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I use mu4e to handle my 3 email accounts - Exchange, Posteo, Gmail. While I have no problem sending emails with Exchange and Posteo, I encounter the following issue when sending via Gmail:

Debugger entered--Lisp error: (error "Sending failed: 535-5.7.8 Username and Password not accepted. Learn more at\n535 5.7.8  https://support.google.com/mail/?p=BadCredentials c207sm5903330pfb.47 - gsmtp in response to AUTH")
  signal(error ("Sending failed: 535-5.7.8 Username and Password not accepted. Learn more at\n535 5.7.8  https://support.google.com/mail/?p=BadCredentials c207sm5903330pfb.47 - gsmtp in response to AUTH"))
  error("Sending failed: %s" "535-5.7.8 Username and Password not accepted. Learn more at\n535 5.7.8  https://support.google.com/mail/?p=BadCredentials c207sm5903330pfb.47 - gsmtp in response to AUTH")
  smtpmail-send-it()
  message-use-send-mail-function()
  message--default-send-mail-function()
  message-multi-smtp-send-mail()
  message--send-mail-maybe-partially()
  message-send-mail(nil)
  message-send-via-mail(nil)
  message-send(nil)
  message-send-and-exit()
  org-msg-ctrl-c-ctrl-c()
  run-hook-with-args-until-success(org-msg-ctrl-c-ctrl-c)
  (cond ((memq type '(src-block inline-src-block)) (if org-babel-no-eval-on-ctrl-c-ctrl-c nil (org-babel-eval-wipe-error-buffer) (org-babel-execute-src-block current-prefix-arg (org-babel-get-src-block-info nil context)))) ((org-match-line "[ \11]*$") (or (run-hook-with-args-until-success 'org-ctrl-c-ctrl-c-final-hook) (user-error (substitute-command-keys "`\\[org-ctrl-c-ctrl-c]' can do nothing useful...")))) ((memq type '(inline-babel-call babel-call)) (let ((info (org-babel-lob-get-info context))) (if info (progn (org-babel-execute-src-block nil info))))) ((eq type 'clock) (org-clock-update-time-maybe)) ((eq type 'dynamic-block) (save-excursion (goto-char (org-element-property :post-affiliated context)) (org-update-dblock))) ((eq type 'footnote-definition) (goto-char (org-element-property :post-affiliated context)) (call-interactively 'org-footnote-action)) ((eq type 'footnote-reference) (call-interactively #'org-footnote-action)) ((memq type '(inlinetask headline)) (save-excursion (goto-char (org-element-property :begin context)) (call-interactively #'org-set-tags-command))) ((eq type 'item) (let* ((box (org-element-property :checkbox context)) (struct (org-element-property :structure context)) (old-struct (copy-tree struct)) (parents (org-list-parents-alist struct)) (prevs (org-list-prevs-alist struct)) (orderedp (org-not-nil (org-entry-get nil "ORDERED")))) (org-list-set-checkbox (org-element-property :begin context) struct (cond ((equal arg ...) "[-]") ((and ... ...) "[ ]") ((or ... ...) nil) ((eq box ...) "[ ]") (t "[X]"))) (org-list-struct-fix-ind struct parents 2) (org-list-struct-fix-item-end struct) (org-list-struct-fix-bul struct prevs) (org-list-struct-fix-ind struct parents) (let ((block-item (org-list-struct-fix-box struct parents prevs orderedp))) (if (and box (equal struct old-struct)) (if (equal arg ...) (message "Checkboxes already reset") (user-error "Cannot toggle this checkbox: %s" ...)) (org-list-struct-apply-struct struct old-struct) (org-update-checkbox-count-maybe)) (if block-item (progn (message "Checkboxes were removed due to empty box at ..." ...)))))) ((eq type 'keyword) (let ((org-inhibit-startup-visibility-stuff t) (org-startup-align-all-tables nil)) (if (boundp 'org-table-coordinate-overlays) (progn (mapc #'delete-overlay org-table-coordinate-overlays) (setq org-table-coordinate-overlays nil))) (let* ((--invisible-types '...) (--markers\? 'use-markers) (--data (mapcar ... ...))) (unwind-protect (progn (org-mode-restart)) (save-excursion (save-restriction ... ... ...))))) (message "Local setup has been refreshed")) ((eq type 'plain-list) (let* ((begin (org-element-property :contents-begin context)) (struct (org-element-property :structure context)) (old-struct (copy-tree struct)) (first-box (save-excursion (goto-char begin) (looking-at org-list-full-item-re) (match-string-no-properties 3))) (new-box (cond (... "[-]") (... ...) (... "[ ]") (t "[X]")))) (cond (arg (let (...) (while --dolist-tail-- ...))) ((and first-box (eq ... begin)) (org-list-set-checkbox begin struct new-box))) (if (equal (org-list-write-struct struct (org-list-parents-alist struct) old-struct) old-struct) (progn (message "Cannot update this checkbox"))) (org-update-checkbox-count-maybe))) ((memq type '(node-property property-drawer)) (call-interactively #'org-property-action)) ((eq type 'radio-target) (call-interactively #'org-update-radio-target-regexp)) ((eq type 'statistics-cookie) (call-interactively #'org-update-statistics-cookies)) ((memq type '(table-row table-cell table)) (if (eq (org-element-property :type context) 'table\.el) (message "%s" (substitute-command-keys "\\<org-mode-map>Use `\\[org-edit-special]' to ...")) (if (or (eq type 'table) (and (eq type ...) (= ... ...))) (save-excursion (if (org-at-TBLFM-p) (progn ... ...) (goto-char ...) (org-call-with-arg ... ...) (orgtbl-send-table ...))) (org-table-maybe-eval-formula) (cond (arg (call-interactively ...)) ((org-table-maybe-recalculate-line)) (t (org-table-align)))))) ((eq type 'timestamp) (funcall pcase-0)) ((eq type 'planning) (cond ((org-at-timestamp-p 'lax) (funcall pcase-0)) ((run-hook-with-args-until-success 'org-ctrl-c-ctrl-c-final-hook) nil) (t (user-error (substitute-command-keys "`\\[org-ctrl-c-ctrl-c]' can do nothing useful..."))))) ((null type) (cond ((org-at-heading-p) (call-interactively #'org-set-tags-command)) ((run-hook-with-args-until-success 'org-ctrl-c-ctrl-c-final-hook) (funcall pcase-1)) (t (funcall pcase-2)))) ((run-hook-with-args-until-success 'org-ctrl-c-ctrl-c-final-hook) (funcall pcase-1)) (t (funcall pcase-2)))
  (let* ((pcase-2 #'(lambda nil (user-error (substitute-command-keys "`\\[org-ctrl-c-ctrl-c]' can do nothing useful here")))) (pcase-1 #'(lambda nil)) (pcase-0 #'(lambda nil (org-timestamp-change 0 'day)))) (cond ((memq type '(src-block inline-src-block)) (if org-babel-no-eval-on-ctrl-c-ctrl-c nil (org-babel-eval-wipe-error-buffer) (org-babel-execute-src-block current-prefix-arg (org-babel-get-src-block-info nil context)))) ((org-match-line "[ \11]*$") (or (run-hook-with-args-until-success 'org-ctrl-c-ctrl-c-final-hook) (user-error (substitute-command-keys "`\\[org-ctrl-c-ctrl-c]' can do nothing useful here")))) ((memq type '(inline-babel-call babel-call)) (let ((info (org-babel-lob-get-info context))) (if info (progn (org-babel-execute-src-block nil info))))) ((eq type 'clock) (org-clock-update-time-maybe)) ((eq type 'dynamic-block) (save-excursion (goto-char (org-element-property :post-affiliated context)) (org-update-dblock))) ((eq type 'footnote-definition) (goto-char (org-element-property :post-affiliated context)) (call-interactively 'org-footnote-action)) ((eq type 'footnote-reference) (call-interactively #'org-footnote-action)) ((memq type '(inlinetask headline)) (save-excursion (goto-char (org-element-property :begin context)) (call-interactively #'org-set-tags-command))) ((eq type 'item) (let* ((box (org-element-property :checkbox context)) (struct (org-element-property :structure context)) (old-struct (copy-tree struct)) (parents (org-list-parents-alist struct)) (prevs (org-list-prevs-alist struct)) (orderedp (org-not-nil (org-entry-get nil "ORDERED")))) (org-list-set-checkbox (org-element-property :begin context) struct (cond ((equal arg ...) "[-]") ((and ... ...) "[ ]") ((or ... ...) nil) ((eq box ...) "[ ]") (t "[X]"))) (org-list-struct-fix-ind struct parents 2) (org-list-struct-fix-item-end struct) (org-list-struct-fix-bul struct prevs) (org-list-struct-fix-ind struct parents) (let ((block-item (org-list-struct-fix-box struct parents prevs orderedp))) (if (and box (equal struct old-struct)) (if (equal arg ...) (message "Checkboxes already reset") (user-error "Cannot toggle this checkbox: %s" ...)) (org-list-struct-apply-struct struct old-struct) (org-update-checkbox-count-maybe)) (if block-item (progn (message "Checkboxes were removed due to empty box at line %..." ...)))))) ((eq type 'keyword) (let ((org-inhibit-startup-visibility-stuff t) (org-startup-align-all-tables nil)) (if (boundp 'org-table-coordinate-overlays) (progn (mapc #'delete-overlay org-table-coordinate-overlays) (setq org-table-coordinate-overlays nil))) (let* ((--invisible-types '...) (--markers\? 'use-markers) (--data (mapcar ... ...))) (unwind-protect (progn (org-mode-restart)) (save-excursion (save-restriction ... ... ...))))) (message "Local setup has been refreshed")) ((eq type 'plain-list) (let* ((begin (org-element-property :contents-begin context)) (struct (org-element-property :structure context)) (old-struct (copy-tree struct)) (first-box (save-excursion (goto-char begin) (looking-at org-list-full-item-re) (match-string-no-properties 3))) (new-box (cond (... "[-]") (... ...) (... "[ ]") (t "[X]")))) (cond (arg (let (...) (while --dolist-tail-- ...))) ((and first-box (eq ... begin)) (org-list-set-checkbox begin struct new-box))) (if (equal (org-list-write-struct struct (org-list-parents-alist struct) old-struct) old-struct) (progn (message "Cannot update this checkbox"))) (org-update-checkbox-count-maybe))) ((memq type '(node-property property-drawer)) (call-interactively #'org-property-action)) ((eq type 'radio-target) (call-interactively #'org-update-radio-target-regexp)) ((eq type 'statistics-cookie) (call-interactively #'org-update-statistics-cookies)) ((memq type '(table-row table-cell table)) (if (eq (org-element-property :type context) 'table\.el) (message "%s" (substitute-command-keys "\\<org-mode-map>Use `\\[org-edit-special]' to edit t...")) (if (or (eq type 'table) (and (eq type ...) (= ... ...))) (save-excursion (if (org-at-TBLFM-p) (progn ... ...) (goto-char ...) (org-call-with-arg ... ...) (orgtbl-send-table ...))) (org-table-maybe-eval-formula) (cond (arg (call-interactively ...)) ((org-table-maybe-recalculate-line)) (t (org-table-align)))))) ((eq type 'timestamp) (funcall pcase-0)) ((eq type 'planning) (cond ((org-at-timestamp-p 'lax) (funcall pcase-0)) ((run-hook-with-args-until-success 'org-ctrl-c-ctrl-c-final-hook) nil) (t (user-error (substitute-command-keys "`\\[org-ctrl-c-ctrl-c]' can do nothing useful here"))))) ((null type) (cond ((org-at-heading-p) (call-interactively #'org-set-tags-command)) ((run-hook-with-args-until-success 'org-ctrl-c-ctrl-c-final-hook) (funcall pcase-1)) (t (funcall pcase-2)))) ((run-hook-with-args-until-success 'org-ctrl-c-ctrl-c-final-hook) (funcall pcase-1)) (t (funcall pcase-2))))
  (let* ((context (org-element-lineage (org-element-context) '(babel-call clock dynamic-block footnote-definition footnote-reference inline-babel-call inline-src-block inlinetask item keyword node-property paragraph plain-list planning property-drawer radio-target src-block statistics-cookie table table-cell table-row timestamp) t)) (type (org-element-type context))) (if (eq type 'paragraph) (progn (let ((parent (org-element-property :parent context))) (if (and (eq (org-element-type parent) 'item) (= (line-beginning-position) (org-element-property :begin parent))) (progn (setq context parent) (setq type 'item)))))) (let* ((pcase-2 #'(lambda nil (user-error (substitute-command-keys "`\\[org-ctrl-c-ctrl-c]' can do nothing useful here")))) (pcase-1 #'(lambda nil)) (pcase-0 #'(lambda nil (org-timestamp-change 0 'day)))) (cond ((memq type '(src-block inline-src-block)) (if org-babel-no-eval-on-ctrl-c-ctrl-c nil (org-babel-eval-wipe-error-buffer) (org-babel-execute-src-block current-prefix-arg (org-babel-get-src-block-info nil context)))) ((org-match-line "[ \11]*$") (or (run-hook-with-args-until-success 'org-ctrl-c-ctrl-c-final-hook) (user-error (substitute-command-keys "`\\[org-ctrl-c-ctrl-c]' can do nothing useful here")))) ((memq type '(inline-babel-call babel-call)) (let ((info (org-babel-lob-get-info context))) (if info (progn (org-babel-execute-src-block nil info))))) ((eq type 'clock) (org-clock-update-time-maybe)) ((eq type 'dynamic-block) (save-excursion (goto-char (org-element-property :post-affiliated context)) (org-update-dblock))) ((eq type 'footnote-definition) (goto-char (org-element-property :post-affiliated context)) (call-interactively 'org-footnote-action)) ((eq type 'footnote-reference) (call-interactively #'org-footnote-action)) ((memq type '(inlinetask headline)) (save-excursion (goto-char (org-element-property :begin context)) (call-interactively #'org-set-tags-command))) ((eq type 'item) (let* ((box (org-element-property :checkbox context)) (struct (org-element-property :structure context)) (old-struct (copy-tree struct)) (parents (org-list-parents-alist struct)) (prevs (org-list-prevs-alist struct)) (orderedp (org-not-nil ...))) (org-list-set-checkbox (org-element-property :begin context) struct (cond (... "[-]") (... "[ ]") (... nil) (... "[ ]") (t "[X]"))) (org-list-struct-fix-ind struct parents 2) (org-list-struct-fix-item-end struct) (org-list-struct-fix-bul struct prevs) (org-list-struct-fix-ind struct parents) (let ((block-item ...)) (if (and box ...) (if ... ... ...) (org-list-struct-apply-struct struct old-struct) (org-update-checkbox-count-maybe)) (if block-item (progn ...))))) ((eq type 'keyword) (let ((org-inhibit-startup-visibility-stuff t) (org-startup-align-all-tables nil)) (if (boundp 'org-table-coordinate-overlays) (progn (mapc ... org-table-coordinate-overlays) (setq org-table-coordinate-overlays nil))) (let* ((--invisible-types ...) (--markers\? ...) (--data ...)) (unwind-protect (progn ...) (save-excursion ...)))) (message "Local setup has been refreshed")) ((eq type 'plain-list) (let* ((begin (org-element-property :contents-begin context)) (struct (org-element-property :structure context)) (old-struct (copy-tree struct)) (first-box (save-excursion ... ... ...)) (new-box (cond ... ... ... ...))) (cond (arg (let ... ...)) ((and first-box ...) (org-list-set-checkbox begin struct new-box))) (if (equal (org-list-write-struct struct ... old-struct) old-struct) (progn (message "Cannot update this checkbox"))) (org-update-checkbox-count-maybe))) ((memq type '(node-property property-drawer)) (call-interactively #'org-property-action)) ((eq type 'radio-target) (call-interactively #'org-update-radio-target-regexp)) ((eq type 'statistics-cookie) (call-interactively #'org-update-statistics-cookies)) ((memq type '(table-row table-cell table)) (if (eq (org-element-property :type context) 'table\.el) (message "%s" (substitute-command-keys "\\<org-mode-map>Use `\\[org-edit-special]' to edit t...")) (if (or (eq type ...) (and ... ...)) (save-excursion (if ... ... ... ... ...)) (org-table-maybe-eval-formula) (cond (arg ...) (...) (t ...))))) ((eq type 'timestamp) (funcall pcase-0)) ((eq type 'planning) (cond ((org-at-timestamp-p 'lax) (funcall pcase-0)) ((run-hook-with-args-until-success 'org-ctrl-c-ctrl-c-final-hook) nil) (t (user-error (substitute-command-keys "`\\[org-ctrl-c-ctrl-c]' can do nothing useful here"))))) ((null type) (cond ((org-at-heading-p) (call-interactively #'org-set-tags-command)) ((run-hook-with-args-until-success 'org-ctrl-c-ctrl-c-final-hook) (funcall pcase-1)) (t (funcall pcase-2)))) ((run-hook-with-args-until-success 'org-ctrl-c-ctrl-c-final-hook) (funcall pcase-1)) (t (funcall pcase-2)))))
  (cond ((or (and (boundp 'org-clock-overlays) org-clock-overlays) org-occur-highlights) (if (boundp 'org-clock-overlays) (progn (org-clock-remove-overlays))) (org-remove-occur-highlights) (message "Temporary highlights/overlays removed from current...")) ((and (local-variable-p 'org-finish-function) (fboundp org-finish-function)) (funcall org-finish-function)) ((org-babel-hash-at-point)) ((run-hook-with-args-until-success 'org-ctrl-c-ctrl-c-hook)) (t (let* ((context (org-element-lineage (org-element-context) '(babel-call clock dynamic-block footnote-definition footnote-reference inline-babel-call inline-src-block inlinetask item keyword node-property paragraph plain-list planning property-drawer radio-target src-block statistics-cookie table table-cell table-row timestamp) t)) (type (org-element-type context))) (if (eq type 'paragraph) (progn (let ((parent ...)) (if (and ... ...) (progn ... ...))))) (let* ((pcase-2 #'(lambda nil ...)) (pcase-1 #'(lambda nil)) (pcase-0 #'(lambda nil ...))) (cond ((memq type '...) (if org-babel-no-eval-on-ctrl-c-ctrl-c nil (org-babel-eval-wipe-error-buffer) (org-babel-execute-src-block current-prefix-arg ...))) ((org-match-line "[ \11]*$") (or (run-hook-with-args-until-success ...) (user-error ...))) ((memq type '...) (let (...) (if info ...))) ((eq type 'clock) (org-clock-update-time-maybe)) ((eq type 'dynamic-block) (save-excursion (goto-char ...) (org-update-dblock))) ((eq type 'footnote-definition) (goto-char (org-element-property :post-affiliated context)) (call-interactively 'org-footnote-action)) ((eq type 'footnote-reference) (call-interactively #'org-footnote-action)) ((memq type '...) (save-excursion (goto-char ...) (call-interactively ...))) ((eq type 'item) (let* (... ... ... ... ... ...) (org-list-set-checkbox ... struct ...) (org-list-struct-fix-ind struct parents 2) (org-list-struct-fix-item-end struct) (org-list-struct-fix-bul struct prevs) (org-list-struct-fix-ind struct parents) (let ... ... ...))) ((eq type 'keyword) (let (... ...) (if ... ...) (let* ... ...)) (message "Local setup has been refreshed")) ((eq type 'plain-list) (let* (... ... ... ... ...) (cond ... ...) (if ... ...) (org-update-checkbox-count-maybe))) ((memq type '...) (call-interactively #'org-property-action)) ((eq type 'radio-target) (call-interactively #'org-update-radio-target-regexp)) ((eq type 'statistics-cookie) (call-interactively #'org-update-statistics-cookies)) ((memq type '...) (if (eq ... ...) (message "%s" ...) (if ... ... ... ...))) ((eq type 'timestamp) (funcall pcase-0)) ((eq type 'planning) (cond (... ...) (... nil) (t ...))) ((null type) (cond (... ...) (... ...) (t ...))) ((run-hook-with-args-until-success 'org-ctrl-c-ctrl-c-final-hook) (funcall pcase-1)) (t (funcall pcase-2)))))))
  org-ctrl-c-ctrl-c(nil)
  funcall-interactively(org-ctrl-c-ctrl-c nil)
  call-interactively(org-ctrl-c-ctrl-c nil nil)
  command-execute(org-ctrl-c-ctrl-c)

I use 2-factor authentication and hence I have created an app password for mu4e. My ~/.authinfo.gpg for Gmail looks as follows:

machine imap.gmail.com login kaletejas2006@gmail.com password <app password> port 993
machine smtp.gmail.com login kaletejas2006@gmail.com password <app password> port 587

My mu4e configuration relevant to Gmail is as follows:

(use-package mu4e
  :load-path "/usr/local/share/emacs/site-lisp/mu/mu4e"
  :config
  (setq mu4e-maildir "~/Maildir")
  ;; in my gmail account, any message marked for deletion will go to trash.
  (setq mu4e-contexts
        `( ,(make-mu4e-context
             :name "Gmail"
             :match-func (lambda (msg) (when msg
                                    (string-prefix-p "/Gmail" (mu4e-message-field msg :maildir))))
             :vars '(
                                        ;(mu4e-maildir . "~/maildir/gmail")
                     (mu4e-sent-folder . "/Gmail/[Gmail].Sent Mail")
                     (mu4e-drafts-folder . "/Gmail/[Gmail].Drafts")
                     (mu4e-trash-folder . "/Gmail/[Gmail].Trash")
                     (mu4e-refile-folder . "/Gmail/[Gmail].Archive")))
           ))

  ;; allow for updating mail using 'u' in the main view:
  (setq mu4e-get-mail-command "offlineimap")

  (require 'smtpmail)

  ;; now i set a list of
  (defvar my-mu4e-account-alist
    '(("Gmail"
       (mu4e-sent-folder "/Gmail/[Gmail].Sent Mail")
       (user-mail-address "kaletejas2006@gmail.com")
       (smtpmail-smtp-user "Tejas Kale")
       (smtpmail-local-domain "gmail.com")
       (smtpmail-default-smtp-server "smtp.gmail.com")
       (smtpmail-smtp-server "smtp.gmail.com")
       (smtpmail-smtp-service 587)
       )
      ))

  (defun my-mu4e-set-account ()
    "set the account for composing a message.
    this function is taken from:
        https://www.djcbsoftware.nl/code/mu/mu4e/multiple-accounts.html"
    (let* ((account
            (if mu4e-compose-parent-message
                (let ((maildir (mu4e-message-field mu4e-compose-parent-message :maildir)))
                  (string-match "/\\(.*?\\)/" maildir)
                  (match-string 1 maildir))
              (completing-read (format "Compose with account: (%s) "
                                       (mapconcat #'(lambda (var) (car var))
                                                  my-mu4e-account-alist "/"))
                               (mapcar #'(lambda (var) (car var)) my-mu4e-account-alist)
                               nil t nil nil (caar my-mu4e-account-alist))))
           (account-vars (cdr (assoc account my-mu4e-account-alist))))
      (if account-vars
          (mapc #'(lambda (var)
                    (set (car var) (cadr var)))
                account-vars)
        (error "No email account found"))))
  (add-hook 'mu4e-compose-pre-hook 'my-mu4e-set-account)

  ;; save attachments to downloads
  (setq mu4e-attachment-dir "/Users/tejas/Downloads/")

  ;; don't keep message buffers around.
  (setq message-kill-buffer-on-exit t)

  ;; use helm to select mailboxes.
  (setq mu4e-completing-read-function 'completing-read)

  ;; do not ask for context everytime mu4e is opened.
  (setq mu4e-context-policy 'pick-first)

  ;; do not ask when quitting.
  (setq mu4e-confirm-quit nil))

Any idea what I'm doing wrong? Thanks...

  • 1
    (setq smtpmail-debug-info t), retry, and look for a buffer whose name starts with '*trace of SMTP session'. That buffer will contain the actual SMTP commands that are being sent, it might indicate where the problem lies. – rpluim Mar 28 at 11:48
  • @rpluim Thanks for your response. I have pasted the trace here. Any idea what's wrong? – tejas_kale Mar 28 at 17:55
  • Hmm, maybe you need to specify your username in authinfo.gpg without the '@gmail.com' bit? That's what I have locally – rpluim Mar 29 at 13:55
  • That did not help. It gave the same error trace. – tejas_kale Mar 29 at 15:09
  • Hmm, (setq auth-source-debug t) will have auth-source log stuff to 'Messages', maybe the wrong thing is being looked up. – rpluim Mar 29 at 17:32
1

I had set the variable smtpmail-smtp-user to my name instead of my email ID. Correcting it got rid of the error. Thanks to @rpluim for helping me debug the issue.

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