diff --git a/changes/4164.feature.md b/changes/4164.feature.md
new file mode 100644
index 0000000000..61b9280468
--- /dev/null
+++ b/changes/4164.feature.md
@@ -0,0 +1 @@
+The Table widget on WinForms can now display icons in all columns. Previously, icons were only supported in the first column.
diff --git a/docs/en/reference/api/widgets/table.md b/docs/en/reference/api/widgets/table.md
index 618920e03b..38c9027c10 100644
--- a/docs/en/reference/api/widgets/table.md
+++ b/docs/en/reference/api/widgets/table.md
@@ -74,8 +74,7 @@ The set of known accessors and their order for creating rows from lists and tupl
 
 - Widgets in cells is a beta API which may change in future, and is currently only supported on macOS.
 - macOS does not support changing the font used to render table content.
-- On Winforms, icons are only supported in the first column. On Android, icons are not supported at all.
-- The Android implementation is [not scalable](https://github.com/beeware/toga/issues/1392) beyond about 1,000 cells.
+- Icons in tables are not supported on Android, and the implementation is [not scalable](https://github.com/beeware/toga/issues/1392) beyond about 1,000 cells.
 
 ## Reference
 
diff --git a/winforms/src/toga_winforms/libs/comctl32.py b/winforms/src/toga_winforms/libs/comctl32.py
new file mode 100644
index 0000000000..d41db24e1e
--- /dev/null
+++ b/winforms/src/toga_winforms/libs/comctl32.py
@@ -0,0 +1,25 @@
+from ctypes import windll
+from ctypes.wintypes import BOOL, HWND, LPARAM, UINT, WPARAM
+
+from .comctl32classes import SUBCLASSPROC
+from .win32 import DWORD_PTR, LRESULT, UINT_PTR
+
+comctl32 = windll.comctl32
+
+
+# https://learn.microsoft.com/en-us/windows/win32/api/commctrl/nf-commctrl-defsubclassproc
+DefSubclassProc = comctl32.DefSubclassProc
+DefSubclassProc.restype = LRESULT
+DefSubclassProc.argtypes = [HWND, UINT, WPARAM, LPARAM]
+
+
+# https://learn.microsoft.com/en-us/windows/win32/api/commctrl/nf-commctrl-setwindowsubclass
+RemoveWindowSubclass = comctl32.RemoveWindowSubclass
+RemoveWindowSubclass.restype = BOOL
+RemoveWindowSubclass.argtypes = [HWND, SUBCLASSPROC, UINT_PTR]
+
+
+# https://learn.microsoft.com/en-us/windows/win32/api/commctrl/nf-commctrl-setwindowsubclass
+SetWindowSubclass = comctl32.SetWindowSubclass
+SetWindowSubclass.restype = BOOL
+SetWindowSubclass.argtypes = [HWND, SUBCLASSPROC, UINT_PTR, DWORD_PTR]
diff --git a/winforms/src/toga_winforms/libs/comctl32classes.py b/winforms/src/toga_winforms/libs/comctl32classes.py
new file mode 100644
index 0000000000..95a279eaf9
--- /dev/null
+++ b/winforms/src/toga_winforms/libs/comctl32classes.py
@@ -0,0 +1,59 @@
+from ctypes import (
+    WINFUNCTYPE,
+    Structure as c_Structure,
+)
+from ctypes.wintypes import HWND, INT, LPARAM, LPWSTR, UINT, WPARAM
+
+from .win32 import DWORD_PTR, INT_PTR, LRESULT, PUINT, UINT_PTR
+
+
+# https://learn.microsoft.com/en-us/windows/win32/api/commctrl/ns-commctrl-lvitemw
+class LVITEMW(c_Structure):
+    _fields_ = [
+        ("uiMask", UINT),
+        ("iItem", INT),
+        ("iSubItem", INT),
+        ("state", UINT),
+        ("stateMask", UINT),
+        ("pszText", LPWSTR),
+        ("cchTextMax", INT),
+        ("iImage", INT),
+        ("lParam", LPARAM),
+        ("iIndent", INT),
+        ("iGroupId", INT),
+        ("cColumns", UINT),
+        ("puColumns", PUINT),
+        ("piColFmt", INT_PTR),
+        ("iGroup", INT),
+    ]
+
+
+# https://learn.microsoft.com/en-us/windows/win32/api/winuser/ns-winuser-nmhdr
+class NMHDR(c_Structure):
+    _fields_ = [
+        ("hwndFrom", HWND),
+        ("idFrom", UINT_PTR),
+        ("code", UINT),
+    ]
+
+
+# https://learn.microsoft.com/en-us/windows/win32/api/commctrl/ns-commctrl-nmlvdispinfow
+class NMLVDISPINFOW(c_Structure):
+    _fields_ = [
+        ("hdr", NMHDR),
+        ("item", LVITEMW),
+    ]
+
+
+# https://learn.microsoft.com/en-us/windows/win32/api/commctrl/nc-commctrl-subclassproc
+SUBCLASSPROC = WINFUNCTYPE(
+    # Return type:
+    LRESULT,
+    # Argument types:
+    HWND,
+    UINT,
+    WPARAM,
+    LPARAM,
+    UINT_PTR,
+    DWORD_PTR,
+)
diff --git a/winforms/src/toga_winforms/libs/user32.py b/winforms/src/toga_winforms/libs/user32.py
index 32d2698df2..693e163510 100644
--- a/winforms/src/toga_winforms/libs/user32.py
+++ b/winforms/src/toga_winforms/libs/user32.py
@@ -1,7 +1,10 @@
-from ctypes import c_void_p, windll, wintypes
+from ctypes import c_void_p, windll
+from ctypes.wintypes import BOOL, DWORD, HMONITOR, HWND, LPARAM, LPRECT, UINT, WPARAM
 
 from System import Environment
 
+from .win32 import LRESULT
+
 user32 = windll.user32
 
 
@@ -13,7 +16,7 @@
 win_version = Environment.OSVersion.Version
 if (win_version.Major, win_version.Minor, win_version.Build) >= (10, 0, 15063):
     SetProcessDpiAwarenessContext = user32.SetProcessDpiAwarenessContext
-    SetProcessDpiAwarenessContext.restype = wintypes.BOOL
+    SetProcessDpiAwarenessContext.restype = BOOL
     SetProcessDpiAwarenessContext.argtypes = [c_void_p]
 
     SetThreadDpiAwarenessContext = user32.SetThreadDpiAwarenessContext
@@ -32,5 +35,11 @@
 MONITOR_DEFAULTTONEAREST = 2
 
 MonitorFromRect = user32.MonitorFromRect
-MonitorFromRect.restype = wintypes.HMONITOR
-MonitorFromRect.argtypes = [wintypes.LPRECT, wintypes.DWORD]
+MonitorFromRect.restype = HMONITOR
+MonitorFromRect.argtypes = [LPRECT, DWORD]
+
+
+# https://learn.microsoft.com/en-us/windows/win32/api/winuser/nf-winuser-sendmessagew
+SendMessageW = user32.SendMessageW
+SendMessageW.restype = LRESULT
+SendMessageW.argtypes = [HWND, UINT, WPARAM, LPARAM]
diff --git a/winforms/src/toga_winforms/libs/win32.py b/winforms/src/toga_winforms/libs/win32.py
new file mode 100644
index 0000000000..59ab01c7ac
--- /dev/null
+++ b/winforms/src/toga_winforms/libs/win32.py
@@ -0,0 +1,8 @@
+from ctypes import c_size_t
+from ctypes.wintypes import LPARAM
+
+LRESULT = LPARAM  # LPARAM is essentially equivalent to LRESULT
+UINT_PTR = c_size_t
+DWORD_PTR = c_size_t
+PUINT = c_size_t
+INT_PTR = c_size_t
diff --git a/winforms/src/toga_winforms/libs/windowconstants.py b/winforms/src/toga_winforms/libs/windowconstants.py
new file mode 100644
index 0000000000..d15a6ba50b
--- /dev/null
+++ b/winforms/src/toga_winforms/libs/windowconstants.py
@@ -0,0 +1,23 @@
+# Window constants
+
+# Edit Messages
+EM_SETCUEBANNER = 0x1501
+
+# List-View Item Format
+LVIF_TEXT = 0x0001
+LVIF_IMAGE = 0x0002
+LVIF_STATE = 0x0008
+
+# List-View Management
+LVM_GETEXTENDEDLISTVIEWSTYLE = 0x1037
+LVM_SETEXTENDEDLISTVIEWSTYLE = 0x1036
+
+# List-View Notification
+LVN_GETDISPINFOW = 0xFFFFFF4F
+
+# List-View Styles (Extended)
+LVS_EX_SUBITEMIMAGES = 0x2
+
+# Window Message
+WM_NCDESTROY = 0x0082
+WM_REFLECT_NOTIFY = 0x204E
diff --git a/winforms/src/toga_winforms/widgets/multilinetextinput.py b/winforms/src/toga_winforms/widgets/multilinetextinput.py
index 7ac7fa8dd2..06e4b39a6d 100644
--- a/winforms/src/toga_winforms/widgets/multilinetextinput.py
+++ b/winforms/src/toga_winforms/widgets/multilinetextinput.py
@@ -44,6 +44,9 @@ def winforms_lost_focus(self, sender, event):
         if self.native.Text == "":
             self._set_placeholder_visible(True)
 
+    def get_placeholder(self):
+        return self._placeholder
+
     def set_placeholder(self, value):
         self._placeholder = value
         if self._placeholder_visible:
diff --git a/winforms/src/toga_winforms/widgets/table.py b/winforms/src/toga_winforms/widgets/table.py
index 468e612ac8..fbcbaed8f3 100644
--- a/winforms/src/toga_winforms/widgets/table.py
+++ b/winforms/src/toga_winforms/widgets/table.py
@@ -1,9 +1,16 @@
+from ctypes import POINTER, cast
+from ctypes.wintypes import HWND, LPARAM, UINT, WPARAM
 from warnings import warn
 
 import System.Windows.Forms as WinForms
 
 from toga.handlers import WeakrefCallable
 
+from ..libs import windowconstants as wc
+from ..libs.comctl32 import DefSubclassProc, RemoveWindowSubclass, SetWindowSubclass
+from ..libs.comctl32classes import LVITEMW, NMHDR, NMLVDISPINFOW, SUBCLASSPROC
+from ..libs.user32 import SendMessageW
+from ..libs.win32 import LRESULT
 from .base import Widget
 
 
@@ -25,9 +32,24 @@ def _multiple_select(self):
     def _data(self):
         return self.interface.data
 
+    def __del__(self):
+        # The object self.pfn_subclass is a python class and is part of the native
+        # Windows process. When a Table is removed by the python GC, self.pfn_subclass
+        # is also removed and the Windows process has a dangling pointer. Calling
+        # Dispose() here fixes the problem by removing the self.pfn_subclass from the
+        # Windows process.
+        self.native.Dispose()
+
     def create(self):
+        self.pfn_subclass = SUBCLASSPROC(self._subclass_proc)
         self.native = WinForms.ListView()
+        self._set_subclass()
+
+        self.native.HandleCreated += WeakrefCallable(self.handle_created)
+        self.native.HandleDestroyed += WeakrefCallable(self.handle_destroyed)
+
         self.native.View = WinForms.View.Details
+        self._enable_multi_icon_style()
         self._cache = []
         self._first_item = 0
         self._pending_resize = True
@@ -67,6 +89,68 @@ def create(self):
         )
         self.add_action_events()
 
+    def _enable_multi_icon_style(self):
+        list_view_handle = int(self.native.Handle.ToString())
+
+        # Use SendMessage over PostMessage since the ListView object is on the same
+        # thread as the messaging call.
+        old_style = SendMessageW(
+            list_view_handle, wc.LVM_GETEXTENDEDLISTVIEWSTYLE, 0, 0
+        )
+        new_style = old_style | wc.LVS_EX_SUBITEMIMAGES
+
+        SendMessageW(list_view_handle, wc.LVM_SETEXTENDEDLISTVIEWSTYLE, 0, new_style)
+
+    def handle_created(self, sender, e):
+        self._set_subclass()
+
+    def handle_destroyed(self, sender, e):
+        # Remove the subclass when a handle is destroyed to prevent a memory leak.
+        self._remove_subclass()
+
+    def _set_subclass(self):
+        SetWindowSubclass(int(self.native.Handle.ToString()), self.pfn_subclass, 0, 0)
+
+    def _remove_subclass(self):
+        RemoveWindowSubclass(int(self.native.Handle.ToString()), self.pfn_subclass, 0)
+
+    def _subclass_proc(
+        self,
+        hWnd: int,
+        uMsg: int,
+        wParam: int,
+        lParam: int,
+        uIdSubclass: int,
+        dwRefData: int,
+    ) -> LRESULT:
+        # Remove the window subclass in the way recommended by Raymond Chen here:
+        # https://devblogs.microsoft.com/oldnewthing/20031111-00/?p=41883
+        if uMsg == wc.WM_NCDESTROY:
+            RemoveWindowSubclass(hWnd, self.pfn_subclass, uIdSubclass)
+
+        if uMsg == wc.WM_REFLECT_NOTIFY:
+            phdr = cast(lParam, POINTER(NMHDR)).contents
+            code = phdr.code
+            if code == wc.LVN_GETDISPINFOW:
+                disp_info = cast(lParam, POINTER(NMLVDISPINFOW)).contents
+                self._set_subitem_icon(disp_info.item)
+
+        # Call the original window procedure
+        return DefSubclassProc(HWND(hWnd), UINT(uMsg), WPARAM(wParam), LPARAM(lParam))
+
+    def _set_subitem_icon(self, lvitem: LVITEMW):
+        row_index = lvitem.iItem
+        column_index = lvitem.iSubItem
+
+        _, icon_indices = self._toga_retrieve_virtual_item(row_index)
+
+        # Add the icon property if it doesn't exist.
+        if lvitem.uiMask == (wc.LVIF_TEXT | wc.LVIF_STATE):
+            lvitem.uiMask = wc.LVIF_TEXT | wc.LVIF_STATE | wc.LVIF_IMAGE
+
+        if lvitem.uiMask & wc.LVIF_IMAGE != 0 and icon_indices[column_index] > -1:
+            lvitem.iImage = icon_indices[column_index]
+
     def add_action_events(self):
         self.native.MouseDoubleClick += WeakrefCallable(self.winforms_double_click)
 
@@ -80,14 +164,17 @@ def winforms_retrieve_virtual_item(self, sender, e):
         # Because ListView is in VirtualMode, it's necessary implement
         # VirtualItemsSelectionRangeChanged event to create ListViewItem
         # when it's needed
+        e.Item, _ = self._toga_retrieve_virtual_item(e.ItemIndex)
+
+    def _toga_retrieve_virtual_item(self, item_index):
         if (
             self._cache
-            and e.ItemIndex >= self._first_item
-            and e.ItemIndex < self._first_item + len(self._cache)
+            and item_index >= self._first_item
+            and item_index < self._first_item + len(self._cache)
         ):
-            e.Item = self._cache[e.ItemIndex - self._first_item]
+            return self._cache[item_index - self._first_item]
         else:
-            e.Item = self._new_item(e.ItemIndex)
+            return self._new_item(item_index)
 
     def winforms_cache_virtual_items(self, sender, e):
         if (
@@ -194,28 +281,26 @@ def _resize_columns(self):
     def change_source(self, source):
         self.update_data()
 
+    def _icon_index(self, row, column) -> int:
+        icon = column.icon(row)
+        return -1 if icon is None else self._image_index(icon._impl)
+
     def _new_item(self, index):
-        item = self._data[index]
+        row = self._data[index]
 
         missing_value = self.interface.missing_value
         lvi = WinForms.ListViewItem(
-            [column.text(item, missing_value) for column in self._columns],
+            [column.text(row, missing_value) for column in self._columns],
         )
-        if any(column.widget(item) is not None for column in self._columns):
+        if any(column.widget(row) is not None for column in self._columns):
             warn(
                 "Winforms does not support the use of widgets in cells",
                 stacklevel=1,
             )
 
-        # If the table has accessors, populate the icons for the table.
-        if self._columns:
-            # TODO: ListView only has built-in support for one icon per row. One
-            # possible workaround is in https://stackoverflow.com/a/46128593.
-            icon = self._columns[0].icon(item)
-            if icon is not None:
-                lvi.ImageIndex = self._image_index(icon._impl)
+        icon_indices = tuple(self._icon_index(row, column) for column in self._columns)
 
-        return lvi
+        return (lvi, icon_indices)
 
     def _image_index(self, icon):
         images = self.native.SmallImageList.Images
diff --git a/winforms/src/toga_winforms/widgets/textinput.py b/winforms/src/toga_winforms/widgets/textinput.py
index 67b88c7896..291b76d133 100644
--- a/winforms/src/toga_winforms/widgets/textinput.py
+++ b/winforms/src/toga_winforms/widgets/textinput.py
@@ -1,5 +1,5 @@
-from ctypes import c_uint, windll
-from ctypes.wintypes import HWND, WPARAM
+from ctypes import c_void_p, c_wchar_p, cast
+from ctypes.wintypes import WPARAM
 from decimal import ROUND_UP
 
 import System.Windows.Forms as WinForms
@@ -8,6 +8,8 @@
 from toga_winforms.colors import native_color
 from toga_winforms.libs.fonts import HorizontalTextAlignment
 
+from ..libs.user32 import SendMessageW
+from ..libs.windowconstants import EM_SETCUEBANNER
 from .base import Widget
 
 
@@ -20,7 +22,7 @@ def create(self):
         self.native.GotFocus += WeakrefCallable(self.winforms_got_focus)
         self.native.LostFocus += WeakrefCallable(self.winforms_lost_focus)
 
-        self._placeholder = ""
+        self._placeholder = c_wchar_p("")
 
         self.error_provider = WinForms.ErrorProvider()
         self.error_provider.SetIconAlignment(
@@ -36,21 +38,21 @@ def set_readonly(self, value):
         self.native.ReadOnly = value
 
     def get_placeholder(self):
-        return self._placeholder
+        return self._placeholder.value
 
-    def set_placeholder(self, value):
-        self._placeholder = value
+    def set_placeholder(self, value: str):
+        self._placeholder = c_wchar_p(value)
         # This solution is based on https://stackoverflow.com/questions/4902565.
-        EM_SETCUEBANNER = c_uint(0x1501)
         # value 0 means placeholder is hidden as soon the input gets focus
         # value 1 means placeholder is hidden only after something is typed into input
         show_placeholder_on_focus = WPARAM(1)
-        window_handle = HWND(self.native.Handle.ToInt32())
-        windll.user32.SendMessageW(
+        window_handle = int(self.native.Handle.ToString())
+        placeholder_address = cast(self._placeholder, c_void_p).value
+        SendMessageW(
             window_handle,
             EM_SETCUEBANNER,
             show_placeholder_on_focus,
-            self._placeholder,
+            placeholder_address,
         )
 
     def get_value(self):
diff --git a/winforms/tests_backend/widgets/table.py b/winforms/tests_backend/widgets/table.py
index 98d4246afc..5e05cdfcb7 100644
--- a/winforms/tests_backend/widgets/table.py
+++ b/winforms/tests_backend/widgets/table.py
@@ -30,25 +30,26 @@ def assert_cell_content(self, row, col, value=None, icon=None, widget=None):
             pytest.skip("This backend doesn't support widgets in Tables")
         else:
             lvi = self.native.Items[row]
+
+            _, icon_indices = self.impl._toga_retrieve_virtual_item(row)
+            icon_index = icon_indices[col]
+
             assert lvi.SubItems[col].Text == value
-            if col == 0:
-                if icon is None:
-                    assert lvi.ImageIndex == -1
-                    assert lvi.ImageKey == ""
-                else:
-                    imagelist = self.native.SmallImageList
-                    size = imagelist.ImageSize
-                    assert size.Width == size.Height == 16
-
-                    # The image is resized and copied, so we need to compare the actual
-                    # pixels.
-                    actual = imagelist.Images[lvi.ImageIndex]
-                    expected = Bitmap(icon._impl.bitmap, size)
-                    for x in range(size.Width):
-                        for y in range(size.Height):
-                            assert actual.GetPixel(x, y) == expected.GetPixel(x, y)
-            else:
-                assert icon is None
+            assert lvi.ImageIndex == -1
+            assert lvi.ImageKey == ""
+
+            if icon is not None:
+                imagelist = self.native.SmallImageList
+                size = imagelist.ImageSize
+                assert size.Width == size.Height == 16
+
+                # The image is resized and copied, so we need to compare the actual
+                # pixels.
+                actual = imagelist.Images[icon_index]
+                expected = Bitmap(icon._impl.bitmap, size)
+                for x in range(size.Width):
+                    for y in range(size.Height):
+                        assert actual.GetPixel(x, y) == expected.GetPixel(x, y)
 
     @property
     def max_scroll_position(self):
diff --git a/winforms/tests_backend/widgets/textinput.py b/winforms/tests_backend/widgets/textinput.py
index 770104eee6..81280a63bc 100644
--- a/winforms/tests_backend/widgets/textinput.py
+++ b/winforms/tests_backend/widgets/textinput.py
@@ -24,10 +24,11 @@ def value_hidden(self):
     @property
     def _placeholder(self):
         buffer = ctypes.create_unicode_buffer(1024)
+        buffer_address = ctypes.cast(buffer, ctypes.c_void_p).value
         result = ctypes.windll.user32.SendMessageW(
             HWND(self.native.Handle.ToInt32()),
             c_uint(0x1502),  # EM_GETCUEBANNER
-            buffer,
+            buffer_address,
             LPARAM(ctypes.sizeof(buffer)),
         )
         if not result: