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I have been a happy Apple Mail via POP user for years. I have been using SpamSieve for a long time.

About a year ago I moved to using IMAP, so that my iPhone and MacBook Pro were aways in sync. Please could someone help me understand the "On My Mac" mail account? I see this below the list of Smart Mailboxes. It was my understanding that all mail from an IMAP account would remain on the mail server side. What is "On My Mac", and can I remove it? Thanks
On My Mac is the area where you would store anything that you wished to keep more or less permanently. If your ISP gives you lots of mailbox space, you may not care about this. My ISP gives me limited space per account, so I have rules set up to copy certain messages into folders that I have set up under On My Mac. If and when I delete some of them from the server, I still have local copies.

I also have mail stored from an account that no longer exists, from my former employer who went out of business.

I have local folders set up for my current business, for mail from friends and family, for transactions, for newsletters, etc.
 


Speaking of IMAP and local folders, I wanted to use MailMate, which is a really well-made IMAP-only mail program. But, for me, it has a single fatal flaw: its developer seems to be philosophically opposed to local folders. The program does not include them. What a shame!
 


About a year ago I moved to using IMAP, so that my iPhone and MacBook Pro were aways in sync. Please could someone help me understand the "On My Mac" mail account? I see this below the list of Smart Mailboxes. It was my understanding that all mail from an IMAP account would remain on the mail server side. What is "On My Mac", and can I remove it? Thanks
Any message still listed under your list of email account mailboxes (i.e. under the 'Mailboxes' heading) is only a copy of what is held on your provider's server. So you will see the same messages on your phone or whatever other device you view your email with.

If you move a message out of the in-box to a folder within "On My Mac", you are removing that item from the email provider's server. The only remaining copy of the message is the one stored on your Mac. The message will therefore disappear from any other device showing that account in-box.

I do this regularly to file my messages in folders on my Mac (where they are regularly backed up) to keep the content of my in-box to a minimum. It also ensures I have a complete, organised archive of all my email on backup.
 


Any message still listed under your list of email account mailboxes (i.e. under the 'Mailboxes' heading) is only a copy of what is held on your provider's server. So you will see the same messages on your phone or whatever other device you view your email with.
Thanks for the response. My question relates to behavior I am seeing where some messages land in the On My Mac inbox. I'm guessing that SpamSieve has something to do with that.

I really would love to know where On My Mac gets set up. Anyone?
 


If you move a message out of the in-box to a folder within "On My Mac", you are removing that item from the email provider's server. The only remaining copy of the message is the one stored on your Mac. The message will therefore disappear from any other device showing that account in-box.
To be clear, there is "move", which should remove the message from the server, and there is "copy", which should leave the message intact on the server. Both would make a local copy on your Mac. I mostly use the former to clear out messages on the server and archive them. I rarely use the latter.
 


More on junk mail (Mail 12.2, macOS 10.14.3):

Apple Mail's Junk Mail Filtering has worked pretty well for me in the past, but a few months ago I started getting lots of false positives, including many where the sender is in my contacts. Examples include daily calendar alerts from Google (sent to my Gmail address) and daily weather alerts from Meteoblue (send to my Dot Mac address). There are many others including Deb Specs, from whom I buy reading glasses and Sees Candies, from whom I order goodies for my aged step-mother.

In Mail preferences I have all three boxes under "The following types of messages are exempt…." checked. So, theoretically, if the sender is in my contacts, Mail should not flag it as junk. This doesn't seem to work.

I tried "training" Mail by marking all of the false positives as Not Junk, but that seemed to have no effect. I finally bit the bullet and did a "Reset" of Junk. That worked for a few days, but the false positives have started showing up again.

What does work is writing a separate rule for each false positive email address, but I shouldn't have to do that, should I?
 


Thanks for the response. My question relates to behavior I am seeing where some messages land in the On My Mac inbox. I'm guessing that SpamSieve has something to do with that.
Ah, yes - that's probably the case. I not familiar with SpamSieve , so I can't say for sure. But I see the same where I have set up rules in Mail to sort incoming email into local folders. When the rules run, any messages they process disappear from the server. But I only do this for messages that don't require urgent action, so it helps keep may inbox focussed on things I really need to read.
 


... Please could someone help me understand the "On My Mac" mail account?

... I really would love to know where On My Mac gets set up. Anyone?
It might help to think of On My Mac as "a place to put stuff" rather than as "an account". It doesn't need to be set up specifically the way an external account does. Rather, it's built in, and there all along if you want to use it.

If you're using SpamSieve with IMAP, it's definitely worth reading the SpamSieve manual sections on "SpamSieve and Multiple Macs", "iPhone Spam Filtering", and related topics. It'll help explain what you're seeing, and give some great (if sometimes slightly complicated) suggestions about how to make this all work really well.
 


I'm seeing a problem in macOS Sierra Mail where attachments in my POP account often do not show in the Attachments column, the Remove Attachments menu item is dimmed, but the attachment info does show up in the popup toolbar thing between the header and message body, and they do show up in the message. It's inconsistent. I am not sure when this started happening. Doesn't seem to happen on my Exchange account.
I'm also running Sierra. I just checked two messages, each with an attachment. I have a couple of different ISPs, one is IMAP and one is POP. I found one (among several with attachments) POP message where the "Remove Attachment" entry is grayed out; for the IMAP account, none are. Not sure why that is though. and I haven't checked all messages with attachments.
 


Regarding Remove Attachments entry being greyed out: is it possible you're in Conversation view, and have selected a reply instead of the original message containing the attachment? In case it helps: there is a blue selection box showing which message is selected in a conversation.
 


I have had this problem even with older versions of the OS. Someone suggested long ago that this can be fixed by adding the following "Rule" in Mail Preferences:

If all of the following conditions are met
Any attachment name contains .
<==(Note: the name contains a period)
Perform the following actions:
Mark as Read
Well I'll be, that did the trick! Thanks for the tip, Jim.
 


Please could someone help me understand the "On My Mac" mail account? I see this below the list of Smart Mailboxes. It was my understanding that all mail from an IMAP account would remain on the mail server side. What is "On My Mac", and can I remove it? Thanks
"On My Mac" is a "mailbox," not an "account." It is nothing more than a place on your Mac where you can put email messages and read them with the Apple Mail app. Lose your Mac or its drive, and you have lost the messages in the "On Your Mac" mailbox. If it contains important messages, you need to protect it in the same way you would protect any important files on your Mac.

In fact, the "On My Mac" mailbox is not necessarily even associated with an email account -- it can hold email messages from email accounts that don't even exist any more, and it can hold messages that originated from multiple different accounts. You can think of an "On My Mac" mailbox as a folder on your Mac that contains Mail documents that the Mail app knows about, kind of like how the iTunes Music folder is just a folder filled with files that iTunes knows about.

It is very important to remember that if you move an email message to an "On My Mac" mailbox, then that message exists only on your Mac. If it is an important message, be sure to have a reliable backup of it somewhere else.
 


It is very important to remember that if you move an email message to an "On My Mac" mailbox, then that message exists only on your Mac. If it is an important message, be sure to have a reliable backup of it somewhere else.
Unless, of course, your mail service provider archives all messages, even if you delete them. Many corporations and the US government do that, because of legal requirements.
 




... I really would love to know where On My Mac gets set up. Anyone?
On My Mac is the place where local storage mailboxes reside that are not part of any account. They appear in their own section, On My Mac ,in the Mailboxes sidebar (called "Mailbox List" in the Mail > View menu).

To create a new On My Mac mailbox, use Mail > Mailboxes > New Mailbox... and set Location: to On My Mac. Messages are either copied/moved into these mailboxes manually or by rule, never directly synchronized with or downloaded from a server. Of course, this means that messages in On My Mac mailboxes are only available on the local macOS user account. Otherwise, they have the same foibles as any other mailbox in Apple Mail.

My go-to reference is "Take Control of Apple Mail, Fourth Edition" by Joe Kissell.
 


FWIW, I also have been seeing blank contents in some mails at times, but I have not taken the time to diagnose what's happening.
I’m using macOS 10.14.3 on a late 2013 13” Retina MacBook Pro. Since updating to Mojave, I, to,o have experienced the blank email messages in the "Classic" layout mode. No observable pattern for when it happens, sometimes once a day or not for several days. My solution is to go to a previously read email, which displays correctly, then click back on the "blank" email, and its contents always appears.
 


KJM

If she clicks on a link in an email (usually a Pinterest mailing but others, too), Safari comes to the front, and a Yahoo search page appears (her default search engine is DuckDuckGo).…
I tried deleting the com.apple.mail.plist file in Preferences, but I don't think that is being used anymore, since it didn't create a new one when I re-launched Mail.app.

So, any ideas why it's the Yahoo search page that opens? Besides trashing preferences, is there anything else I can try?
What makes you think deleting Mail's preferences would change Safari's behavior? I think your Mom' Mac has caught some Mal- or Adware infection — perhaps by clicking some bad links.…

So I'd recommend using e.g. the free Malwarebytes app or DetectX Swift to search for and remove any unwanted software from her Mac. Then hopefully her Safari will act normally again.
 


Unless, of course, your mail service provider archives all messages, even if you delete them. Many corporations and the US government do that, because of legal requirements.
Don't automatically assume that the cloud mail service you or your company uses actually backs up your e-mail. My employer migrated us all over to Office365. Some months after the migration was done somebody discovered that a mail folder with several archived old e-mails wasn't accessible... it appeared to be corrupt. When IT asked Microsoft to restore the folder from their backups, Microsoft said "what backups?"

Sure enough, they don't back up your e-mail. Sure, they make redundant copies of what's in your account, in case one of their data centers explodes, but if some portion of that is corrupt, then they have redundant copies of corrupted e-mail. I tell all of my users that if they have e-mail they absolutely do not want to lose, put it in a local mail folder. Since we back up all end-user computers, that's the only way I can try to ensure their mail won't disappear.

And, FWIW, the lawyers here don't want e-mail kept more than 30 days... for legal reasons.
 



Unless, of course, your mail service provider archives all messages, even if you delete them. Many corporations and the US government do that, because of legal requirements.
You're not wrong, but permanently or indefinitely archiving emails is considered to be a poor compliance practice, unless the emails have been flagged for a litigation hold or otherwise contain extremely important information.

In fact, for liability and compliance reasons, most professionally managed email retention policies are written in terms of when data must be destroyed, not how long it must be preserved.

In any case, there's an enormous range of email retention policies out there, and implementing them reliably and consistently can be surprisingly challenging. Definitely do not rely on a retention policy alone to protect you.
 


When IT asked Microsoft to restore the folder from their backups, Microsoft said "what backups?"
That's an important point, often missed, when companies migrate from in-house mail systems to business versions of Microsoft Office 365 or Google G Suite.

While I think Microsoft and Google can do a better job of emphasizing the point, both do indicate that true backup and restore capabilities are not included in their services. Customers who want those services should invest in a proper backup solution, and there are a bunch of cloud-based third parties that specialize in backing up and restoring the business versions of Office 365 and G Suite.
 


What makes you think deleting Mail's preferences would change Safari's behavior? I think your Mom' Mac has caught some Mal- or Adware infection — perhaps by clicking some bad links.…

So I'd recommend using e.g. the free Malwarebytes app or DetectX Swift to search for and remove any unwanted software from her Mac. Then hopefully her Safari will act normally again.
Good thought but I ran Malwarebytes and nothing showed up. Besides, the behavior seems too uninteresting (opens a Yahoo search window) and too intermittent (only opens said window the first time the link is clicked but not the second, third, and so forth).
 


I've been having this same issue for the last couple of days. Apple Mail refused to send anything via iCloud using my **@mac.com on the first try. Subsequent tries usually succeeded without making any changes. In each case, the error message on the drop-down sheet said Apple didn't recognize my email address - the same email address I've had since iTools' first day.

But the issue seems to be getting worse over time. I tried several times earlier today, and it absolutely wouldn't send even on the second or third attempt. Finally I changed my "send from" to **@icloud.com, and it took it. But then another email right after, using the @icloud.com address, wouldn't go, with the drop-down sheet complaining.

Yet I'd cc'd myself on that email, and it came though just fine. So I'd say something is very wrong at Apple itself and has nothing to do with Apple Mail, my accounts or preferences. Apple says it's just fine and dandy, but it obviously isn't.
I have seen similar issues and fixed them by looking in keychain. There have been old entrys for me, iCloud, Mac, that for some reason mail behind the scenes decides to use.

Also look at the advanced outgoing settings in mail for the Apple account that there isn’t an old entry in there also. The quickest way I have found is to log out of my Apple ID, so it isn’t in mail at all. Then go delete all the iCloud, me, Mac entries in my keychain.

OS X Mail seems to be synchronizing preferences to a database in the system that then gets synced to the keychain. And I have seen a delay of this stuff getting updated.
 


Mom's iMac (macOS 10.13.6) has been having an unusual issue I can't seem to solve. It involves how links in Mail.app open in Safari. If she clicks on a link in an email (usually a Pinterest mailing but others, too), Safari comes to the front, and a Yahoo search page appears (her default search engine is DuckDuckGo). If she goes back to the email and clicks the link again, the correct Pinterest page appears. This is always the case: first click -> Yahoo, second and subsequent clicks -> actual link. If she right-clicks and chooses "open link", she never gets the Yahoo page. Change the default browser to Chrome, and the first click now goes to the correct page in Chrome. If she forwards me the Pinterest email, all the links open as they should in Safari.

I tried deleting the com.apple.mail.plist file in Preferences, but I don't think that is being used anymore, since it didn't create a new one when I re-launched Mail.app. Is the PersistenceInfo.plist file in the Preferences/Mail folder now the general preferences file for Mail? I didn't have time to test trashing that this afternoon.

So, any ideas why it's the Yahoo search page that opens? Besides trashing preferences, is there anything else I can try?
One thing you can do Is check the DNS entries under Apple, system prefs, network, and that network interface (such as the advanced settings under WiFi or Ethernet).

Also, if you look at the exact link in mail, before you click it, is that a direct Pinterest link or another website? Recently a client's website was going to a fake drug website any time someone clicked on it from Google, but not typing in the website name directly. Turns out there was malware in the client's website that was redirecting to the drug website if it was coming from a search engine but not directly.

Another client had a problem with an advertisement on an American Express website causing weird redirects and pop-ups when they would try and log into their account.

As a test, you could disable JavaScript in Safari temporarily then click the link in mail and see what is does.
 




IRS audit does not directly figure in email retention. The legal logic is this: as long as one has a retention policy and follows it (rather than discarding data only when a subpoena is expected), then all is well. Tax authorities require good records but do not specify email as a requirement. (I save tax information from both email and snail mail as PDF files right alongside ledger and other data files.) Leastways, that's what my daddy the attorney taught me.
 


Jim Meiss said:
I have had this problem even with older versions of the OS. Someone suggested long ago that this can be fixed by adding the following "Rule" in Mail Preferences:
If all of the following conditions are met
Any attachment name contains . <==(Note: the name contains a period)
Perform the following actions:
Mark as Read
Well I'll be, that did the trick! Thanks for the tip, Jim.
Darn, that seemed to work for a while, but now it only works with some attachments.

Mail.app does not always note the attachment in the "attachment" column. When it does, I can delete it; when it doesn't, I cannot. Some photos and some audio files show up in the "attachments", and others don't. I do not see a logical pattern. This is in Sierra, 10.12.6; Mail.app 10.3.
 


Mail.app does not always note the attachment in the "attachment" column. When it does, I can delete it; when it doesn't, I cannot. Some photos and some audio files show up in the "attachments", and others don't. I do not see a logical pattern. This is in Sierra, 10.12.6; Mail.app 10.3.
I found a workaround for what appears to be yet another non-fixable Apple bug:
  1. Select the email that has a non-removable attachment.
  2. Click on the "Redirect" button.
  3. Remove the attachments you don't want saved and then send this email to yourself.
  4. You may also want to first delete the original email before checking for new mail, or at least move it out of the Inbox, as Apple Mail may get confused when the redirected email comes in with the same subject and date stamp.
If you have hundreds of emails, this could be a real pain. But for a few, and if you keep up with new emails, it should be fine.
 


I found a workaround for what appears to be yet another non-fixable Apple bug:
  1. ...Click on the "Redirect" button
  2. ...
Another, similar workaround is to drag the message to the desktop. You can edit it with a text editor (if you are careful) to remove the attachment. Then you can re-import the message into Mail (just double-click on the message, then move it to a mailbox). Again, painful if you have many messages, but this one at least preserves the sender/received info.
 


... Additionally, Apple Mail will eventually just choke itself out once mailboxes reach high message counts (10K+)....
I have used Apple Mail since I had to abandon Eudora around 2008 or so. Currently, I have 11 email addresses (all, at this point, IMAP). My Inbox aggregate has over 18.5k emails, the Sent Mailbox has over 12k; there are 65 folders (and more subfolders) On My Mac, one of which has 8.5k emails.

I am using a maxed-out 15" MacBook Pro Retina (maxed-out, but 2012 vintage), and have not witnessed choking. Apple Mail is very responsive, and the search function works fine among all the mailboxes.

I will admit that the Gmail part of that Inbox aggregation (1 account) is almost never used – it has 144 emails, going back to January 2013. And I'll also add that Gmail has occasionally given me problems with authentication in Mail – so I can understand if Mr. Goldman's reference above is to sizable Gmail mailboxes.
 


A very strange problem here. Over the past few years for my AOL account, I've been sending spam emails as attachments to spam@aol.com. No problem there.

However, when updating to Mojave 10.14.4, I've been getting alerts that my email has an error. It is:
The server response was: Line length exceeded. See RFC 2821 #4.5.3.1.
The settings have been the same since I installed Mojave 10.14. I even deleted my AOL account in Apple Mail and re-entered the AOL account. Still the problem is the same.

How can I rectify the error? I'm perplexed. Thank you.
 


I'm curious why there is this persistent idea that Mail.app can not handle large quantities of email messages. I currently sync all messages for all my accounts, because I want a copy on my computer as well as in the cloud. I have 5 accounts, a Gmail account that is 11 years old, and a personal domain email account that is almost 20 years old. I use all of these email accounts on every one of my devices: iPhone, iPad, MacBook Pro 15, 2018 Mac Mini. The iPhone and iPad sync all emails as well. All devices are running the most current version of IOS and macOS.

All quantities are based on Mail.app "About this account" details:
  • Gmail account currently syncing via Gmail's IMAP implementation: 191,823 emails
  • personal domain email on G Suite account: 30,385 emails
  • Four other email addresses have less than 1000 emails.
I have a personal philosophy that is summed up simply as this: Lazy is Best. I acknowledge that I am terrible at organizing my email. I take full advantage of the fact that both Google and Apple are good at indexing and searching. Rather than stress out about it, I accepted my faults and just said "let it grow". I honestly can't remember the last time I had a problem with Mail.app that wasn't a self-inflicted problem.

I buy and sell computers all the time, so I'm backing up and restoring at least once a year. I typically upgrade my iPhone every year and my iPad every 2 years and have never had an email problem with the built in iOS mail app. My business as an IT consultant encounters clients with Apple products frequently, and I don't recall the last time I helped a customer with an email issue that was related to the quantity of email. In fact, I have encouraged many customers to stop using their cable company ISP email because of a ridiculous email limit that the customer was constantly having to accommodate. The relief they felt when switching to a Gmail account so they didn't have to worry about having to delete emails all the time was a job well done.

I certainly understand those who can't stand the thought of an unorganized email account; I'm married to one. My wife diligently empties her personal inbox on a daily basis. I also know why. She has worked in corporate America for 14 years, and Microsoft Outlook is notorious for limited inbox size and frequent issues when Outlook has too many emails.

In my experience, Mail.app is stable using standard IMAP accounts, Google IMAP accounts, and iCloud accounts. It has no problem managing 100K emails, and search in email works well and as expected. While I never discount individual problems, in aggregate, I think most email users are well served by Apple's apps.
 


I have used Apple Mail since I had to abandon Eudora around 2008 or so. Currently, I have 11 email addresses (all, at this point, IMAP). My Inbox aggregate has over 18.5k emails, the Sent Mailbox has over 12k; there are 65 folders (and more subfolders) On My Mac, one of which has 8.5k emails.
Yeah, these days Mail doesn't choke — if it ever did, certainly not for me. I have two accounts (one IMAP, one Exchange), over 27K messages in the Inbox, and well over double that number in total with messages going back to 2006. No performance problems at all.

No Gmail though...
 


I'm curious why there is this persistent idea that Mail.app can not handle large quantities of email messages. I currently sync all messages for all my accounts, because I want a copy on my computer as well as in the cloud. I have 5 accounts, a Gmail account that is 11 years old, and a personal domain email account that is almost 20 years old. I use all of these email accounts on every one of my devices: iPhone, iPad, MacBook Pro 15, 2018 Mac Mini. The iPhone and iPad sync all emails as well. All devices are running the most current version of IOS and macOS.
Speaking for myself, but echoing what I have heard from some others, we speak from experience. Since I switched from Eudora several years ago, after it became unreliable, Apple Mail has repeatedly shown signs of instability after the number of files it contains exceeds several thousand emails. Moving them out of the Inbox into separate folders "On my Mac" avoids the problem.

I see two particular problems with Apple Mail as the Inbox grows full. The most frequent is extreme slowness in response both to my typing on screen in Mail and to sorting the mail - for example, switching from the usual order by time of email arrival to sorts on sender name or title, or searches for particular words or names. This is annoying, and to fast typists it runs the risk of incorrect response when the display is not in synch with what Apple Mail thinks is on the screen (most annoyingly, inadvertent deletions). I also have seen freezes and crashes.

This may be because I use POP3 mail for my personal domain and IMAP for three Gmail accounts and one (rarely used) iCloud account. It may also reflect other things that I do. I usually have several apps running (browser with many tabs open, word processor with multiple files open, PDF reader, calendar, scanner, and often a few more). It may be because I'm running High Sierra on a 2010 Mac Mini and an external FireWire spinning drive. I seriously doubt it could be that I am not synching mail with anything else. (I don't use an iPad or iPhone, and my MacBook Air has too little memory to try synching my email files.)

It's really very hard to pin down the causes of this sort of unstable behavior. Often it's some quirk in something we're doing. With email, it can be a web hosting firm or server doing something incompatible with Apple Mail, or a spam filtering app like SpamSieve. It may be some internal filtering we do. But I'm not the only one complaining.

FWIW, I will add that another symptom is erratic searching in Mail. Sometimes it does not find names I know to be in my mail files; other times it takes a while to find them. That may be part of the slowness I see with Apple Mail.
 


I'm curious why there is this persistent idea that Mail.app can not handle large quantities of email messages.
For me, it's always been unstable, even for small quantities of messages. I gave up using it many years ago, because my basic setup (three different IMAP mailboxes and the local "on my Mac" folder) would cause it to crash unpredictably all the time.

Maybe it's stable now, but I've been burned so many times I don't even want to bother trying. For those occasions where web-mail isn't acceptable, I run Mozilla Thunderbird which works just fine, even if the look-and-feel isn't very Apple-like.
 


Ric Ford

MacInTouch
Maybe it's stable now, but I've been burned so many times I don't even want to bother trying. For those occasions where web-mail isn't acceptable, I run Mozilla Thunderbird which works just fine, even if the look-and-feel isn't very Apple-like.
Postbox is a little nicer looking and features an integrated In Box, which is a big benefit (for me, at least). It still doesn't feel like a totally Mac-native application and lacks things I miss from Eudora, but it's pretty decent and I haven't had any reliability problems with it (in contrast to some bad experiences with Apple Mail).
 


Postbox is a little nicer looking and features an integrated In Box, which is a big benefit (for me, at least). It still doesn't feel like a totally Mac-native application and lacks things I miss from Eudora, but it's pretty decent and I haven't had any reliability problems with it (in contrast to some bad experiences with Apple Mail).
Postbox is nice, I agree, Ric. But I use a relative newcomer to macOS email clients: Spark. Very macOS-like interface and handles volumes of email quite well.
 


I have four email accounts, including an AOL account that was created when AOL was a Mac-only account. Every so often I do a search on some subject like Staples and delete all of the Staples ads.

My accounts show up on an iMac, laptop, and iPhone. I do not have issues with emails arriving. I have constant problems with the outgoing mail servers. It is really frustrating how little information you can enter into the mail preferences, as the set-up is automatic and tied to an Apple ID, then having the Connection Doctor say everything is ok, but when I send an email out, that email burps, asking me to use another outgoing mail server. The list presented to me is different from the list present in the mail preferences that allows you to edit the outgoing mail server.
 


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