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+;;; my-org-unfill-aware.el --- Org-aware hard line break remover -*- lexical-binding: t; -*-
+
+;; Author: Takahiro Ohkubo / ChatGPT
+;; Version: 0.1
+;; Keywords: org, text, clipboard
+;;
+;; This file provides Org-aware functions to remove hard line breaks
+;; from normal paragraphs while preserving Org structures such as
+;; headings, lists, tables, source/example/export blocks, drawers,
+;; comments, horizontal rules, and display math lines.
+
+(require 'cl-lib)
+(require 'subr-x)
+
+(defgroup my-org-unfill-aware nil
+  "Org-aware hard line break removal."
+  :group 'org
+  :prefix "my-org-unfill-aware-")
+
+(defcustom my-org-unfill-aware-preserve-list-items t
+  "If non-nil, preserve list item lines as structural lines.
+Continuation lines after a list item are still treated as normal paragraph
+text unless they also match a preserved Org structure."
+  :type 'boolean
+  :group 'my-org-unfill-aware)
+
+(defun my-org-unfill-aware--region-or-buffer ()
+  "Return region bounds if active, otherwise whole buffer bounds."
+  (if (use-region-p)
+      (list (region-beginning) (region-end))
+    (list (point-min) (point-max))))
+
+(defun my-org-unfill-aware--japanese-p (text)
+  "Return non-nil if TEXT contains Japanese/CJK characters."
+  (string-match-p "[ぁ-んァ-ン一-龯々〆〤ー]" text))
+
+(defun my-org-unfill-aware--ascii-normalize-space (s)
+  "Normalize whitespace in ASCII paragraph S."
+  (string-trim
+   (replace-regexp-in-string "[ \t\n]+" " " s)))
+
+(defun my-org-unfill-aware--join-lines (lines joiner ascii-p)
+  "Join paragraph LINES using JOINER.
+If ASCII-P is non-nil, normalize multiple spaces into one."
+  (let ((s (mapconcat #'string-trim lines joiner)))
+    (if ascii-p
+        (my-org-unfill-aware--ascii-normalize-space s)
+      (string-trim s))))
+
+(defun my-org-unfill-aware--blank-line-p (line)
+  "Return non-nil if LINE is blank."
+  (string-match-p "\\`[ \t]*\\'" line))
+
+(defun my-org-unfill-aware--heading-p (line)
+  "Return non-nil if LINE is an Org heading."
+  (string-match-p "\\`[ \t]*\\*+\\s-+" line))
+
+(defun my-org-unfill-aware--keyword-p (line)
+  "Return non-nil if LINE is an Org keyword line."
+  (string-match-p "\\`[ \t]*#\\+[-A-Za-z0-9_]+:" line))
+
+(defun my-org-unfill-aware--comment-p (line)
+  "Return non-nil if LINE is an Org comment line."
+  (string-match-p "\\`[ \t]*#\\($\\|[^+]\\)" line))
+
+(defun my-org-unfill-aware--table-p (line)
+  "Return non-nil if LINE is an Org table line."
+  (string-match-p "\\`[ \t]*|" line))
+
+(defun my-org-unfill-aware--hline-p (line)
+  "Return non-nil if LINE is an Org horizontal rule."
+  (string-match-p "\\`[ \t]*-----+[ \t]*\\'" line))
+
+(defun my-org-unfill-aware--drawer-begin-p (line)
+  "Return non-nil if LINE begins an Org drawer."
+  (string-match-p "\\`[ \t]*:[A-Za-z0-9_-]+:[ \t]*\\'" line))
+
+(defun my-org-unfill-aware--drawer-end-p (line)
+  "Return non-nil if LINE ends an Org drawer."
+  (string-match-p "\\`[ \t]*:END:[ \t]*\\'" line))
+
+(defun my-org-unfill-aware--list-item-p (line)
+  "Return non-nil if LINE looks like an Org list item."
+  (and my-org-unfill-aware-preserve-list-items
+       (string-match-p
+        "\\`[ \t]*\\(?:[-+]\\|[0-9]+[.)]\\|[A-Za-z][.)]\\)\\s-+"
+        line)))
+
+(defun my-org-unfill-aware--display-math-p (line)
+  "Return non-nil if LINE looks like display math delimiter/content."
+  (string-match-p
+   "\\`[ \t]*\\(?:\\\\\\[\\|\\\\\\]\\|\\\\begin{\\|\\\\end{\\|\\$\\$\\)"
+   line))
+
+(defun my-org-unfill-aware--block-begin-p (line)
+  "Return non-nil if LINE begins an Org block."
+  (string-match-p "\\`[ \t]*#\\+BEGIN_" (upcase line)))
+
+(defun my-org-unfill-aware--block-end-p (line)
+  "Return non-nil if LINE ends an Org block."
+  (string-match-p "\\`[ \t]*#\\+END_" (upcase line)))
+
+(defun my-org-unfill-aware--structural-line-p (line)
+  "Return non-nil if LINE should not be joined with surrounding text."
+  (or (my-org-unfill-aware--blank-line-p line)
+      (my-org-unfill-aware--heading-p line)
+      (my-org-unfill-aware--keyword-p line)
+      (my-org-unfill-aware--comment-p line)
+      (my-org-unfill-aware--table-p line)
+      (my-org-unfill-aware--hline-p line)
+      (my-org-unfill-aware--drawer-begin-p line)
+      (my-org-unfill-aware--drawer-end-p line)
+      (my-org-unfill-aware--list-item-p line)
+      (my-org-unfill-aware--display-math-p line)))
+
+(defun my-org-unfill-aware--process-text (text joiner ascii-p)
+  "Return processed TEXT using JOINER.
+If ASCII-P is non-nil, normalize spaces in joined paragraphs."
+  (let ((lines (split-string text "\n"))
+        (out nil)
+        (para nil)
+        (in-block nil)
+        (in-drawer nil))
+    (cl-labels
+        ((flush-para
+          ()
+          (when para
+            (push (my-org-unfill-aware--join-lines
+                   (nreverse para) joiner ascii-p)
+                  out)
+            (setq para nil))))
+      (dolist (line lines)
+        (cond
+         ;; Inside source/example/export/special block: preserve literally.
+         (in-block
+          (flush-para)
+          (push line out)
+          (when (my-org-unfill-aware--block-end-p line)
+            (setq in-block nil)))
+
+         ;; Inside drawer/properties: preserve literally.
+         (in-drawer
+          (flush-para)
+          (push line out)
+          (when (my-org-unfill-aware--drawer-end-p line)
+            (setq in-drawer nil)))
+
+         ;; Begin block.
+         ((my-org-unfill-aware--block-begin-p line)
+          (flush-para)
+          (push line out)
+          (setq in-block t))
+
+         ;; Begin drawer.
+         ((my-org-unfill-aware--drawer-begin-p line)
+          (flush-para)
+          (push line out)
+          (unless (my-org-unfill-aware--drawer-end-p line)
+            (setq in-drawer t)))
+
+         ;; Other structural line.
+         ((my-org-unfill-aware--structural-line-p line)
+          (flush-para)
+          (push line out))
+
+         ;; Normal paragraph line.
+         (t
+          (push line para))))
+      (flush-para))
+    (mapconcat #'identity (nreverse out) "\n")))
+
+(defun my-org-unfill-aware--replace-region (beg end joiner ascii-p)
+  "Replace region BEG END with Org-aware unfilled text."
+  (let ((new-text
+         (my-org-unfill-aware--process-text
+          (buffer-substring-no-properties beg end)
+          joiner ascii-p)))
+    (delete-region beg end)
+    (insert new-text)))
+
+;;;###autoload
+(defun my-org-unfill-aware-ascii (beg end)
+  "Org-aware ASCII mode.
+Remove hard line breaks in normal paragraphs by replacing them with one space.
+Org structures are preserved."
+  (interactive (my-org-unfill-aware--region-or-buffer))
+  (my-org-unfill-aware--replace-region beg end " " t))
+
+;;;###autoload
+(defun my-org-unfill-aware-japanese (beg end)
+  "Org-aware Japanese mode.
+Remove hard line breaks in normal paragraphs without inserting spaces.
+Org structures are preserved."
+  (interactive (my-org-unfill-aware--region-or-buffer))
+  (my-org-unfill-aware--replace-region beg end "" nil))
+
+;;;###autoload
+(defun my-org-unfill-aware-auto (beg end)
+  "Org-aware auto mode.
+If the selected text contains Japanese/CJK characters, use Japanese mode.
+Otherwise use ASCII mode."
+  (interactive (my-org-unfill-aware--region-or-buffer))
+  (let ((text (buffer-substring-no-properties beg end)))
+    (if (my-org-unfill-aware--japanese-p text)
+        (my-org-unfill-aware-japanese beg end)
+      (my-org-unfill-aware-ascii beg end))))
+
+(defun my-org-unfill-aware--copy-only (beg end fn)
+  "Copy processed text from BEG END using FN without modifying current buffer."
+  (let* ((text (buffer-substring-no-properties beg end))
+         (buf (generate-new-buffer " *my-org-unfill-aware-copy*")))
+    (unwind-protect
+        (with-current-buffer buf
+          (insert text)
+          (funcall fn (point-min) (point-max))
+          (kill-new (buffer-string)))
+      (kill-buffer buf))
+    (message "Org-aware unfilled text copied to kill-ring.")))
+
+;;;###autoload
+(defun my-org-unfill-aware-ascii-copy (beg end)
+  "Org-aware ASCII mode, copy only.
+Do not modify current buffer."
+  (interactive (my-org-unfill-aware--region-or-buffer))
+  (my-org-unfill-aware--copy-only beg end #'my-org-unfill-aware-ascii))
+
+;;;###autoload
+(defun my-org-unfill-aware-japanese-copy (beg end)
+  "Org-aware Japanese mode, copy only.
+Do not modify current buffer."
+  (interactive (my-org-unfill-aware--region-or-buffer))
+  (my-org-unfill-aware--copy-only beg end #'my-org-unfill-aware-japanese))
+
+;;;###autoload
+(defun my-org-unfill-aware-auto-copy (beg end)
+  "Org-aware auto mode, copy only.
+Do not modify current buffer."
+  (interactive (my-org-unfill-aware--region-or-buffer))
+  (my-org-unfill-aware--copy-only beg end #'my-org-unfill-aware-auto))
+
+(provide 'my-org-unfill-aware)
+;;; my-org-unfill-aware.el ends here