diff --git a/docs/how-tos/index.rst b/docs/how-tos/index.rst
index a73e8439..f2cc2396 100644
--- a/docs/how-tos/index.rst
+++ b/docs/how-tos/index.rst
@@ -47,6 +47,7 @@ Customize builds with overrides, variants, and version handling.
 
    pyproject-overrides
    multiple-versions
+   multiple-version-bootstrap
    pre-release-versions
    release-age-cooldown
 
diff --git a/docs/how-tos/multiple-version-bootstrap.rst b/docs/how-tos/multiple-version-bootstrap.rst
new file mode 100644
index 00000000..4ea1bbeb
--- /dev/null
+++ b/docs/how-tos/multiple-version-bootstrap.rst
@@ -0,0 +1,155 @@
+Multiple Version Bootstrap
+==========================
+
+.. versionadded:: 0.83.0
+
+By default, fromager resolves each package to its single highest matching
+version. The ``--multiple-versions`` flag changes this behavior so that
+fromager resolves and builds **all versions** that match each requirement
+specifier, rather than only the highest one.
+
+This is different from ``--skip-constraints``, which lets you build a
+specific set of conflicting pinned versions.  ``--multiple-versions``
+discovers and builds every matching version automatically.  See
+:doc:`multiple-versions` for the ``--skip-constraints`` option.
+
+When to Use This
+----------------
+
+Use ``--multiple-versions`` when you need to:
+
+- Populate a private package index with every available version of a package
+- Build a broad wheel collection that serves consumers pinned to different
+  versions
+- Test that multiple versions of a package all build from source in your
+  environment
+
+.. note::
+
+   The resulting wheel collection is **not** meant to be installed as a single
+   coherent set. Each version is built independently.
+
+How to Enable It
+----------------
+
+Pass ``--multiple-versions`` to either ``bootstrap`` or
+``bootstrap-parallel``:
+
+.. code-block:: bash
+
+   # Serial bootstrap
+   fromager bootstrap --multiple-versions 'requests>=2.28'
+
+   # Parallel bootstrap
+   fromager bootstrap-parallel --multiple-versions 'requests>=2.28'
+
+This resolves every version of ``requests`` that satisfies ``>=2.28`` and
+bootstraps each one.
+
+You can also use a requirements file:
+
+.. code-block:: bash
+
+   fromager bootstrap --multiple-versions -r requirements.txt
+
+How It Works
+------------
+
+1. **Resolution** --- For each requirement, fromager queries the package index
+   and collects all versions matching the specifier. Without the flag, only the
+   highest version is returned.
+
+2. **Graph population** --- Every resolved version is added to the dependency
+   graph. The highest version is processed first.
+
+3. **Build** --- Each version is bootstrapped independently: its source is
+   downloaded, its dependencies are resolved, and a wheel is built.
+
+4. **Error handling** --- If a particular version fails to build, fromager logs
+   a warning, removes that version from the dependency graph, and continues
+   with the remaining versions. A summary of failed versions is printed at the
+   end.
+
+5. **Constraints disabled** --- ``constraints.txt`` generation is
+   **automatically skipped** because a constraints file cannot represent
+   multiple versions of the same package. You do not need to pass
+   ``--skip-constraints`` separately.
+
+Output Files
+~~~~~~~~~~~~
+
+When ``--multiple-versions`` is active:
+
+- ``build-order.json`` --- created normally, listing every version built
+- ``graph.json`` --- created normally, containing all versions in the
+  dependency graph
+- ``constraints.txt`` --- **not generated**
+
+Combining with Other Flags
+--------------------------
+
+``--test-mode``
+  Supported with serial ``bootstrap`` only. Failures are collected and
+  reported at the end rather than aborting early (same behavior as without
+  ``--multiple-versions``).
+
+``--skip-constraints``
+  Redundant when ``--multiple-versions`` is set. Fromager automatically
+  disables constraint generation. Passing both flags explicitly is
+  harmless --- no duplicate log messages are emitted.
+
+``--max-release-age``
+  Works together with ``--multiple-versions``. Only versions published
+  within the specified number of days are considered.
+
+``bootstrap-parallel``
+  The flag is passed through to the serial bootstrap phase (sdist-only),
+  then the parallel build phase builds the remaining wheels.
+  ``--test-mode`` is not available in parallel builds.
+
+Complete Example
+----------------
+
+Suppose you want to build every ``requests`` release from 2.28 onward.
+
+**1. Create a requirements file**
+
+.. code-block:: text
+
+   requests>=2.28
+
+**2. Run the bootstrap**
+
+.. code-block:: bash
+
+   fromager bootstrap --multiple-versions \
+     --sdists-repo ./sdists-repo \
+     --wheels-repo ./wheels-repo \
+     --work-dir ./work-dir \
+     -r requirements.txt
+
+**3. Verify the built wheels**
+
+.. code-block:: bash
+
+   find wheels-repo/downloads/ -name "requests-*.whl" | sort
+   # requests-2.28.0-py3-none-any.whl
+   # requests-2.28.1-py3-none-any.whl
+   # requests-2.28.2-py3-none-any.whl
+   # ...
+
+If any version failed to build, the log output will include lines like:
+
+.. code-block:: text
+
+   WARNING requests: 1 version(s) failed to bootstrap
+   WARNING   - requests==2.28.0: BuildError: ...
+
+See Also
+--------
+
+- :doc:`multiple-versions` --- building specific conflicting versions
+  with ``--skip-constraints``
+- :doc:`graph-commands/understanding-multiple-versions` --- analyzing
+  multiple versions in dependency graphs
+- :doc:`bootstrap-constraints` --- using constraints for reproducible builds