diff --git a/invoke/runners.py b/invoke/runners.py
index f1c888f44..2e10080fb 100644
--- a/invoke/runners.py
+++ b/invoke/runners.py
@@ -51,6 +51,7 @@
     ready_for_reading,
     bytes_to_read,
 )
+from .shims import get_short_path_name
 from .util import has_fileno, isatty, ExceptionHandlingThread
 
 if TYPE_CHECKING:
@@ -415,6 +416,7 @@ def _setup(self, command: str, kwargs: Any) -> None:
         # Echo running command (wants to be early to be included in dry-run)
         if self.opts["echo"]:
             self.echo(command)
+        self.opts["shell"] = get_short_path_name(self.opts["shell"])
         # Prepare common result args.
         # TODO: I hate this. Needs a deeper separate think about tweaking
         # Runner.generate_result in a way that isn't literally just this same
diff --git a/invoke/shims.py b/invoke/shims.py
new file mode 100644
index 000000000..490f0342a
--- /dev/null
+++ b/invoke/shims.py
@@ -0,0 +1,54 @@
+import sys
+
+
+if sys.platform == "win32":
+    from ctypes import (
+        windll,
+        wintypes,
+        create_unicode_buffer,
+    )
+
+    def _get_short_path_name(long_path: str) -> str:
+        # Access `GetShortPathNameW()` function from `kernel32.dll`.
+        GetShortPathNameW = windll.kernel32.GetShortPathNameW
+        GetShortPathNameW.argtypes = [
+            wintypes.LPCWSTR,
+            wintypes.LPWSTR,
+            wintypes.DWORD,
+        ]
+        GetShortPathNameW.restype = wintypes.DWORD
+        # Call function to get short path form.
+        buffer_size = 0
+        while True:
+            buffer_array = create_unicode_buffer(buffer_size)
+            required_size = GetShortPathNameW(
+                long_path,
+                buffer_array,
+                buffer_size,
+            )
+            if required_size > buffer_size:
+                buffer_size = required_size
+            else:
+                return buffer_array.value
+
+else:
+
+    def _get_short_path_name(long_path: str) -> str:
+        return long_path
+
+
+def get_short_path_name(long_path: str) -> str:
+    """
+    Get short path form for long path.
+
+    Only applies to Windows-based systems; on Unix this is a pass-thru.
+
+    .. note::
+        This API converts path strings to the 8.3 format used by earlier
+        tools on the Windows platform.  This format has no spaces.
+
+    :param long_path: Long path such as `shutil.which()` results.
+
+    :returns: `str` Short path form of the long path.
+    """
+    return _get_short_path_name(long_path)
diff --git a/tests/runners.py b/tests/runners.py
index 94c63d8b3..91dc47993 100644
--- a/tests/runners.py
+++ b/tests/runners.py
@@ -231,6 +231,14 @@ def may_be_configured(self):
             runner = self._runner(run={"shell": "/bin/tcsh"})
             assert runner.run(_).shell == "/bin/tcsh"
 
+        def may_be_configured_with_short_path_on_windows(self):
+            skip()
+
+        @skip_if_windows
+        def may_be_configured_with_passthru_on_posix(self):
+            runner = self._runner(run={"shell": "/foo/bar/baz  /bang"})
+            assert runner.run(_).shell == "/foo/bar/baz  /bang"
+
         def kwarg_beats_config(self):
             runner = self._runner(run={"shell": "/bin/tcsh"})
             assert runner.run(_, shell="/bin/zsh").shell == "/bin/zsh"
diff --git a/tests/terminals.py b/tests/terminals.py
index 96d095886..d1cb9cece 100644
--- a/tests/terminals.py
+++ b/tests/terminals.py
@@ -4,7 +4,12 @@
 from unittest.mock import Mock, patch
 from pytest import skip, mark
 
-from invoke.terminals import pty_size, bytes_to_read, WINDOWS
+from invoke.shims import get_short_path_name
+from invoke.terminals import (
+    WINDOWS,
+    bytes_to_read,
+    pty_size,
+)
 
 # Skip on Windows CI, it may blow up on one of these tests
 pytestmark = mark.skipif(
@@ -76,3 +81,11 @@ def returns_FIONREAD_result_when_stream_is_a_tty(self):
 
         def returns_1_on_windows(self):
             skip()
+
+    class get_short_path_name_:
+        def returns_passthru_on_posix(self):
+            short_path = "/foo/bar/baz"
+            assert get_short_path_name(short_path) == short_path
+
+        def returns_shortpath_on_windows(self):
+            skip()