XAMPP Sendmail using Gmail account

Question

I'm trying to configure Sendmail through XAMPP to send email. In my sendmail.ini I have these settings:

# Set default values for all following accounts.

logfile "C:\xampp\sendmail\sendmail.log
account Gmail
tls on
port 587
tls_certcheck off
host smtp.gmail.com
from [e-mail]
auth on
user [e-mail]
password mypassword

account default : Gmail

I've created a test script like this:

$to = "[e-mail]";
$subject = "Hi!";
$body = "Hi,\n\nHow are you?";
$headers = "From: [e-mail]" . "\r\n";
if (mail($to, $subject, $body, $headers)) {
    echo ("Message successfully sent!");
} else {
    echo ("Message delivery failed...");
}

I get a message to say that the email was sent but it never arrives and in the logs I get:

sendmail: Error during delivery: Must issue a STARTTLS command first.

Does anybody know what the issue could be here?

Thanks in advance!

Gaz

Answer 1

Just to add to the already great responses. Make sure you are running XAMPP as Administrator. That was what fixed it for me.

Answer 2

There is another issue when using Gmail. Gmail now has security so that you must generate an application specific password - you can't use the password you have for your normal Gmail access. I discovered this by trying the examples above and then noticing that in the sendmail folder an error log had been generated. In the error log I came across a message indicating this.

Answer 3

All I had to do was switch the "Allow less secure apps to access your account" to on. I guess this is an alternative to creating an app specific password.

https://support.google.com/accounts/answer/6010255 for info

https://www.google.com/settings/security/lesssecureapps for the switch

Might be worth switching it back off after you're done for security purposes.

Answer 4

These are the most recent Google SMTP server requirements:

1. Gmail SMTP server address: smtp.gmail.com
2. Gmail SMTP password: (Your Gmail password)
3. Gmail SMTP port (TLS): 587
4. Gmail SMTP port (SSL): 465
5. Gmail SMTP TLS/SSL required: Yes

Google SMTP Requirements

If you just use SSL it gets complicated with the required Captcha verification test so I just set my SSL to auto which will try TLS when SSL Fails.

Answer 5

I know this is an oldish post but just thought I would share the fact that the following worked for me.

I am currently using a WAMP server on Windows 7 ENT with Apache/2.4.9 (Win64) PHP/5.5.12, and MySQL 5.6.17.

I followed this tutorial: http://blog.techwheels.net/send-email-from-localhost-wamp-server-using-sendmail/

Answer 6

THIS IS WHAT YOU SENDMAIL SHOULD LOOK LIKE


[sendmail]

; you must change mail.mydomain.com to your smtp server,
; or to IIS's "pickup" directory.  (generally C:\Inetpub\mailroot\Pickup)
; emails delivered via IIS's pickup directory cause sendmail to
; run quicker, but you won't get error messages back to the calling
; application.

smtp_server=smtp.gmail.com

; smtp port (normally 25)

smtp_port=465

; SMTPS (SSL) support
;   auto = use SSL for port 465, otherwise try to use TLS
;   ssl = always use SSL
;   tls  = always use TLS
;   none = never try to use SSL

smtp_ssl=auto

; the default domain for this server will be read from the registry
; this will be appended to email addresses when one isn't provided
; if you want to override the value in the registry, uncomment and modify

;default_domain=mydomain.com

; log smtp errors to error.log (defaults to same directory as sendmail.exe)
; uncomment to enable logging

error_logfile=error.log

; create debug log as debug.log (defaults to same directory as sendmail.exe)
; uncomment to enable debugging

debug_logfile=debug.log

; if your smtp server requires authentication, modify the following two lines

auth_username=Your Email Here
auth_password=Your Password Here

; if your smtp server uses pop3 before smtp authentication, modify the 
; following three lines.  do not enable unless it is required.

pop3_server=
pop3_username=
pop3_password=

; force the sender to always be the following email address
; this will only affect the "MAIL FROM" command, it won't modify 
; the "From: " header of the message content

force_sender=Your Email Here

; force the sender to always be the following email address
; this will only affect the "RCTP TO" command, it won't modify 
; the "To: " header of the message content

force_recipient=

; sendmail will use your hostname and your default_domain in the ehlo/helo
; smtp greeting.  you can manually set the ehlo/helo name if required

hostname=smtp.gmail.com

THIS IS WHAT YOU PHP.INI FILE SHOULD LOOK LIKE

[mail function]
; XAMPP: Comment out this if you want to work with an SMTP Server like Mercury
smtp_server=smtp.gmail.com
smtp_port = 465

; For Win32 only.
; http://php.net/sendmail-from
;sendmail_from = postmaster@localhost

; XAMPP IMPORTANT NOTE (1): If XAMPP is installed in a base directory with spaces (e.g. c:\program filesC:\xampp) fakemail and mailtodisk do not work correctly.
; XAMPP IMPORTANT NOTE (2): In this case please copy the sendmail or mailtodisk folder in your root folder (e.g. C:\sendmail) and use this for sendmail_path.  
; XAMPP: Comment out this if you want to work with fakemail for forwarding to your mailbox (sendmail.exe in the sendmail folder)
sendmail_path = "\"C:\xampp\sendmail\sendmail.exe\" -t"

; XAMPP: Comment out this if you want to work with mailToDisk, It writes all mails in the C:\xampp\mailoutput folder
;sendmail_path = "C:\xampp\mailtodisk\mailtodisk.exe"

; Force the addition of the specified parameters to be passed as extra parameters
; to the sendmail binary. These parameters will always replace the value of
; the 5th parameter to mail(), even in safe mode.
;mail.force_extra_parameters =

; Add X-PHP-Originating-Script: that will include uid of the script followed by the filename
mail.add_x_header=Off