diff --git a/packages/conf-gtksourceview3/conf-gtksourceview3.0+2/opam b/packages/conf-gtksourceview3/conf-gtksourceview3.0+2/opam
index a4184f3b561..f097c9d0034 100644
--- a/packages/conf-gtksourceview3/conf-gtksourceview3.0+2/opam
+++ b/packages/conf-gtksourceview3/conf-gtksourceview3.0+2/opam
@@ -5,9 +5,9 @@ bug-reports: "https://github.com/ocaml/opam-repository/issues"
 homepage: "https://projects.gnome.org/gtksourceview/"
 license: "LGPL-2.1-or-later"
 build: [
-  ["pkgconf" "--personality=i686-w64-mingw32" "--short-errors" "--print-errors" "gtksourceview-3.0"] {os = "win32" & os-distribution = "cygwin" & host-arch-x86_32:installed}
-  ["pkgconf" "--personality=x86_64-w64-mingw32" "--short-errors" "--print-errors" "gtksourceview-3.0"] {os = "win32" & os-distribution = "cygwin" & host-arch-x86_64:installed}
-  ["pkg-config" "--short-errors" "--print-errors" "gtksourceview-3.0"] {os != "win32" | os-distribution != "cygwin"}
+  ["pkgconf" "--personality=i686-w64-mingw32" "--short-errors" "--print-errors" "gtksourceview-3.0"] {os = "win32" & os-distribution != "cygwinports" & host-arch-x86_32:installed}
+  ["pkgconf" "--personality=x86_64-w64-mingw32" "--short-errors" "--print-errors" "gtksourceview-3.0"] {os = "win32" & os-distribution != "cygwinports" & host-arch-x86_64:installed}
+  ["pkg-config" "--short-errors" "--print-errors" "gtksourceview-3.0"] {os != "win32" | os-distribution = "cygwinports"}
 ]
 depends: [
   "conf-pkg-config" {build}
diff --git a/packages/conf-libevent/conf-libevent.1/opam b/packages/conf-libevent/conf-libevent.1/opam
index e8476b74dc6..e6695c29add 100644
--- a/packages/conf-libevent/conf-libevent.1/opam
+++ b/packages/conf-libevent/conf-libevent.1/opam
@@ -12,7 +12,7 @@ build: [
   "--personality=x86_64-w64-mingw32"
     {os = "win32" & os-distribution != "cygwinports" &
      host-arch-x86_64:installed}
-  "pkg-config" {os != "Win32" | os-distribution != "cygwin"}
+  "pkg-config" {os != "Win32" | os-distribution = "cygwinports"}
   "libevent"
 ]
 depends: [
diff --git a/packages/conf-libffi/conf-libffi.2.0.0/opam b/packages/conf-libffi/conf-libffi.2.0.0/opam
index e152b6ab1f2..737c2772461 100644
--- a/packages/conf-libffi/conf-libffi.2.0.0/opam
+++ b/packages/conf-libffi/conf-libffi.2.0.0/opam
@@ -4,10 +4,10 @@ authors: ["Anthony Green"]
 homepage: "http://sourceware.org/libffi/"
 license: "MIT"
 build: [
-  "pkgconf" {os = "win32" & os-distribution = "cygwin"}
-   "--personality=i686-w64-mingw32" {os = "win32" & os-distribution = "cygwin" & host-arch-x86_32:installed}
-   "--personality=x86_64-w64-mingw32" {os = "win32" & os-distribution = "cygwin" & host-arch-x86_64:installed}
-   "pkg-config" {os != "win32" | os-distribution != "cygwin"}
+  "pkgconf" {os = "win32" & os-distribution != "cygwinports"}
+   "--personality=i686-w64-mingw32" {os = "win32" & os-distribution != "cygwinports" & host-arch-x86_32:installed}
+   "--personality=x86_64-w64-mingw32" {os = "win32" & os-distribution != "cygwinports" & host-arch-x86_64:installed}
+   "pkg-config" {os != "win32" | os-distribution = "cygwinports"}
    "libffi"
 ]
 depexts: [
diff --git a/packages/conf-liblz4/conf-liblz4.1/opam b/packages/conf-liblz4/conf-liblz4.1/opam
index 9441ca2b527..08abf4b5138 100644
--- a/packages/conf-liblz4/conf-liblz4.1/opam
+++ b/packages/conf-liblz4/conf-liblz4.1/opam
@@ -5,9 +5,9 @@ bug-reports: "https://github.com/ocaml/opam-repository/issues"
 authors: ["Yann Collet"]
 license: ["GPL-2.0-only" "BSD-2-Clause"]
 build: [
-  ["pkgconf" "--personality=i686-w64-mingw32" "liblz4"] {os = "win32" & os-distribution = "cygwin" & host-arch-x86_32:installed}
-  ["pkgconf" "--personality=x86_64-w64-mingw32" "liblz4"] {os = "win32" & os-distribution = "cygwin" & host-arch-x86_64:installed}
-  ["pkg-config" "liblz4"] {os != "win32" | os-distribution != "cygwin"}
+  ["pkgconf" "--personality=i686-w64-mingw32" "liblz4"] {os = "win32" & os-distribution != "cygwinports" & host-arch-x86_32:installed}
+  ["pkgconf" "--personality=x86_64-w64-mingw32" "liblz4"] {os = "win32" & os-distribution != "cygwinports" & host-arch-x86_64:installed}
+  ["pkg-config" "liblz4"] {os != "win32" | os-distribution = "cygwinports"}
 ]
 depends: [
   "conf-pkg-config" {build}
diff --git a/packages/conf-libpcre/conf-libpcre.2/opam b/packages/conf-libpcre/conf-libpcre.2/opam
index e4a7bdba85f..3d0bfd102d2 100644
--- a/packages/conf-libpcre/conf-libpcre.2/opam
+++ b/packages/conf-libpcre/conf-libpcre.2/opam
@@ -8,15 +8,15 @@ homepage: "http://www.pcre.org/"
 dev-repo: "git+https://github.com/mmottl/pcre-ocaml.git"
 license: "BSD-3-Clause"
 build:
-  ["pkgconf" {os = "win32" & os-distribution = "cygwin"}
-   "--personality=i686-w64-mingw32" {os = "win32" & os-distribution = "cygwin" & host-arch-x86_32:installed}
-   "--personality=x86_64-w64-mingw32" {os = "win32" & os-distribution = "cygwin" & host-arch-x86_64:installed}
-   "pkg-config" {os != "win32" | os-distribution != "cygwin"}
+  ["pkgconf" {os = "win32" & os-distribution != "cygwinports"}
+   "--personality=i686-w64-mingw32" {os = "win32" & os-distribution != "cygwinports" & host-arch-x86_32:installed}
+   "--personality=x86_64-w64-mingw32" {os = "win32" & os-distribution != "cygwinports" & host-arch-x86_64:installed}
+   "pkg-config" {os != "win32" | os-distribution = "cygwinports"}
    "--print-errors" "--exists" "libpcre"]
 depends: [
  "conf-pkg-config" {build}
-  ("host-arch-x86_32" {os = "win32" & os-distribution = "cygwin"} & "conf-mingw-w64-pcre-i686" {os = "win32" & os-distribution = "cygwin"} |
-   "host-arch-x86_64" {os = "win32" & os-distribution = "cygwin"} & "conf-mingw-w64-pcre-x86_64" {os = "win32" & os-distribution = "cygwin"})
+  ("host-arch-x86_32" {os = "win32" & os-distribution != "cygwinports"} & "conf-mingw-w64-pcre-i686" {os = "win32" & os-distribution != "cygwinports"} |
+   "host-arch-x86_64" {os = "win32" & os-distribution != "cygwinports"} & "conf-mingw-w64-pcre-x86_64" {os = "win32" & os-distribution != "cygwinports"})
  ]
 bug-reports: "https://github.com/ocaml/opam-repository/issues"
 depexts: [
diff --git a/packages/conf-libpcre2-8/conf-libpcre2-8.2/opam b/packages/conf-libpcre2-8/conf-libpcre2-8.2/opam
index cf9f64fa64a..c9b2410e7f0 100644
--- a/packages/conf-libpcre2-8/conf-libpcre2-8.2/opam
+++ b/packages/conf-libpcre2-8/conf-libpcre2-8.2/opam
@@ -8,10 +8,10 @@ homepage: "https://www.pcre.org/"
 dev-repo: "git+https://github.com/PCRE2Project/pcre2.git"
 license: "BSD-3-Clause"
 build: [
-  ["pkgconf" {os = "win32" & os-distribution = "cygwin"}
-   "--personality=i686-w64-mingw32" {os = "win32" & os-distribution = "cygwin" & host-arch-x86_32:installed}
-   "--personality=x86_64-w64-mingw32" {os = "win32" & os-distribution = "cygwin" & host-arch-x86_64:installed}
-   "pkg-config" {os != "win32" | os-distribution != "cygwin"}
+  ["pkgconf" {os = "win32" & os-distribution != "cygwinports"}
+   "--personality=i686-w64-mingw32" {os = "win32" & os-distribution != "cygwinports" & host-arch-x86_32:installed}
+   "--personality=x86_64-w64-mingw32" {os = "win32" & os-distribution != "cygwinports" & host-arch-x86_64:installed}
+   "pkg-config" {os != "win32" | os-distribution = "cygwinports"}
    "--print-errors" "--exists" "libpcre2-8"
   ]]
 depends: [
diff --git a/packages/conf-libssl/conf-libssl.4/opam b/packages/conf-libssl/conf-libssl.4/opam
index 7f0f2ed8185..ba725bb3d17 100644
--- a/packages/conf-libssl/conf-libssl.4/opam
+++ b/packages/conf-libssl/conf-libssl.4/opam
@@ -8,10 +8,10 @@ build-env: [
   [HOMEBREW_NO_AUTO_UPDATE = "1"]
 ]
 build: [
-  ["pkgconf" {os = "win32" & os-distribution = "cygwin"}
-   "--personality=i686-w64-mingw32" {os = "win32" & os-distribution = "cygwin" & host-arch-x86_32:installed}
-   "--personality=x86_64-w64-mingw32" {os = "win32" & os-distribution = "cygwin" & host-arch-x86_64:installed}
-   "pkg-config" {os != "win32" | os-distribution != "cygwin"}
+  ["pkgconf" {os = "win32" & os-distribution != "cygwinports"}
+   "--personality=i686-w64-mingw32" {os = "win32" & os-distribution != "cygwinports" & host-arch-x86_32:installed}
+   "--personality=x86_64-w64-mingw32" {os = "win32" & os-distribution != "cygwinports" & host-arch-x86_64:installed}
+   "pkg-config" {os != "win32" | os-distribution = "cygwinports"}
    "--print-errors" "--exists" "openssl"]
     {os != "freebsd" & os != "openbsd" & os != "netbsd" & # libssl is provided by base system on BSDs
      os-distribution != "homebrew"}
diff --git a/packages/conf-mingw-w64-ncurses-i686/conf-mingw-w64-ncurses-i686.1/opam b/packages/conf-mingw-w64-ncurses-i686/conf-mingw-w64-ncurses-i686.1/opam
index f32ef03f3aa..4fbca8820c6 100644
--- a/packages/conf-mingw-w64-ncurses-i686/conf-mingw-w64-ncurses-i686.1/opam
+++ b/packages/conf-mingw-w64-ncurses-i686/conf-mingw-w64-ncurses-i686.1/opam
@@ -5,7 +5,10 @@ bug-reports: "https://github.com/ocaml/opam-repository/issues"
 license: "MIT"
 flags: conf
 available: os = "win32"
-build: ["pkgconf" "--personality=i686-w64-mingw32" "ncurses"]
+build: ["pkgconf" "--personality=i686-w64-mingw32"
+        "ncurses"  {os-distribution = "cygwin"}
+        "ncursesw" {os-distribution = "msys2"}
+]
 depends: [
   "conf-pkg-config" {build}
   "conf-mingw-w64-gcc-i686" {build}
diff --git a/packages/conf-mingw-w64-ncurses-x86_64/conf-mingw-w64-ncurses-x86_64.1/opam b/packages/conf-mingw-w64-ncurses-x86_64/conf-mingw-w64-ncurses-x86_64.1/opam
index 4556c3bf7c9..e300d7321aa 100644
--- a/packages/conf-mingw-w64-ncurses-x86_64/conf-mingw-w64-ncurses-x86_64.1/opam
+++ b/packages/conf-mingw-w64-ncurses-x86_64/conf-mingw-w64-ncurses-x86_64.1/opam
@@ -5,7 +5,10 @@ bug-reports: "https://github.com/ocaml/opam-repository/issues"
 license: "MIT"
 flags: conf
 available: os = "win32"
-build: ["pkgconf" "--personality=x86_64-w64-mingw32" "ncurses"]
+build: ["pkgconf" "--personality=x86_64-w64-mingw32"
+        "ncurses"  {os-distribution = "cygwin"}
+        "ncursesw" {os-distribution = "msys2"}
+]
 depends: [
   "conf-pkg-config" {build}
   "conf-mingw-w64-gcc-x86_64" {build}
diff --git a/packages/conf-mingw-w64-pcre-i686/conf-mingw-w64-pcre-i686.1/opam b/packages/conf-mingw-w64-pcre-i686/conf-mingw-w64-pcre-i686.1/opam
index f47cf1212c0..489e7c09560 100644
--- a/packages/conf-mingw-w64-pcre-i686/conf-mingw-w64-pcre-i686.1/opam
+++ b/packages/conf-mingw-w64-pcre-i686/conf-mingw-w64-pcre-i686.1/opam
@@ -10,7 +10,7 @@ license: "BSD-3-Clause"
 homepage: "https://www.pcre.org/"
 bug-reports: "https://github.com/ocaml/opam-repository/issues"
 flags: conf
-available: os = "win32" & os-distribution = "cygwin"
+available: os = "win32"
 build: ["pkgconf" "--personality=i686-w64-mingw32" "libpcre"]
 depends: [
   "conf-pkg-config" {build}
diff --git a/packages/conf-mingw-w64-pcre-x86_64/conf-mingw-w64-pcre-x86_64.1/opam b/packages/conf-mingw-w64-pcre-x86_64/conf-mingw-w64-pcre-x86_64.1/opam
index aa75fd675da..aafb54d2eae 100644
--- a/packages/conf-mingw-w64-pcre-x86_64/conf-mingw-w64-pcre-x86_64.1/opam
+++ b/packages/conf-mingw-w64-pcre-x86_64/conf-mingw-w64-pcre-x86_64.1/opam
@@ -10,7 +10,7 @@ license: "BSD-3-Clause"
 homepage: "https://www.pcre.org/"
 bug-reports: "https://github.com/ocaml/opam-repository/issues"
 flags: conf
-available: os = "win32" & os-distribution = "cygwin"
+available: os = "win32"
 build: ["pkgconf" "--personality=x86_64-w64-mingw32" "libpcre"]
 depends: [
   "conf-pkg-config" {build}
diff --git a/packages/conf-ncurses/conf-ncurses.1/opam b/packages/conf-ncurses/conf-ncurses.1/opam
index 17d4a31f6b0..55d63acab34 100644
--- a/packages/conf-ncurses/conf-ncurses.1/opam
+++ b/packages/conf-ncurses/conf-ncurses.1/opam
@@ -12,8 +12,9 @@ build: [
   "--personality=x86_64-w64-mingw32"
     {os = "win32" & os-distribution != "cygwinports" &
      host-arch-x86_64:installed}
-  "pkg-config" {os-distribution != "cygwin" & os-distribution != "opensuse" & os != "macos" & os != "freebsd" & os != "netbsd" & os != "openbsd"}
-  "ncurses" {os-distribution != "opensuse" & os != "macos" & os != "freebsd" & os != "netbsd" & os != "openbsd"}
+  "pkg-config" {os-distribution != "cygwin" & os-distribution != "msys2" & os-distribution != "opensuse" & os != "macos" & os != "freebsd" & os != "netbsd" & os != "openbsd"}
+  "ncurses" {os-distribution != "opensuse" & os != "macos" & os != "freebsd" & os != "netbsd" & os != "openbsd" & os-distribution != "msys2"}
+  "ncursesw" {os-distribution = "msys2"} # MSys2 packages compatible ncursesw https://packages.msys2.org/packages/mingw-w64-x86_64-ncurses
 ]
 depends: [
   "conf-pkg-config" {build & os-distribution != "opensuse" & os != "macos" & os != "freebsd" & os != "netbsd" & os != "openbsd"}