diff --git a/.github/workflows/test-windows-trampolines.yml b/.github/workflows/test-windows-trampolines.yml
index 0bdbc1c53..06a1a4267 100644
--- a/.github/workflows/test-windows-trampolines.yml
+++ b/.github/workflows/test-windows-trampolines.yml
@@ -25,6 +25,25 @@ jobs:
       - name: "Check windows crate versions match"
         run: uv run --no-project scripts/check-trampoline-version-consistency.py
 
+  # Verify committed trampolines match a reproducible Docker build
+  windows-trampoline-reproducible:
+    timeout-minutes: 30
+    runs-on: ubuntu-latest
+    name: "check reproducible build"
+    steps:
+      - uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2
+        with:
+          persist-credentials: false
+
+      - name: "Set up Docker Buildx"
+        uses: docker/setup-buildx-action@b5ca514318bd6ebac0fb2aedd5d36ec1b5c232a2 # v3.10.0
+
+      - name: "Build trampolines in Docker"
+        run: scripts/build-trampolines.sh --cache-from type=gha --cache-to type=gha
+
+      - name: "Check committed trampolines match build"
+        run: git diff --exit-code crates/uv-trampoline-builder/trampolines/
+
   # Separate jobs for the nightly crate
   windows-trampoline-check:
     timeout-minutes: 15
diff --git a/Cargo.lock b/Cargo.lock
index ac122a397..c81a71ceb 100644
--- a/Cargo.lock
+++ b/Cargo.lock
@@ -7387,6 +7387,7 @@ dependencies = [
  "assert_cmd",
  "assert_fs",
  "fs-err",
+ "goblin",
  "rcgen",
  "tempfile",
  "thiserror 2.0.18",
diff --git a/Cargo.toml b/Cargo.toml
index 7a74b7eb3..cfb1c2a84 100644
--- a/Cargo.toml
+++ b/Cargo.toml
@@ -157,6 +157,8 @@ goblin = { version = "0.10.0", default-features = false, features = [
   "elf32",
   "elf64",
   "endian_fd",
+  "pe32",
+  "pe64",
 ] }
 h2 = { version = "0.4.7" }
 hashbrown = { version = "0.16.0" }
diff --git a/crates/uv-trampoline-builder/Cargo.toml b/crates/uv-trampoline-builder/Cargo.toml
index d8d2acc6e..0cd730a16 100644
--- a/crates/uv-trampoline-builder/Cargo.toml
+++ b/crates/uv-trampoline-builder/Cargo.toml
@@ -20,10 +20,15 @@ production = []
 [lints]
 workspace = true
 
+[[bin]]
+name = "normalize-pe-timestamps"
+
 [dependencies]
 uv-fs = { workspace = true }
 
-fs-err = { workspace = true }
+anyhow = {workspace = true }
+fs-err = {workspace = true }
+goblin = { workspace = true }
 tempfile = { workspace = true }
 thiserror = { workspace = true }
 zip = { workspace = true }
diff --git a/crates/uv-trampoline-builder/src/bin/normalize-pe-timestamps.rs b/crates/uv-trampoline-builder/src/bin/normalize-pe-timestamps.rs
new file mode 100644
index 000000000..d5e316aca
--- /dev/null
+++ b/crates/uv-trampoline-builder/src/bin/normalize-pe-timestamps.rs
@@ -0,0 +1,110 @@
+//! Zero out non-deterministic fields in PE executables.
+//!
+//! Even with the `/Brepro`, the PE timestamp and debug directory GUID change
+//! between builds. We have to zero out those fields so the final binaries are
+//! byte-for-byte reproducible.
+//!
+//! Fields zeroed:
+//! - COFF header `TimeDateStamp`
+//! - Each `IMAGE_DEBUG_DIRECTORY` `TimeDateStamp`
+//! - `CodeView` PDB70 `Signature` (GUID) and `Age`
+
+use std::env;
+
+use anyhow::{Context, Result, bail, format_err};
+use goblin::pe::PE;
+use goblin::pe::debug::{IMAGE_DEBUG_TYPE_CODEVIEW, ImageDebugDirectory};
+use goblin::pe::section_table::SectionTable;
+use uv_fs::Simplified;
+
+/// Collected fixup locations from the PE parse.
+struct DebugEntryFixup {
+    /// File offset of this `IMAGE_DEBUG_DIRECTORY` entry.
+    entry_file_offset: usize,
+    /// The `IMAGE_DEBUG_DIRECTORY.data_type` field.
+    data_type: u32,
+    /// The `IMAGE_DEBUG_DIRECTORY.pointer_to_raw_data` field (file offset of the payload).
+    pointer_to_raw_data: u32,
+}
+
+/// Resolve an RVA to a file offset using the PE section table.
+fn rva_to_file_offset(sections: &[SectionTable], rva: u32) -> Option<usize> {
+    sections.iter().find_map(|section| {
+        if rva >= section.virtual_address && rva < section.virtual_address + section.virtual_size {
+            Some((rva - section.virtual_address + section.pointer_to_raw_data) as usize)
+        } else {
+            None
+        }
+    })
+}
+
+fn parse_debug_entries(data: &mut [u8]) -> Result<(usize, Vec<DebugEntryFixup>)> {
+    let pe = PE::parse(data)?;
+
+    // COFF header: pe_pointer -> "PE\0\0" (4 bytes) -> CoffHeader fields.
+    // `CoffHeader.time_date_stamp` is the second u32 field (offset 4).
+    let coff_timestamp_offset = pe.header.dos_header.pe_pointer as usize + 4 + 4;
+
+    let mut debug_entries = Vec::new();
+    if let Some(debug_data_directory) = pe
+        .header
+        .optional_header
+        .and_then(|opt| opt.data_directories.get_debug_table().copied())
+    {
+        if let Some(debug_data) = &pe.debug_data {
+            let debug_dir_file_offset =
+                rva_to_file_offset(&pe.sections, debug_data_directory.virtual_address)
+                    .ok_or_else(|| format_err!("cannot resolve debug directory RVA"))?;
+            let entry_size = size_of::<ImageDebugDirectory>();
+
+            for (i, entry) in debug_data.entries().enumerate() {
+                let entry = entry?;
+                debug_entries.push(DebugEntryFixup {
+                    entry_file_offset: debug_dir_file_offset + i * entry_size,
+                    data_type: entry.data_type,
+                    pointer_to_raw_data: entry.pointer_to_raw_data,
+                });
+            }
+        }
+    }
+
+    Ok((coff_timestamp_offset, debug_entries))
+}
+
+fn clear_debug_entries(
+    data: &mut [u8],
+    coff_timestamp_offset: usize,
+    debug_entries: &[DebugEntryFixup],
+) {
+    // Zero COFF header `TimeDateStamp`.
+    data[coff_timestamp_offset..coff_timestamp_offset + 4].fill(0);
+
+    // Zero debug directory timestamps and CodeView GUIDs.
+    for entry in debug_entries {
+        // Zero `IMAGE_DEBUG_DIRECTORY.time_date_stamp` (offset 4 in the struct).
+        let timestamp_offset = entry.entry_file_offset + 4;
+        data[timestamp_offset..timestamp_offset + 4].fill(0);
+
+        if entry.data_type == IMAGE_DEBUG_TYPE_CODEVIEW {
+            // PDB70 layout: magic[4] ("RSDS") | guid[16] | age[4] | filename...
+            let payload = entry.pointer_to_raw_data as usize;
+            data[payload + 4..payload + 20].fill(0); // Signature (GUID)
+            data[payload + 20..payload + 24].fill(0); // Age
+        }
+    }
+}
+
+fn main() -> Result<()> {
+    let args: Vec<String> = env::args().collect();
+    if args.len() < 2 {
+        bail!("Usage: {} <file.exe> [...]", args[0]);
+    }
+    for path in &args[1..] {
+        let mut data = fs_err::read(path)?;
+        let (coff_timestamp_offset, debug_entries) = parse_debug_entries(&mut data)
+            .with_context(|| format!("Failed to normalize: {}", path.user_display()))?;
+        clear_debug_entries(&mut data, coff_timestamp_offset, &debug_entries);
+        fs_err::write(path, &data)?;
+    }
+    Ok(())
+}
diff --git a/crates/uv-trampoline-builder/trampolines/uv-trampoline-aarch64-console.exe b/crates/uv-trampoline-builder/trampolines/uv-trampoline-aarch64-console.exe
index e5449cee8..a9cbc2d3b 100755
Binary files a/crates/uv-trampoline-builder/trampolines/uv-trampoline-aarch64-console.exe and b/crates/uv-trampoline-builder/trampolines/uv-trampoline-aarch64-console.exe differ
diff --git a/crates/uv-trampoline-builder/trampolines/uv-trampoline-aarch64-gui.exe b/crates/uv-trampoline-builder/trampolines/uv-trampoline-aarch64-gui.exe
index 25009cb3c..0cdcef8a6 100755
Binary files a/crates/uv-trampoline-builder/trampolines/uv-trampoline-aarch64-gui.exe and b/crates/uv-trampoline-builder/trampolines/uv-trampoline-aarch64-gui.exe differ
diff --git a/crates/uv-trampoline-builder/trampolines/uv-trampoline-i686-console.exe b/crates/uv-trampoline-builder/trampolines/uv-trampoline-i686-console.exe
index ea1c867b2..bc46f34f1 100755
Binary files a/crates/uv-trampoline-builder/trampolines/uv-trampoline-i686-console.exe and b/crates/uv-trampoline-builder/trampolines/uv-trampoline-i686-console.exe differ
diff --git a/crates/uv-trampoline-builder/trampolines/uv-trampoline-i686-gui.exe b/crates/uv-trampoline-builder/trampolines/uv-trampoline-i686-gui.exe
index 0811c065c..b95f3cc4b 100755
Binary files a/crates/uv-trampoline-builder/trampolines/uv-trampoline-i686-gui.exe and b/crates/uv-trampoline-builder/trampolines/uv-trampoline-i686-gui.exe differ
diff --git a/crates/uv-trampoline-builder/trampolines/uv-trampoline-x86_64-console.exe b/crates/uv-trampoline-builder/trampolines/uv-trampoline-x86_64-console.exe
index 5cdd48d5b..3e3117c2b 100755
Binary files a/crates/uv-trampoline-builder/trampolines/uv-trampoline-x86_64-console.exe and b/crates/uv-trampoline-builder/trampolines/uv-trampoline-x86_64-console.exe differ
diff --git a/crates/uv-trampoline-builder/trampolines/uv-trampoline-x86_64-gui.exe b/crates/uv-trampoline-builder/trampolines/uv-trampoline-x86_64-gui.exe
index 22b461aee..97e6d5cab 100755
Binary files a/crates/uv-trampoline-builder/trampolines/uv-trampoline-x86_64-gui.exe and b/crates/uv-trampoline-builder/trampolines/uv-trampoline-x86_64-gui.exe differ
diff --git a/crates/uv-trampoline/.cargo/config.toml b/crates/uv-trampoline/.cargo/config.toml
index 992e4ab63..c5fcd3c82 100644
--- a/crates/uv-trampoline/.cargo/config.toml
+++ b/crates/uv-trampoline/.cargo/config.toml
@@ -2,3 +2,8 @@
 build-std = ["std", "panic_abort"]
 build-std-features = ["compiler-builtins-mem"]
 panic-abort-tests = true
+
+# Make PE binaries reproducible: replace timestamps and debug GUIDs with
+# content hashes so identical source produces identical bytes.
+[target.'cfg(windows)']
+rustflags = ["-C", "link-arg=/Brepro"]
diff --git a/crates/uv-trampoline/Dockerfile b/crates/uv-trampoline/Dockerfile
new file mode 100644
index 000000000..09128c626
--- /dev/null
+++ b/crates/uv-trampoline/Dockerfile
@@ -0,0 +1,67 @@
+# Reproducible cross-compilation environment for Windows trampolines.
+#
+# All toolchain versions are pinned for binary reproducibility.
+# This image provides the build environment; the workspace is bind-mounted
+# at runtime by scripts/build-trampolines.sh.
+
+ARG UBUNTU_SNAPSHOT=20260127T200000Z
+
+ARG RUST_NIGHTLY=nightly-2025-11-02
+
+ARG CARGO_XWIN_VERSION=0.21.4
+ARG XWIN_SDK_VERSION=10.0.22621
+ARG XWIN_CRT_VERSION=14.44.17.14
+
+FROM ubuntu:26.04@sha256:4095ef613201918336b5d7d00be15d8b09c72ddb77c80bca249c255887a64d87 AS base
+
+ARG RUST_NIGHTLY
+ARG UBUNTU_SNAPSHOT
+
+ENV HOME=/app
+ENV CARGO_HOME=${HOME}/rust/cargo
+ENV RUSTUP_HOME=${HOME}/rust/rustup
+ENV XWIN_CACHE_DIR=${HOME}/xwin-cache
+
+WORKDIR ${HOME}
+
+# Install build dependencies
+RUN apt install -y --update ca-certificates && \
+    apt install -y --update --snapshot ${UBUNTU_SNAPSHOT} \
+        curl \
+        llvm \
+        clang \
+        lld \
+    && ln -s /usr/bin/llvm-mt /usr/bin/mt.exe \
+    && rm -rf /var/lib/apt/lists/*
+
+# Install Rust nightly toolchain with Windows targets
+RUN curl --proto '=https' --tlsv1.2 -sSf https://sh.rustup.rs | \
+    sh -s -- -y --default-toolchain=${RUST_NIGHTLY} --profile=minimal
+
+ENV PATH="${CARGO_HOME}/bin:${PATH}"
+
+RUN rustup component add rust-src --toolchain ${RUST_NIGHTLY}-x86_64-unknown-linux-gnu && \
+    rustup target add --toolchain ${RUST_NIGHTLY} \
+        i686-pc-windows-msvc \
+        x86_64-pc-windows-msvc \
+        aarch64-pc-windows-msvc
+
+# Install cargo-xwin and prefetch the Windows SDK/CRT
+FROM base AS xwin-cache
+
+ARG CARGO_XWIN_VERSION
+ARG XWIN_SDK_VERSION
+ARG XWIN_CRT_VERSION
+
+RUN cargo install cargo-xwin@${CARGO_XWIN_VERSION}
+
+RUN cargo xwin cache xwin \
+      --xwin-sdk-version ${XWIN_SDK_VERSION} \
+      --xwin-crt-version ${XWIN_CRT_VERSION} \
+      --xwin-arch x86,x86_64,aarch64
+
+FROM base
+
+COPY --chmod=a+rwX --from=xwin-cache ${HOME}/xwin-cache ${HOME}/xwin-cache
+RUN chmod a+w ${HOME}/xwin-cache
+COPY --from=xwin-cache ${CARGO_HOME}/bin/cargo-xwin ${CARGO_HOME}/bin/cargo-xwin
diff --git a/crates/uv-trampoline/README.md b/crates/uv-trampoline/README.md
index 4fec7cc03..a419f504f 100644
--- a/crates/uv-trampoline/README.md
+++ b/crates/uv-trampoline/README.md
@@ -5,6 +5,14 @@ This is a fork of
 
 ## Building
 
+The trampolines checked into the repo use a reproducible dockerfile for auditing.
+
+```shell
+scripts/build-trampolines.sh
+```
+
+The other build options exist for local development.
+
 ### Cross-compiling from Linux
 
 Install [cargo xwin](https://github.com/rust-cross/cargo-xwin). Use your package manager to install
diff --git a/scripts/build-trampolines.sh b/scripts/build-trampolines.sh
new file mode 100755
index 000000000..504dce009
--- /dev/null
+++ b/scripts/build-trampolines.sh
@@ -0,0 +1,49 @@
+#!/bin/bash
+# Build all Windows trampoline executables reproducibly using Docker.
+#
+# Extra arguments are forwarded to the docker build command
+
+set -euo pipefail
+
+SCRIPT_DIR="$(cd "$(dirname "$0")" && pwd)"
+REPO_ROOT="$(cd "$SCRIPT_DIR/.." && pwd)"
+TRAMPOLINE_DIR="$REPO_ROOT/crates/uv-trampoline"
+OUTPUT_DIR="$REPO_ROOT/crates/uv-trampoline-builder/trampolines"
+
+# Read the nightly toolchain from rust-toolchain.toml
+TOOLCHAIN="$(grep '^channel' "$TRAMPOLINE_DIR/rust-toolchain.toml" | sed 's/.*"\(.*\)"/\1/')"
+
+# Build the pinned toolchain image.
+docker buildx build -t uv-trampoline-builder --load \
+    -f "$TRAMPOLINE_DIR/Dockerfile" "$TRAMPOLINE_DIR" \
+    "$@"
+
+# Build trampolines inside the container with the workspace bind-mounted.
+# The working directory must be the trampoline crate so cargo picks up
+# .cargo/config.toml (which enables build-std).
+docker run --rm \
+    -v "$REPO_ROOT:/workspace:ro" \
+    -v "$OUTPUT_DIR:/output" \
+    -w /workspace/crates/uv-trampoline \
+    uv-trampoline-builder \
+    bash -c '
+        set -euo pipefail
+        export CARGO_TARGET_DIR=/tmp/target
+
+        cargo +"'"$TOOLCHAIN"'" xwin build --xwin-arch x86 --release --target i686-pc-windows-msvc
+        cargo +"'"$TOOLCHAIN"'" xwin build --release --target x86_64-pc-windows-msvc
+        cargo +"'"$TOOLCHAIN"'" xwin build --release --target aarch64-pc-windows-msvc
+
+        for arch in i686 x86_64 aarch64; do
+            for variant in console gui; do
+                cp /tmp/target/$arch-pc-windows-msvc/release/uv-trampoline-$variant.exe \
+                    /output/uv-trampoline-$arch-$variant.exe
+            done
+        done
+    '
+
+# Zero out non-deterministic PE fields (timestamps, debug GUIDs) so that
+# builds are byte-for-byte reproducible despite LLVM non-determinism.
+cargo run --quiet -p uv-trampoline-builder --bin normalize-pe-timestamps -- "$OUTPUT_DIR"/*.exe
+
+echo "Done. Trampolines written to $OUTPUT_DIR"