diff --git a/src/bootstrap/src/core/build_steps/llvm.rs b/src/bootstrap/src/core/build_steps/llvm.rs
index 087a395a067f0..b3ae5bfbd74f2 100644
--- a/src/bootstrap/src/core/build_steps/llvm.rs
+++ b/src/bootstrap/src/core/build_steps/llvm.rs
@@ -166,10 +166,16 @@ pub fn prebuilt_llvm_config(
 
     static STAMP_HASH_MEMO: OnceLock<String> = OnceLock::new();
     let smart_stamp_hash = STAMP_HASH_MEMO.get_or_init(|| {
+        // Key LLVM on the commit hash and the configuration from bootstrap.toml.
+        let hash_input = format!(
+            "sha={sha}\nkey={key}",
+            sha = builder.in_tree_llvm_info.sha().unwrap_or_default(),
+            key = builder.config.llvm_cache_key,
+        );
         generate_smart_stamp_hash(
             builder,
             &builder.config.src.join("src/llvm-project"),
-            builder.in_tree_llvm_info.sha().unwrap_or_default(),
+            &hash_input,
         )
     });
 
diff --git a/src/bootstrap/src/core/config/config.rs b/src/bootstrap/src/core/config/config.rs
index 5a9c7264c006f..0297907057ef9 100644
--- a/src/bootstrap/src/core/config/config.rs
+++ b/src/bootstrap/src/core/config/config.rs
@@ -156,6 +156,9 @@ pub struct Config {
     pub backtrace_on_ice: bool,
 
     // llvm codegen options
+    /// Key used to decide when to rebuild LLVM.
+    pub llvm_cache_key: String,
+
     pub llvm_assertions: bool,
     pub llvm_tests: bool,
     pub llvm_enzyme: bool,
@@ -595,6 +598,8 @@ impl Config {
             rustflags: rust_rustflags,
         } = toml.rust.unwrap_or_default();
 
+        let llvm = toml.llvm.unwrap_or_default();
+        let llvm_cache_key = llvm.cache_key();
         let Llvm {
             optimize: llvm_optimize,
             thin_lto: llvm_thin_lto,
@@ -625,7 +630,7 @@ impl Config {
             enable_warnings: llvm_enable_warnings,
             download_ci_llvm: llvm_download_ci_llvm,
             build_config: llvm_build_config,
-        } = toml.llvm.unwrap_or_default();
+        } = llvm;
 
         let Dist {
             sign_folder: dist_sign_folder,
@@ -1401,6 +1406,7 @@ impl Config {
             llvm_assertions,
             llvm_bitcode_linker_enabled: rust_llvm_bitcode_linker.unwrap_or(false),
             llvm_build_config: llvm_build_config.clone().unwrap_or(Default::default()),
+            llvm_cache_key,
             llvm_cflags,
             llvm_clang: llvm_clang.unwrap_or(false),
             llvm_clang_cl,
diff --git a/src/bootstrap/src/core/config/toml/llvm.rs b/src/bootstrap/src/core/config/toml/llvm.rs
index 5f08884e4ef71..ad5db7ebe870d 100644
--- a/src/bootstrap/src/core/config/toml/llvm.rs
+++ b/src/bootstrap/src/core/config/toml/llvm.rs
@@ -43,6 +43,95 @@ define_config! {
     }
 }
 
+impl Llvm {
+    /// A key that is used to determine whether LLVM should be rebuilt.
+    pub(crate) fn cache_key(&self) -> String {
+        let helper = || {
+            let mut key = String::with_capacity(512);
+
+            let Self {
+                optimize,
+                thin_lto,
+                release_debuginfo,
+                assertions,
+                tests,
+                enzyme,
+                plugins,
+                static_libstdcpp,
+                libzstd,
+                ninja,
+                targets,
+                experimental_targets,
+                link_jobs,
+                link_shared,
+                version_suffix,
+                clang_cl,
+                cflags,
+                cxxflags,
+                ldflags,
+                use_libcxx,
+                use_linker,
+                allow_old_toolchain,
+                offload,
+                polly,
+                offload_clang_dir,
+                clang,
+                enable_warnings,
+                build_config,
+                download_ci_llvm: _,
+            } = self;
+
+            use std::fmt::Write;
+            write!(key, "{:?}", optimize)?;
+            write!(key, "{:?}", thin_lto)?;
+            write!(key, "{:?}", release_debuginfo)?;
+            write!(key, "{:?}", assertions)?;
+            write!(key, "{:?}", tests)?;
+            write!(key, "{:?}", enzyme)?;
+            write!(key, "{:?}", plugins)?;
+            write!(key, "{:?}", static_libstdcpp)?;
+            write!(key, "{:?}", libzstd)?;
+            write!(key, "{:?}", ninja)?;
+            write!(key, "{:?}", targets)?;
+            write!(key, "{:?}", experimental_targets)?;
+            write!(key, "{:?}", link_jobs)?;
+            write!(key, "{:?}", link_shared)?;
+            write!(key, "{:?}", version_suffix)?;
+            write!(key, "{:?}", clang_cl)?;
+            write!(key, "{:?}", cflags)?;
+            write!(key, "{:?}", cxxflags)?;
+            write!(key, "{:?}", ldflags)?;
+            write!(key, "{:?}", use_libcxx)?;
+            write!(key, "{:?}", use_linker)?;
+            write!(key, "{:?}", allow_old_toolchain)?;
+            write!(key, "{:?}", offload)?;
+            write!(key, "{:?}", polly)?;
+            write!(key, "{:?}", offload_clang_dir)?;
+            write!(key, "{:?}", clang)?;
+            write!(key, "{:?}", enable_warnings)?;
+
+            match build_config {
+                None => {
+                    write!(key, "None")?;
+                }
+                Some(c) => {
+                    let mut build_config = c.iter().collect::<Vec<_>>();
+                    build_config.sort();
+
+                    for (k, v) in build_config {
+                        write!(key, "{}: {}", k, v)?;
+                    }
+                }
+            }
+
+            Ok::<_, std::fmt::Error>(key)
+        };
+
+        // write! to a String always succeeds unless OOM.
+        helper().unwrap()
+    }
+}
+
 /// Compares the current `Llvm` options against those in the CI LLVM builder and detects any incompatible options.
 /// It does this by destructuring the `Llvm` instance to make sure every `Llvm` field is covered and not missing.
 #[cfg(not(test))]