Questions tagged [smtp]

Simple Mail Transfer Protocol (SMTP) is an Internet standard for electronic mail (email) transmission.

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How to fix: Mail - Can't connect to the account "iCloud". Enter the password for user ""?

Note that I am aware of this question: Getting bizarre error message from Mail But, the single answer doesn't really provide enough info to fix the problem. ===== This on an M1 MBA running 13.5.2 ...
Buadhai's user avatar
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How to generate a persistent TLS Fingerprint for the msmtp SMTP client

I am using msmtp as a mail client on an M1 iMac still running Monterey. I use Gmail as a relay. It's been working fine, except recently I started getting the following error message: send-mail: TLS ...
Buadhai's user avatar
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macOS Server: How to make mail server use TLS/SSL

I've set up the Mail component in the Server.app to provide an internal mail server. We used to use this mail server to send mail (via SMTP) without TLS on port 25 which worked well enough. Now I ...
not2savvy's user avatar
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How to deal with two mail binaries?

I recently installed both msmtp (smtp client) and mailutils on an M1 iMac via MacPorts. I couldn't get msmtp to work until I realized that there were two mail binaries on the machine, one that, I ...
Buadhai's user avatar
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Which plist contains macOS Mail SMTP server list?

Question about macOS Mail, under Monterey: I want to backup the list of outgoing servers, which has some obscure problems. After an extensive search (at least it seemed extensive), I can't find the ...
emendelson's user avatar
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Can PHPMailer send emails without configuring MacOS mail client on Monterey?

On a brand new Macbook running Monterey (M1), as PHP was removed by Apple on OS 12, I have removed all "AMP" preinstalled by Apple and installed HomeBrew "AMP" (with PHP 7.4), ...
Riccardo's user avatar
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Mail SMTP server list discrepancy

When I'm in Accounts and I select the dropdown of SMTP servers I get a long list of servers (as I manage a lot of accounts). But when I go to edit the SMTP server list, not all of the accounts in the ...
Rusty's user avatar
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Added new account to Apple Mail, it can't authenticate though webmail works fine

I'm out of ideas on what to try here. 2018 MBP running Mojave 10.14.6. I just received a new work email address, that was just created and has never been used before. I have numerous other email ...
JVC's user avatar
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macOS Mail won't clear out the outgoing SMTP server list

macOS Mail won't clear out the outgoing SMTP server list PLEASE NOTE three symptoms in one that makes this extremely buggy: going to "Edit SMTP server list..." and then deleting the items ...
Jason FB's user avatar
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Mail can't connect to Gmail SMTP server

I recently updated my Mac Pro from Sierra to High Sierra and now Mail cannot connect to the Gmail SMTP server. So I can receive mail but I cannot send. I have found posts from many other users with ...
sbarrettmusic's user avatar
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How to get postfix send mail (with Gmail smtp) under macOS Catalina?

I have tried everything (I guess), such as writing my sasl_passwd and editing main.cf in the /etc/postfix folder (as described in 1). I also copied my LaunchDaemon plist with a different name to my /...
pilgix's user avatar
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Mail.app keeps changing my SMTP settings?

I've setup my email account with Mail.app. However, I cannot send mail. The reason for this is that whenever I try to send mail, Mail.app always selects a legacy SMTP server, which I used to have ...
wen's user avatar
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Able to receive but unable to send emails on macOS Mojave from any account using any app

I have a 2018 15" MacBook Pro running macOS Mojave 10.14.2. I am unable to send emails from any account (be it Yahoo, Hotmail, AOL or others) using any app (tried the default Mail app, Canary Mail, ...
yssup's user avatar
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What macOS mail applications support a "Send Only" email account?

I'd like to revisit a question which has come up before (more on that below), but which does not, in my opinion, have a good “future-proof” solution looking forward to 2019 and beyond. “Send Only” ...
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How do I eliminate SMTP servers in the settings that I no longer use?

Earlier today, I asked a question about SMTP server settings on my iPhone (iOS 11.2.5). I've more or less figured that one out. I realize that it doesn't really matter, but how do I get rid of all ...
Ben Miller's user avatar
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How do I select a new SMTP "Primary Server"?

On my iPhone (iOS 11.2.5), I had to change the SMTP server for my e-mail account. I was able to add the new SMTP server, which appeared under "OTHER SMTP SERVERS". I was also able to turn off the ...
Ben Miller's user avatar
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Accessing Gmail From Terminal

Is there a way to access my Gmail smtp account just using the terminal or is this not possible? I saw this link but it did not help: https://medium.com/@stessyco/gmail-from-the-command-line-with-...
Cody Rutscher's user avatar
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iOS Mail Turns off SMTP Server if two or more are listed

iPad iOS version 11.2 (latest update). Two different email accounts on this device. We use third party SMTP providers (mailgun/sendgrid) for email deliverability/trackability stats. Each address ...
gigaboy's user avatar
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11 votes
9 answers
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Why do I get a 'connection to the outgoing server "smtp.gmail.com" failed' message in iOS Mail?

Today I noticed I have 3 emails stuck in my Outbox, and when I try to re-send one, I see: If I press Settings, then select "SMTP Gmail SMTP Server", and "Gmail SMTP Server" (under PRIMARY SERVER--it ...
Daryl Spitzer's user avatar
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2 answers
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Why is my mac replacing my name on all my email as "Holiday In The United States"?

Recently I noticed that on both Spark and the default mail app, my name is being replaced as "Holiday In The United States". This is happening on all my accounts, with various email providers. I have ...
Rushil Srivastava's user avatar
1 vote
2 answers
4k views

Apple Mail: Only TLS v1.0 supported on macOS 10.11

I'm on OS X 10.11.3, aka El Capitan. I can't connect to mail servers running only TLS version 1.2 or 1.1 with Apple Mail. IMAP as well as SMTP connections are always established using TLS 1.0. ...
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I cannot send GMAIL using Outlook 2016

I have Outlook 2016 and I'm trying to pickup my gmail using IMAP. I can receive emails, but it does not send when doing a test send on setting up the email. Error code: 0x800cce05 SMTP Server: smtp....
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4 answers
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El Capitan Outgoing Mail server problems

Just upgraded to El Capitan on my Mac mini. Mail has a problem though I have multiple mail accounts set-up The outgoing SMTP smtp server for all accounts is NONE If I assign one from the drop list ...
Mike W's user avatar
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How can I use smtp to connect email to mail client

Right so we have set up a mail server for our company that does not use imap nor pop at the moment, it is based on smtp port 25 and I can't figure out how to link it with my mail client as it always ...
Ilja's user avatar
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2 answers
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Can't send or receive e-mail via Mail

I've tried multiple e-mail accounts and can't get my computer to talk to the e-mail server. I've loaded and re-loaded the SMTP and IMAP settings. Everything seems in order, but it just doesn't want ...
Kweder's user avatar
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4 votes
2 answers
7k views

Mail Immediately forgets SMTP Password

I'm trying to set up Apple Mail to send through my web host's SMTP server (not Gmail, or any common email provider), and as soon as I save the SMTP settings, Mail forgets the password, meaning that ...
Joshua Dwire's user avatar
2 votes
1 answer
134 views

Mail: Select SMTP server automatically on addressee

I have two SMTP servers configured in Mail. One for school, and one for my private email. I would like that Mail automatically picks the one for school if I'm sending an email to someone of my school. ...
Martijn Courteaux's user avatar
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1 answer
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Simple telnet session fails on OS X

I am learning Postfix and how it works with SMTP, and here's a sample session that the book shows as an example: I ran the command hostname on my Mac terminal, and it showed <some_id>.ant....
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1 answer
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OS X SMTP issue - Unable to send email (gmail)

I have installed OS Yosemite 10.10.1 a couple of months ago. Everything was ok especially with mail. However a couple of days ago it just stopped to sending emails with no apparent reason since none ...
Paul's user avatar
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1 vote
2 answers
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Use only SMTP server without a mailbox

In Mail.app I have several mail addresses and incoming mail to some addresses is already being forwarded to my primary mail address. I don't want to have an inbox for these secondary emails (I've got ...
Can Poyrazoğlu's user avatar
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1 answer
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Adding POP3/SMTP to iPod 8.1

My daughter was using my old iPod Version 6.1.3/Model MC54LL/A, and Santa just brought her her own iPod Version 8.1/ModelPD717LL/A. I had her email going to my old iPod. It is going through my own ...
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Creating an account and sending mail using applescript

I'm trying to use applescript to do two things: Create an account in Mail.app Using that account, send an email in Mail.app I'm having an issue with creating an account on Mail.app mainly because ...
erictsai626's user avatar
1 vote
0 answers
883 views

STARTTLS handshake against Apple smtp server fails

Recently, my email setup using Emacs/24.4 + Gnus/5.13 on OX Yosemite stopped working against the Apple smtp server: smtp.mail.me.com. It has been working fine for years before. It seems that it ...
The Dude's user avatar
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1 vote
1 answer
286 views

Does default e-mail port behave differently than custom?

I'm trying to setup mail on Mavericks to talk directly to my mail server at an ISP. I use the ISP for my mail, but filter it through Gmail and that works. So, here's what I've tried: telnet to port ...
Mark's user avatar
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0 answers
495 views

Apple Mail is mixing up table entry and mail view (header and body information)

I have an oldish computer that is running Aplle's Mail program with a large amount of mail coming in (the current number of emails on the computer is in the tens of thousands). Recently it has started ...
lindon fox's user avatar
3 votes
1 answer
908 views

How Can I Trace the Origin of Outbound Spam Mail in Mavericks Server?

My Mavericks Server mail server has been compromised and has been sending reams of Nigerian royalty scam emails out. Where can I find log files which will enable me to track down the IP address these ...
Waragainstsleep's user avatar
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627 views

mail app not sending appropriate Reply To addresses from different email accounts

My wife has a MacBook Pro (10.8.2) with a Telus home internet connection. She uses the Mac mail app (6.2) and her primary email account is a Gmail address, which she has been using with no problem (...
mycroft's user avatar
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1 vote
0 answers
57 views

How can I send an email from within iCloud.com using a different email address? [duplicate]

I have my own private domain hosting solution with email, for example, [email protected]. When I am using the iCloud.com website from my browser, let's say for creating a spreadsheet, I will want to shed ...
Bartley's user avatar
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3 votes
1 answer
5k views

How to enable Mac OS X server email alerts

I have a specific Mac mini server that does not send out email alerts, even though I have an email address configured. I also want to note that I am not using the mail server within server.app. I ...
David Killingsworth's user avatar
1 vote
2 answers
2k views

How do I start a fake SMTP server automatically?

I'm using Mac 10.9.1. I would like to install a fake SMTP server on my system -- one that listens for emails on port 25 but doesn't actually do anything with them. I'd like this process to start ...
Dave's user avatar
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12 votes
5 answers
76k views

How to setup Gmail SMTP server for OSX Mail with 2-step-verification and App-specific password?

Haven't been able to solve this problem with the threads such as here. My Gmail stops always working after a while, perhaps after accessing it in different WIFI network or something like this -- it is ...
hhh's user avatar
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9 votes
3 answers
9k views

Why is OS X able to send out email without first configuring SMTP?

When I try the command in terminal, an email is sent. I have checked there is no local SMTP is running, so what is the mechanism used by Apple behind the scene? echo "Hello" | mail -s "Test" foo@bar....
Yoga's user avatar
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1 answer
211 views

Cannot get postfix to listen on wifi interface (en1)

I have a Mac running 10.8.4 which I am using as a server which is only connected to my network via Wifi (en1), however I cannot get the stock postfix process to listen on en1. I have tried a variety ...
trojanfoe's user avatar
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2 votes
2 answers
3k views

macbook air mail: how to configure HELO sent to smtp server?

Hello I am trying to set up a mail account on a new macbook air (Lion 10.7.5 Build 11G63B). I have gone through all the steps but it will not connect to the smtp server. I am using straight SMTP (not ...
starfry's user avatar
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2 votes
1 answer
5k views

Mail won't let me turn off SSL for SMTP

I just upgraded from Lion to Mountain Lion. I have eight email accounts set up in Mail.app. Some of my SMTP servers support SSL and some don't. But now Mail.app turned SSL on for every server (except ...
SSteve's user avatar
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11 votes
4 answers
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How to set reply-to address in Apple Mail

I have two accounts set up in Apple Mail. The second account is for backup purposes and because at times the primary account is unavailable. When that happens, I send from the second account but would ...
Mark's user avatar
  • 221
5 votes
1 answer
6k views

SMTP Issues with Mountain Lion 10.8

BACKGROUND I upgraded from 10.7 to 10.8 on 7/28/12 I upgraded Xcode from 4.4 to 4.4.1 on 8/8/12 PROBLEM On 8/9/12, on my MacBook Air, Mail.app refuses to connect to the SMTP service on a server ...
Mike Loiterman's user avatar
3 votes
1 answer
1k views

What is a neat way to delete a stale amavisd pid_file on first boot after panic or power failure?

Lion Mail Server component postfix/smtp 100% reproducible blocks inbound smtp mail delivery on first boot after a panic or power failure. Error messages from mail.log are like: postfix/smtp[45785]: ...
Pro Backup's user avatar
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How can I send smtp mail via gmail and osx Lion mailx?

I would like to be able to send email from utility/batch/launchd scripts via my gmail account and the mailx client that is bundled in OS X Lion. I cannot find how to configure this. I found http://www....
djb's user avatar
  • 443
9 votes
5 answers
12k views

Gmail SMTP server going offline

I have a Google Apps account, with 2-step verification, set up in Apple mail. Typically it works great for several weeks, or a month, but then the SMTP server has (Offline) next to it, and it will ...
bassplayer7's user avatar
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