diff --git a/src/bootstrap/src/core/config/target_selection.rs b/src/bootstrap/src/core/config/target_selection.rs
new file mode 100644
index 000000000000..ebd3fe7a8c68
--- /dev/null
+++ b/src/bootstrap/src/core/config/target_selection.rs
@@ -0,0 +1,147 @@
+use std::fmt;
+
+use crate::core::config::SplitDebuginfo;
+use crate::utils::cache::{INTERNER, Interned};
+use crate::{Path, env};
+
+#[derive(Copy, Clone, Default, PartialEq, Eq, PartialOrd, Ord, Hash)]
+// N.B.: This type is used everywhere, and the entire codebase relies on it being Copy.
+// Making !Copy is highly nontrivial!
+pub struct TargetSelection {
+    pub triple: Interned<String>,
+    pub file: Option<Interned<String>>,
+    pub synthetic: bool,
+}
+
+/// Newtype over `Vec<TargetSelection>` so we can implement custom parsing logic
+#[derive(Clone, Default, PartialEq, Eq, PartialOrd, Ord, Hash, Debug)]
+pub struct TargetSelectionList(pub Vec<TargetSelection>);
+
+pub fn target_selection_list(s: &str) -> Result<TargetSelectionList, String> {
+    Ok(TargetSelectionList(
+        s.split(',').filter(|s| !s.is_empty()).map(TargetSelection::from_user).collect(),
+    ))
+}
+
+impl TargetSelection {
+    pub fn from_user(selection: &str) -> Self {
+        let path = Path::new(selection);
+
+        let (triple, file) = if path.exists() {
+            let triple = path
+                .file_stem()
+                .expect("Target specification file has no file stem")
+                .to_str()
+                .expect("Target specification file stem is not UTF-8");
+
+            (triple, Some(selection))
+        } else {
+            (selection, None)
+        };
+
+        let triple = INTERNER.intern_str(triple);
+        let file = file.map(|f| INTERNER.intern_str(f));
+
+        Self { triple, file, synthetic: false }
+    }
+
+    pub fn create_synthetic(triple: &str, file: &str) -> Self {
+        Self {
+            triple: INTERNER.intern_str(triple),
+            file: Some(INTERNER.intern_str(file)),
+            synthetic: true,
+        }
+    }
+
+    pub fn rustc_target_arg(&self) -> &str {
+        self.file.as_ref().unwrap_or(&self.triple)
+    }
+
+    pub fn contains(&self, needle: &str) -> bool {
+        self.triple.contains(needle)
+    }
+
+    pub fn starts_with(&self, needle: &str) -> bool {
+        self.triple.starts_with(needle)
+    }
+
+    pub fn ends_with(&self, needle: &str) -> bool {
+        self.triple.ends_with(needle)
+    }
+
+    // See src/bootstrap/synthetic_targets.rs
+    pub fn is_synthetic(&self) -> bool {
+        self.synthetic
+    }
+
+    pub fn is_msvc(&self) -> bool {
+        self.contains("msvc")
+    }
+
+    pub fn is_windows(&self) -> bool {
+        self.contains("windows")
+    }
+
+    pub fn is_windows_gnu(&self) -> bool {
+        self.ends_with("windows-gnu")
+    }
+
+    pub fn is_cygwin(&self) -> bool {
+        self.is_windows() &&
+        // ref. https://cygwin.com/pipermail/cygwin/2022-February/250802.html
+        env::var("OSTYPE").is_ok_and(|v| v.to_lowercase().contains("cygwin"))
+    }
+
+    pub fn needs_crt_begin_end(&self) -> bool {
+        self.contains("musl") && !self.contains("unikraft")
+    }
+
+    /// Path to the file defining the custom target, if any.
+    pub fn filepath(&self) -> Option<&Path> {
+        self.file.as_ref().map(Path::new)
+    }
+}
+
+impl fmt::Display for TargetSelection {
+    fn fmt(&self, f: &mut fmt::Formatter<'_>) -> fmt::Result {
+        write!(f, "{}", self.triple)?;
+        if let Some(file) = self.file {
+            write!(f, "({file})")?;
+        }
+        Ok(())
+    }
+}
+
+impl fmt::Debug for TargetSelection {
+    fn fmt(&self, f: &mut fmt::Formatter<'_>) -> fmt::Result {
+        write!(f, "{self}")
+    }
+}
+
+impl PartialEq<&str> for TargetSelection {
+    fn eq(&self, other: &&str) -> bool {
+        self.triple == *other
+    }
+}
+
+// Targets are often used as directory names throughout bootstrap.
+// This impl makes it more ergonomics to use them as such.
+impl AsRef<Path> for TargetSelection {
+    fn as_ref(&self) -> &Path {
+        self.triple.as_ref()
+    }
+}
+
+impl SplitDebuginfo {
+    /// Returns the default `-Csplit-debuginfo` value for the current target. See the comment for
+    /// `rust.split-debuginfo` in `bootstrap.example.toml`.
+    pub fn default_for_platform(target: TargetSelection) -> Self {
+        if target.contains("apple") {
+            SplitDebuginfo::Unpacked
+        } else if target.is_windows() {
+            SplitDebuginfo::Packed
+        } else {
+            SplitDebuginfo::Off
+        }
+    }
+}