diff --git a/.github/workflows/test-windows.yml b/.github/workflows/test-windows.yml
index d53daec1365..2b15d6aea3c 100644
--- a/.github/workflows/test-windows.yml
+++ b/.github/workflows/test-windows.yml
@@ -68,8 +68,8 @@ jobs:
     - name: Install dependencies
       id: install
       run: |
-        7z x winbuild\depends\nasm-2.14.02-win64.zip "-o$env:RUNNER_WORKSPACE\"
-        echo "$env:RUNNER_WORKSPACE\nasm-2.14.02" >> $env:GITHUB_PATH
+        7z x winbuild\depends\nasm-2.15.05-win64.zip "-o$env:RUNNER_WORKSPACE\"
+        echo "$env:RUNNER_WORKSPACE\nasm-2.15.05" >> $env:GITHUB_PATH
 
         winbuild\depends\gs9533w32.exe /S
         echo "C:\Program Files (x86)\gs\gs9.53.3\bin" >> $env:GITHUB_PATH
diff --git a/setup.py b/setup.py
index 10992779e00..66bab7ecbe6 100755
--- a/setup.py
+++ b/setup.py
@@ -727,9 +727,11 @@ def build_extensions(self):
         if feature.tiff:
             libs.append(feature.tiff)
             defs.append(("HAVE_LIBTIFF", None))
-            # FIXME the following define should be detected automatically
-            #       based on system libtiff, see #4237
-            if PLATFORM_MINGW:
+            if sys.platform == "win32":
+                # This define needs to be defined if-and-only-if it was defined
+                # when compiling LibTIFF. LibTIFF doesn't expose it in `tiffconf.h`,
+                # so we have to guess; by default it is defined in all Windows builds.
+                # See #4237, #5243, #5359 for more information.
                 defs.append(("USE_WIN32_FILEIO", None))
         if feature.xcb:
             libs.append(feature.xcb)
diff --git a/winbuild/build_prepare.py b/winbuild/build_prepare.py
index a20fef02b1e..102dfe1757c 100644
--- a/winbuild/build_prepare.py
+++ b/winbuild/build_prepare.py
@@ -145,9 +145,9 @@ def cmd_msbuild(
         "filename": "tiff-4.2.0.tar.gz",
         "dir": "tiff-4.2.0",
         "build": [
-            cmd_copy(r"{winbuild_dir}\tiff.opt", "nmake.opt"),
-            cmd_nmake("makefile.vc", "clean"),
-            cmd_nmake("makefile.vc", "lib"),
+            cmd_cmake("-DBUILD_SHARED_LIBS:BOOL=OFF"),
+            cmd_nmake(target="clean"),
+            cmd_nmake(target="tiff"),
         ],
         "headers": [r"libtiff\tiff*.h"],
         "libs": [r"libtiff\*.lib"],
diff --git a/winbuild/tiff.opt b/winbuild/tiff.opt
deleted file mode 100644
index d82c51678d6..00000000000
--- a/winbuild/tiff.opt
+++ /dev/null
@@ -1,220 +0,0 @@
-# $Id: nmake.opt,v 1.18 2006/06/07 16:33:45 dron Exp $
-#
-# Copyright (C) 2004, Andrey Kiselev <dron@ak4719.spb.edu>
-#
-# Permission to use, copy, modify, distribute, and sell this software and
-# its documentation for any purpose is hereby granted without fee, provided
-# that (i) the above copyright notices and this permission notice appear in
-# all copies of the software and related documentation, and (ii) the names of
-# Sam Leffler and Silicon Graphics may not be used in any advertising or
-# publicity relating to the software without the specific, prior written
-# permission of Sam Leffler and Silicon Graphics.
-#
-# THE SOFTWARE IS PROVIDED "AS-IS" AND WITHOUT WARRANTY OF ANY KIND,
-# EXPRESS, IMPLIED OR OTHERWISE, INCLUDING WITHOUT LIMITATION, ANY
-# WARRANTY OF MERCHANTABILITY OR FITNESS FOR A PARTICULAR PURPOSE.
-#
-# IN NO EVENT SHALL SAM LEFFLER OR SILICON GRAPHICS BE LIABLE FOR
-# ANY SPECIAL, INCIDENTAL, INDIRECT OR CONSEQUENTIAL DAMAGES OF ANY KIND,
-# OR ANY DAMAGES WHATSOEVER RESULTING FROM LOSS OF USE, DATA OR PROFITS,
-# WHETHER OR NOT ADVISED OF THE POSSIBILITY OF DAMAGE, AND ON ANY THEORY OF
-# LIABILITY, ARISING OUT OF OR IN CONNECTION WITH THE USE OR PERFORMANCE
-# OF THIS SOFTWARE.
-
-# Compile time parameters for MS Visual C++ compiler.
-# You may edit this file to specify building options.
-
-#
-###### Edit the following lines to choose a feature set you need. #######
-#
-
-#
-# Select WINMODE_CONSOLE to build a library which reports errors to stderr, or
-# WINMODE_WINDOWED to build such that errors are reported via MessageBox().
-#
-WINMODE_CONSOLE = 1
-#WINMODE_WINDOWED = 1
-
-#
-# Comment out the following lines to disable internal codecs.
-#
-# Support for CCITT Group 3 & 4 algorithms
-CCITT_SUPPORT	= 1
-# Support for Macintosh PackBits algorithm
-PACKBITS_SUPPORT = 1
-# Support for LZW algorithm
-LZW_SUPPORT	= 1
-# Support for ThunderScan 4-bit RLE algorithm
-THUNDER_SUPPORT	= 1
-# Support for NeXT 2-bit RLE algorithm
-NEXT_SUPPORT	= 1
-# Support for LogLuv high dynamic range encoding
-LOGLUV_SUPPORT	= 1
-
-#
-# Uncomment and edit following lines to enable JPEG support.
-#
-JPEG_SUPPORT	= 1
-JPEG_INCLUDE	= -I$(INCLIB)
-JPEG_LIB 	= $(INCLIB)/libjpeg.lib
-
-#
-# Uncomment and edit following lines to enable ZIP support
-# (required for Deflate compression and Pixar log-format)
-#
-ZIP_SUPPORT	= 1
-ZLIB_INCLUDE	= -I$(INCLIB)
-ZLIB_LIB 	= $(INCLIB)/zlib.lib
-
-# Indicate if the compiler provides strtoll/strtoull (default 1)
-# Users of MSVC++ 14.0 ("Visual Studio 2015") and later should set this to 1
-HAVE_STRTOLL = 1
-
-#
-# Uncomment and edit following lines to enable ISO JBIG support
-#
-#JBIG_SUPPORT	= 1
-#JBIGDIR 	= d:/projects/jbigkit
-#JBIG_INCLUDE	= -I$(JBIGDIR)/libjbig
-#JBIG_LIB 	= $(JBIGDIR)/libjbig/jbig.lib
-
-#
-# Uncomment following line to enable Pixar log-format algorithm
-# (Zlib required).
-#
-#PIXARLOG_SUPPORT = 1
-
-#
-# Comment out the following lines to disable strip chopping
-# (whether or not to convert single-strip uncompressed images to multiple
-# strips of specified size to reduce memory usage). Default strip size
-# is 8192 bytes, it can be configured via the STRIP_SIZE_DEFAULT parameter
-#
-STRIPCHOP_SUPPORT = 1
-STRIP_SIZE_DEFAULT = 8192
-
-#
-# Comment out the following lines to disable treating the fourth sample with
-# no EXTRASAMPLE_ value as being ASSOCALPHA. Many packages produce RGBA
-# files but don't mark the alpha properly.
-#
-EXTRASAMPLE_AS_ALPHA_SUPPORT = 1
-
-#
-# Comment out the following lines to disable picking up YCbCr subsampling
-# info from the JPEG data stream to support files lacking the tag.
-# See Bug 168 in Bugzilla, and JPEGFixupTestSubsampling() for details.
-#
-CHECK_JPEG_YCBCR_SUBSAMPLING = 1
-
-#
-####################### Compiler related options. #######################
-#
-
-#
-# Pick debug or optimized build flags.  We default to an optimized build
-# with no debugging information.
-# NOTE: /EHsc option required if you want to build the C++ stream API
-#
-OPTFLAGS =	/Ox /MD /EHsc /W3 /D_CRT_SECURE_NO_DEPRECATE
-#OPTFLAGS = 	/Zi
-
-#
-# Uncomment following line to enable using Windows Common RunTime Library
-# instead of Windows specific system calls. See notes on top of tif_unix.c
-# module for details.
-#
-USE_WIN_CRT_LIB = 1
-
-# Compiler specific options. You may probably want to adjust compilation
-# parameters in CFLAGS variable. Refer to your compiler documentation
-# for the option reference.
-#
-MAKE	=	nmake /nologo
-CC	=	cl /nologo
-CXX	=	cl /nologo
-AR	=	lib /nologo
-LD	=	link /nologo
-
-CFLAGS  =	$(OPTFLAGS) $(INCL) $(EXTRAFLAGS)
-CXXFLAGS =	$(OPTFLAGS) $(INCL) $(EXTRAFLAGS)
-EXTRAFLAGS =
-LIBS	=
-
-# Name of the output shared library
-DLLNAME	= libtiff.dll
-
-#
-########### There is nothing to edit below this line normally. ###########
-#
-
-# Set the native cpu bit order
-EXTRAFLAGS	= -DFILLODER_LSB2MSB $(EXTRAFLAGS)
-
-!IFDEF WINMODE_WINDOWED
-EXTRAFLAGS	= -DTIF_PLATFORM_WINDOWED $(EXTRAFLAGS)
-LIBS		= user32.lib $(LIBS)
-!ELSE
-EXTRAFLAGS	= -DTIF_PLATFORM_CONSOLE $(EXTRAFLAGS)
-!ENDIF
-
-# Codec stuff
-!IFDEF CCITT_SUPPORT
-EXTRAFLAGS	= -DCCITT_SUPPORT $(EXTRAFLAGS)
-!ENDIF
-
-!IFDEF PACKBITS_SUPPORT
-EXTRAFLAGS	= -DPACKBITS_SUPPORT $(EXTRAFLAGS)
-!ENDIF
-
-!IFDEF LZW_SUPPORT
-EXTRAFLAGS	=  -DLZW_SUPPORT $(EXTRAFLAGS)
-!ENDIF
-
-!IFDEF THUNDER_SUPPORT
-EXTRAFLAGS	= -DTHUNDER_SUPPORT $(EXTRAFLAGS)
-!ENDIF
-
-!IFDEF NEXT_SUPPORT
-EXTRAFLAGS	= -DNEXT_SUPPORT $(EXTRAFLAGS)
-!ENDIF
-
-!IFDEF LOGLUV_SUPPORT
-EXTRAFLAGS	= -DLOGLUV_SUPPORT $(EXTRAFLAGS)
-!ENDIF
-
-!IFDEF JPEG_SUPPORT
-LIBS		= $(LIBS) $(JPEG_LIB)
-EXTRAFLAGS	= -DJPEG_SUPPORT -DOJPEG_SUPPORT $(EXTRAFLAGS)
-!ENDIF
-
-!IFDEF ZIP_SUPPORT
-LIBS		= $(LIBS) $(ZLIB_LIB)
-EXTRAFLAGS	= -DZIP_SUPPORT $(EXTRAFLAGS)
-!IFDEF PIXARLOG_SUPPORT
-EXTRAFLAGS	= -DPIXARLOG_SUPPORT $(EXTRAFLAGS)
-!ENDIF
-!ENDIF
-
-!IFDEF JBIG_SUPPORT
-LIBS		= $(LIBS) $(JBIG_LIB)
-EXTRAFLAGS	= -DJBIG_SUPPORT $(EXTRAFLAGS)
-!ENDIF
-
-!IFDEF STRIPCHOP_SUPPORT
-EXTRAFLAGS	= -DSTRIPCHOP_DEFAULT=TIFF_STRIPCHOP -DSTRIP_SIZE_DEFAULT=$(STRIP_SIZE_DEFAULT) $(EXTRAFLAGS)
-!ENDIF
-
-!IFDEF EXTRASAMPLE_AS_ALPHA_SUPPORT
-EXTRAFLAGS	= -DDEFAULT_EXTRASAMPLE_AS_ALPHA $(EXTRAFLAGS)
-!ENDIF
-
-!IFDEF CHECK_JPEG_YCBCR_SUBSAMPLING
-EXTRAFLAGS	= -DCHECK_JPEG_YCBCR_SUBSAMPLING $(EXTRAFLAGS)
-!ENDIF
-
-!IFDEF USE_WIN_CRT_LIB
-EXTRAFLAGS	= -DAVOID_WIN32_FILEIO $(EXTRAFLAGS)
-!ELSE
-EXTRAFLAGS	= -DUSE_WIN32_FILEIO $(EXTRAFLAGS)
-!ENDIF