/main.rs", "fn main() {}")
+        .file(
+            "clap_derive/Cargo.toml",
+            r#"
+            [package]
+            name = "clap_derive"
+            version = "0.0.0"
+            edition = "2021"
+
+            [dependencies]
+            proc-macro-error = { path = "../proc-macro-error" }
+
+            [lib]
+            proc-macro = true
+            "#,
+        )
+        .file("clap_derive/src/lib.rs", "")
+        .file(
+            "structopt-derive/Cargo.toml",
+            r#"
+            [package]
+            name = "structopt-derive"
+            version = "0.0.0"
+            edition = "2021"
+
+            [dependencies]
+            syn = { path = "../syn", features = ["parsing"] }
+            proc-macro-error = { path = "../proc-macro-error" }
+
+            [lib]
+            proc-macro = true
+            "#,
+        )
+        .file(
+            "structopt-derive/src/lib.rs",
+            r#"
+            use proc_macro_error::ResultExt;
+
+            fn _parse_structopt_attributes() {
+                Ok::<(), syn::Error>(()).unwrap_or_abort()
+            }
+            "#,
+        )
+        .file(
+            "proc-macro-error/Cargo.toml",
+            r#"
+            [package]
+            name = "proc-macro-error"
+            version = "0.0.0"
+            edition = "2021"
+
+            [dependencies]
+            syn = { path = "../syn" }
+            "#,
+        )
+        .file(
+            "proc-macro-error/src/lib.rs",
+            r#"
+            pub trait ResultExt<T> {
+                fn unwrap_or_abort(self) -> T;
+            }
+
+            impl<T, E: Into<Diagnostic>> ResultExt<T> for Result<T, E> {
+                fn unwrap_or_abort(self) -> T {
+                    panic!()
+                }
+            }
+
+            pub struct Diagnostic;
+
+            impl From<syn::Error> for Diagnostic {
+                fn from(_: syn::Error) -> Self {
+                    panic!()
+                }
+            }
+            "#,
+        )
+        .file(
+            "syn/Cargo.toml",
+            r#"
+            [package]
+            name = "syn"
+            version = "0.0.0"
+            edition = "2021"
+
+            [features]
+            parsing = []
+            "#,
+        )
+        .file("syn/src/lib.rs", "pub struct Error;")
+        .build();
+
+    p.cargo("build -Z bindeps")
+        .masquerade_as_nightly_cargo(&["bindeps"])
+        .with_stderr_unordered(
+            "\
+[COMPILING] mycrate v0.0.0 ([CWD])
+[COMPILING] mybindep v0.0.0 ([CWD]/mybindep)
+[COMPILING] clap_derive v0.0.0 ([CWD]/clap_derive)
+[COMPILING] structopt-derive v0.0.0 ([CWD]/structopt-derive)
+[COMPILING] proc-macro-error v0.0.0 ([CWD]/proc-macro-error)
+[COMPILING] syn v0.0.0 ([CWD]/syn)
+[FINISHED] dev [..]
+",
+        )
+        .run();
+}
+
+#[cargo_test]
+fn issue_10837() {
+    let p = project()
+        .file(
+            "Cargo.toml",
+            r#"
+            [package]
+            name = "mycrate"
+            version = "0.0.0"
+            edition = "2021"
+
+            [dependencies]
+            indexmap = { path = "indexmap" }
+            serde = { path = "serde", features = ["alloc"] }
+            wasmtime-environ = { path = "wasmtime-environ", lib = true, artifact = "bin", target = "x86_64-unknown-linux-gnu" }
+            "#,
+        )
+        .file("src/lib.rs", "")
+        .file(
+            "indexmap/Cargo.toml",
+            r#"
+            [package]
+            name = "indexmap"
+            version = "0.0.0"
+            edition = "2021"
+
+            [dependencies]
+            serde = { path = "../serde", optional = true }
+            "#,
+        )
+        .file(
+            "indexmap/src/lib.rs",
+            r#"
+            pub struct IndexMap;
+
+            #[cfg(feature = "serde")]
+            impl serde::Serialize for IndexMap {
+                fn serialize<T: serde::Serializer>(&self, _: T) {}
+            }
+            "#,
+        )
+        .file(
+            "serde/Cargo.toml",
+            r#"
+            [package]
+            name = "serde"
+            version = "0.0.0"
+            edition = "2021"
+
+            [features]
+            alloc = []
+            "#,
+        )
+        .file(
+            "serde/src/lib.rs",
+            r#"
+            pub trait Serialize {
+                fn serialize<S: Serializer>(&self, serializer: S);
+            }
+
+            pub trait Serializer {
+                fn serialize_field<T: Serialize>(&self, value: &T);
+            }
+            "#,
+        )
+        .file(
+            "wasmtime-environ/Cargo.toml",
+            r#"
+            [package]
+            name = "wasmtime-environ"
+            version = "0.0.0"
+            edition = "2021"
+
+            [dependencies]
+            indexmap = { path = "../indexmap", features = ["serde"] }
+            serde = { path = "../serde" }
+            "#,
+        )
+        .file(
+            "wasmtime-environ/src/lib.rs",
+            r#"
+            use indexmap::IndexMap;
+            use serde::{Serialize, Serializer};
+
+            struct Module {
+                exports: IndexMap,
+            }
+
+            impl Serialize for Module {
+                fn serialize<T: Serializer>(&self, serializer: T) {
+                    serializer.serialize_field(&self.exports);
+                }
+            }
+            "#,
+        )
+        .file("wasmtime-environ/src/main.rs", "fn main() {}")
+        .build();
+
+    p.cargo("build -Z bindeps")
+        .masquerade_as_nightly_cargo(&["bindeps"])
+        .with_stderr_unordered(
+            "\
+[COMPILING] mycrate v0.0.0 ([CWD])
+[COMPILING] indexmap v0.0.0 ([CWD]/indexmap)
+[COMPILING] serde v0.0.0 ([CWD]/serde)
+[COMPILING] wasmtime-environ v0.0.0 ([CWD]/wasmtime-environ)
+[FINISHED] dev [..]
+",
+        )
+        .run();
+}