When I use plstore with gnupg (from either Cygwin or directly the Windows version), plstore does not correctly decrypt. The reason seems to be that spurious carriage return characters are added when encrypting the plstore file. When later decrypting it, these carriage returns make gnupg fail. This issue can be reproduced by opening a plstore file in plstore-mode and encrypting and decrypting it repeatedly via C-c C-c. The added carriage returns are directly visible. The error also affects other packages that use the plstore. A quick workaround for me was to add an advice that removes the carriage returns (here ^M needs to be replaced by the carriage return character): (defun rg/plstore--init-from-buffer-advice (orig-fun &rest plstore) (goto-char (point-min)) (save-match-data (let ((inhibit-modification-hooks t)) (while (re-search-forward "^M" nil t) (replace-match "")))) (save-buffer) (apply orig-fun plstore)) (advice-add 'plstore--init-from-buffer :around #'rg/plstore--init-from-buffer-advice)) In GNU Emacs 25.2.1 (x86_64-w64-mingw32) of 2017-04-24 built on KAEL Repository revision: 784602b10506c50075aa9463891a47380ebea55f Windowing system distributor 'Microsoft Corp.', version 10.0.15063 Configured using: 'configure --prefix=/tmp/emacs --without-imagemagick --without-dbus --with-modules 'CFLAGS=-O2 -fomit-frame-pointer -g0'' Configured features: XPM JPEG TIFF GIF PNG RSVG SOUND NOTIFY ACL GNUTLS LIBXML2 ZLIB TOOLKIT_SCROLL_BARS MODULES Important settings: value of $LANG: DEU locale-coding-system: cp1252 Major mode: Emacs-Lisp Minor modes in effect: hi-lock-mode: t highlight-thing-mode: t rainbow-delimiters-mode: t show-smartparens-global-mode: t show-smartparens-mode: t smartparens-global-mode: t smartparens-mode: t global-hl-line-mode: t company-quickhelp-mode: t company-quickhelp-local-mode: t global-company-mode: t company-mode: t persistent-scratch-autosave-mode: t flyspell-lazy-mode: t ivy-mode: t delete-selection-mode: t recentf-mode: t display-time-mode: t auto-compile-on-load-mode: t override-global-mode: t tooltip-mode: t global-eldoc-mode: t electric-indent-mode: t mouse-wheel-mode: t file-name-shadow-mode: t global-font-lock-mode: t font-lock-mode: t blink-cursor-mode: t auto-composition-mode: t auto-encryption-mode: t auto-compression-mode: t column-number-mode: t line-number-mode: t transient-mark-mode: t Recent messages: Matches: \\(?:[/ ][-+]?[0-9]+[hdwmy]\\)?\\)" user-error: Cannot enlarge selected window Undo! 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