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Old 28 Dec 2016, 02:40 PM   #1
camner
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Saving mail sent from iPhone (outside of Mail app) in Sent folder...

I use the FastMail app on my iDevices, but my question is about how to set things up so that mail sent, say, when one uses the "Share" button on an iDevice to send a email that shares a web page, for example. I want emails sent in this fashion to have a copy left in the Sent mail FM folder.

My current setup is this:
1. I have the default SMTP server on the iDevices set to the FM SMTP server
2. I have FM options set so that any email that gets sent through the FM SMTP server has a copy put in the Sent folder.
3. I then have all the various IMAP clients on iDevices and computers set so that they do NOT store a copy of sent mail in the Sent folder (so I don't get 2 copies!).

This seems unnecessarily complex. Is there an easier approach?
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Old 28 Dec 2016, 11:41 PM   #2
jhollington
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From what you describe, I can't see any reason why this shouldn't be working properly, so I'm probably missing something here in either your configuration or how you're doing things.

To be clear, when you say "I have FM options set so that any email that gets sent through the FM SMTP server has a copy put in the Sent folder." are you sure you've checked off the Save a copy when sending through 3rd party email clients?

If you're using multiple identities, you'll also need to make sure that you've enabled this option on all of the identities where you want this to happen — in particular whichever identify is the one you have configured in your iOS Mail settings.

You say you're using the FastMail app, so I assume that normally you send mail from your iDevices solely through the FastMail app, except when you're using things like built-in sharing tools, correct?

I'm guessing messages sent through the FastMail app are landing correctly in your "Sent" folder?

How have you configured your account in your Mail settings on iOS? There actually isn't a setting on the iOS side to not save messages in your Sent Items folder, so at that point I'm assuming that you're either not using an IMAP account or you've configured your "Sent Mailbox" to be a folder on your iPhone/iPad or your Trash folder (in which case you're still technically getting a duplicate — it's just ending up saved locally only or landing in your IMAP trash folder).

IMHO, the "easier" approach is probably just to NOT use the Save a copy when sending through 3rd party email clients setting and let IMAP do its thing from your iDevices and other IMAP clients. It will push the message into your "Sent Items" folder after sending, and the FastMail app on your iDevices will pretty much do the same when sending from there.

The only small downside is that your "Sent Items" folder doesn't provide a verification that your message was actually properly submitted via SMTP to FastMail (the IMAP save process is separate from the SMTP submission process), but I think that's a very small price to pay as the iOS Mail app should alert you if there's a problem on that end and just leave the message in your local "Outbox" folder until it can actually be sent.
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Old 29 Dec 2016, 11:13 AM   #3
camner
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Quote:
Originally Posted by jhollington View Post
From what you describe, I can't see any reason why this shouldn't be working properly, so I'm probably missing something here in either your configuration or how you're doing things
Or, more likely, I just didn't make myself clear!

Quote:
To be clear, when you say "I have FM options set so that any email that gets sent through the FM SMTP server has a copy put in the Sent folder." are you sure you've checked off the Save a copy when sending through 3rd party email clients?
Correct...I have checked off the Save a copy when sending through 3rd party email clients box.

Quote:
If you're using multiple identities, you'll also need to make sure that you've enabled this option on all of the identities where you want this to happen in particular whichever identify is the one you have configured in your iOS Mail settings.
Yes, though this seems to be happening by default. I just recently set up several new identities and I did NOT manually check that box! Perhaps that's the default action?

Quote:
You say you're using the FastMail app, so I assume that normally you send mail from your iDevices solely through the FastMail app, except when you're using things like built-in sharing tools, correct?
Yes

Quote:
I'm guessing messages sent through the FastMail app are landing correctly in your "Sent" folder?
Yes

Quote:
How have you configured your account in your Mail settings on iOS? There actually isn't a setting on the iOS side to not save messages in your Sent Items folder, so at that point I'm assuming that you're either not using an IMAP account or you've configured your "Sent Mailbox" to be a folder on your iPhone/iPad or your Trash folder (in which case you're still technically getting a duplicate it's just ending up saved locally only or landing in your IMAP trash folder).
You are correct. I have configured the "Sent Mailbox" to be a folder on the iPhone/iPad.

Quote:
IMHO, the "easier" approach is probably just to NOT use the Save a copy when sending through 3rd party email clients setting and let IMAP do its thing from your iDevices and other IMAP clients. It will push the message into your "Sent Items" folder after sending, and the FastMail app on your iDevices will pretty much do the same when sending from there.
I agree that this seems to be an easier approach. I think the issue for me is that I don't really know how to tell iOS which mail account to use when using the sharing tools. I have several accounts set up in Mail; how does iOS determine which one to use when sending email via the sharing tools?

Also, since outgoing mail is handled by an SMTP server, (1) how does iOS determine which to use when using sharing tools, and (2) since SMTP doesn't have anything to do with IMAP (AFAIK), how exactly would "let IMAP do its thing" actually result in a copy of the email ending up in the Sent folder of Fastmail?

Thanks very much for your extensive reply. Despite your great explanation, I'm still a bit unclear about a couple of things...
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Old 29 Dec 2016, 12:12 PM   #4
jhollington
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Okay, it sounds like you've got everything set up the way it should be.... I suspect the issue is about having multiple accounts configured....

Quote:
Originally Posted by camner View Post
Yes, though this seems to be happening by default. I just recently set up several new identities and I did NOT manually check that box! Perhaps that's the default action?
It could be, or more to the point I suspect it just copies the setting from your primary identity, as it doesn't get checked for me when I setup new identities (I use the IMAP save method).

Quote:
I think the issue for me is that I don't really know how to tell iOS which mail account to use when using the sharing tools. I have several accounts set up in Mail; how does iOS determine which one to use when sending email via the sharing tools?
When you're sending a messaging using the built-in Mail app, whether from the app itself or the sharing tools, tapping on the "Cc/Bcc, From:" line should expand it into three distinct fields, and then you can tap on the "From" field to select the account from which you want to send the message. The only trick is that they're identified by email address so this will be confusing if you have more than one account configured for the same address.

Quote:
Also, since outgoing mail is handled by an SMTP server, (1) how does iOS determine which to use when using sharing tools
iOS will use whichever SMTP server is configured as the "Outgoing Mail Server" for the Mail account/identity that you select to send the message (as described above).

Quote:
since SMTP doesn't have anything to do with IMAP (AFAIK), how exactly would "let IMAP do its thing" actually result in a copy of the email ending up in the Sent folder of Fastmail?
If you specify your "Sent Mailbox" to map to your "Sent Items" folder under "On the Server" (e.g. on FastMail), than the iOS Mail client will automatically file a copy of the sent message into your "Sent Items" folder using an IMAP connection, even when using the iOS share sheet; there's fundamentally no real difference between going into the iOS Mail app and sending a message and using the share sheet it brings up the same "New message" dialog and the same background processes are fired off to send the message.

To consider it another way, the iOS Mail app doesn't really treat IMAP and SMTP accounts as separate entities you basically configure "Mail" accounts, which are a combination of IMAP/POP for retrieving messages and SMTP for sending messages, bundled into a single "Mail" account that is identified by the "From" address associated with that account.

There's no way to set up just an SMTP server in iOS Mail without it being associated with an IMAP/POP account (note that you can have multiple SMTP servers for a single IMAP/POP account for fallback purposes, but you can't setup a "send only" account that just has an SMTP server and no associated IMAP/POP server).

So in other words, when you select the "From" address of "you@yourdomain.com" in the iOS "new message" dialog, you'll be sending though whatever SMTP server is associated with that account (under Settings, Mail), and you'll be filing a copy of that sent message in whatever folder is specified for "Sent Messages" for that account either a local folder or a server-based folder, according to whatever you've specified.
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Old 29 Dec 2016, 02:08 PM   #5
camner
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OK, this is much clearer! Thanks. I didn't know about the "tap on the CC/BCC From:" trick.

But, that leads to one final question...clearly when there are multiple accounts configured in iOS, it chooses ONE of them to be the default account to send from when using sharing tools. How does one choose that default account? [Because of work/home accounts I don't have the option of only having one email account set up on my iDevices, alas.]

{Not that it matters, but the original reason I set things up the way I did dates back to before the release of the Fastmail app for iOS. I have lots of folders set up and iOS Mail's way of navigating between IMAP folders is cumbersome, to say the least. So, I took the following, rather Rube Goldbergian, approach:
  1. Set up FM to forward all incoming mail to a Gmail account
  2. Set up Gmail on the iPhone to use the Fastmail SMTP server
  3. Configured Gmail to use my Fastmail email address as the "From" address
  4. Checked the box in FM so that any mail sent through the FM SMTP server would deposit a copy in the Sent folder
  5. Used the Gmail account via the iOS Mail app for receiving and sending emails from iDevices
This works, but is too complex for my taste and depends on my being available to configure all the family's iPhones and iPads this way!
}
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Old 29 Dec 2016, 10:53 PM   #6
jhollington
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Quote:
Originally Posted by camner View Post
OK, this is much clearer! Thanks. I didn't know about the "tap on the CC/BCC From:" trick.
Yeah, it's a little hidden, but it's definitely a handy one. It also works to choose which "identity" you want to use when you have multiple "From" addresses configured for a single account.

Quote:
But, that leads to one final question...clearly when there are multiple accounts configured in iOS, it chooses ONE of them to be the default account to send from when using sharing tools. How does one choose that default account?
Go into the Mail section in the iOS Settings app and scroll down to the very bottom below "Signature" you should see "Default Account" and you can choose it from there (note that this option only appears if you have more than one Mail account configured in the first place).

Quote:
{[i]Not that it matters, but the original reason I set things up the way I did dates back to before the release of the Fastmail app for iOS. I have lots of folders set up and iOS Mail's way of navigating between IMAP folders is cumbersome, to say the least.
While I'm not sure what you mean by "cumbersome" in your specific situation, you might want to take a closer look at Mail in more recent iOS versions, as there have been some nice improvements. For example, since iOS 7 you've been able to "pin" certain folders to appear up in the top of the list, right alongside your inbox and other system folders, as well as enabling "smart folders" at the top (to show you only unread messages, flagged messages, or messages with attachments, for instance). Also, iOS 10 added proper "full account" message threading so that you can now see a whole conversation thread regardless of which folders individual messages in the thread have been filed into. iOS 10 also added the ability to automatically suggest the most likely folder when moving messages (so if you're always filing receipts from Amazon into a "Receipts" folder, it will learn that behaviour and just offer up "Move to Receipts" as an initial choice when you choose to move any message that it recognizes as an Amazon receipt).

Further, FastMail implemented full iOS "push" support last year, and this supports not only the Inbox, but any sub-folder you wish to designate, allowing you to have messages that have been filed into or received into other folders to also be pushed to your iOS device.

Quote:
So, I took the following, rather Rube Goldbergian, approach .... This works, but is too complex for my taste and depends on my being available to configure all the family's iPhones and iPads this way!
Yeah, that's definitely complex, but it also sounds like what a lot of people did back in the early days of iOS Mail most often just to get proper "push" support for new mail. I'm not sure of your specific reasons for doing this, but I honestly can't see why you'd need to do this now over just using the native Mail app or FastMail app.

In other words, even if you're going to continue using the FastMail app, I'd suggest just configuring your iOS Mail settings to connect directly to FastMail over IMAP/SMTP and take Gmail right out of the equation.

In my case, while I keep the FastMail app on my iPhone for certain specific use cases* mostly easy access to preferences and more advanced searches I've found the iOS Mail app meets all of my daily email management needs, particularly with the many little improvements Apple has made it in over the past few iOS releases.
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Old 30 Dec 2016, 07:21 AM   #7
camner
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Originally Posted by jhollington View Post
Go into the Mail section in the iOS Settings app and scroll down to the very bottom below "Signature" you should see "Default Account" and you can choose it from there (note that this option only appears if you have more than one Mail account configured in the first place).
Yet another thing about iOS I didn't know....sigh

Quote:
While I'm not sure what you mean by "cumbersome" in your specific situation, you might want to take a closer look at Mail in more recent iOS versions, as there have been some nice improvements. For example, since iOS 7 you've been able to "pin" certain folders to appear up in the top of the list, right alongside your inbox and other system folders, as well as enabling "smart folders" at the top (to show you only unread messages, flagged messages, or messages with attachments, for instance). Also, iOS 10 added proper "full account" message threading so that you can now see a whole conversation thread regardless of which folders individual messages in the thread have been filed into. iOS 10 also added the ability to automatically suggest the most likely folder when moving messages (so if you're always filing receipts from Amazon into a "Receipts" folder, it will learn that behaviour and just offer up "Move to Receipts" as an initial choice when you choose to move any message that it recognizes as an Amazon receipt).

Further, FastMail implemented full iOS "push" support last year, and this supports not only the Inbox, but any sub-folder you wish to designate, allowing you to have messages that have been filed into or received into other folders to also be pushed to your iOS device.
I definitely have NOT kept up with iOS Mail's improvements over the years. Once FM's app came out, I pretty much have ignored Mail. I should take a closer look!
Quote:
Yeah, that's definitely complex, but it also sounds like what a lot of people did back in the early days of iOS Mail most often just to get proper "push" support for new mail. I'm not sure of your specific reasons for doing this, but I honestly can't see why you'd need to do this now over just using the native Mail app or FastMail app.

In other words, even if you're going to continue using the FastMail app, I'd suggest just configuring your iOS Mail settings to connect directly to FastMail over IMAP/SMTP and take Gmail right out of the equation.
I set things up the way I did for just this reason (Push) as well as being able to view FM messages more easily on iDevices by using the Mail app to connect to Gmail. I agree that there is no need any longer for Gmail, and I have the account turned off, though it is technically still on my phone (for many years I was using Google Calendar, though recently switched to iCloud calendars).

Thanks again for taking the time to write such complete responses. I appreciate it!
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Old 30 Dec 2016, 11:17 PM   #8
jhollington
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I definitely have NOT kept up with iOS Mail's improvements over the years. Once FM's app came out, I pretty much have ignored Mail. I should take a closer look!
Yeah, there have been some nice improvements, especially in more recent versions — I think a lot of it is driven by Apple's desire to be a real player in the business and enterprise space, where the built-in Mail client is much easier for most large organizations to deploy and maintain.

However, since the improvements are rarely earth-shattering compared to everything else that comes with a major iOS update, they're most often on the sidelines, so you don't see too many reports on them — they're just not as "sexy" as stickers in Messages, for example

That said, while I've dabbled in other clients off and on, I've generally preferred to stick with the built-in Mail app as of course it's the most tightly integrated, and also has provided the best reading experience of any Mail app since the beginning — especially where complex HTML messages are concerned. As a result, I try to stay up on the changes, and have covered them in my own series of iOS feature articles over the years — iOS 7 Mail probably saw the most significant set of improvements in recent years, but iOS 8 Mail brought enhanced swipe gestures which added a huge usability boost IMHO, along with smart contact and calendar event recognition, iOS 9 Mail added support for PDF markup and adding attachments from iCloud Drive and other third-party file storage providers like Dropbox, and iOS 10 Mail added account-wide conversation threading, quick mailbox filters, and smart filing of messages.

Factor in native push support with FastMail, and the bottom line is that the built-in Mail app has pretty much reached the point where I would no longer even consider using anything else. Not to disparage FastMail's own native iOS app, but I find the built-in Mail app to be faster, more tightly integrated with iOS, and you get full offline access to your messages (as long as they've been previously downloaded, but with native push, that's not a problem, and FastMail and iOS Mail even let you push folders other than the Inbox). The native client is more powerful for searching your mailboxes — especially if you're doing complex searches —*but iOS Mail is no slouch in this area either, especially considering the great work FastMail has done supporting IMAP search on the back end.

It's also worth noting that FastMail deserves huge kudos for implementing iOS Mail push properly — even Apple's own iCloud service is a very weak implementation compared to how FastMail has done this. For example, iCloud will push when you receive new messages, but it won't push out changes such as marking messages read or deleting them. This means you end up with a stale badge count on your iPhone or iPad if you're reading your messages on another device. FastMail pushes a complete reconciliation of everything that happens in your mailbox — leave your iOS Mail app open to your message list, mark a message read or flagged from your desktop, and you can actually watch it change within a second or two on your iPhone. It's really quite magical.

Quote:
I set things up the way I did for just this reason (Push) as well as being able to view FM messages more easily on iDevices by using the Mail app to connect to Gmail.
Yup, that was a common use-case scenario for a lot of people. I didn't want to forward in my case, so it's one of the things that had me go over to Gmail entirely for a while years ago, and then eventually give up on that and setup my own macOS Mail server (and figure out how to engineer "proper" push support into it ). Once FastMail began offering its own proper push support, the last major incentive I had to run my own mail server was gone, and I just moved everything back over here and haven't looked back since.

Quote:
for many years I was using Google Calendar, though recently switched to iCloud calendars
You may also find it worthwhile to take a look at FastMail's recent CalDAV and CardDAV improvements. You can now not only host your contacts and calendars at FastMail, but sync them to your native iOS Contacts and Calendars apps, also with complete push support. I haven't fully pulled the trigger on that myself — I'm still on iCloud for my Calendars, at least, since I share a few with non-FastMail users and it's just easier to keep everything there — but it's definitely worth a look if you wanted a tighter integration of everything in one service. It's especially valuable for your contacts, as you can then more effectively take advantage of server-side rules that filter based on contact.

Last edited by jhollington : 30 Dec 2016 at 11:26 PM.
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Old 31 Dec 2016, 02:16 AM   #9
camner
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Originally Posted by jhollington View Post
Factor in native push support with FastMail, and the bottom line is that the built-in Mail app has pretty much reached the point where I would no longer even consider using anything else. Not to disparage FastMail's own native iOS app, but I find the built-in Mail app to be faster, more tightly integrated with iOS, and you get full offline access to your messages (as long as they've been previously downloaded, but with native push, that's not a problem, and FastMail and iOS Mail even let you push folders other than the Inbox). The native client is more powerful for searching your mailboxes especially if you're doing complex searches *but iOS Mail is no slouch in this area either, especially considering the great work FastMail has done supporting IMAP search on the back end.
I took a brief look at iOS Mail after reading your earlier reply, and I have to say that I agree that it is far better than earlier incarnations. That said, I wasn't wowed enough to say "This is definitely better than the FM app," but perhaps that is due more to familiarity breeding respect rather than contempt!
Quote:
Yup, that was a common use-case scenario for a lot of people. I didn't want to forward in my case, so it's one of the things that had me go over to Gmail entirely for a while years ago, and then eventually give up on that and setup my own macOS Mail server (and figure out how to engineer "proper" push support into it ). Once FastMail began offering its own proper push support, the last major incentive I had to run my own mail server was gone, and I just moved everything back over here and haven't looked back since.
I briefly toyed with the idea of setting up my own server, but decided against it, as that was heading MORE, rather than less, in the direction of "I am the only one around who has a prayer of maintaining this and without me no one in the family gets email!"

Quote:
You may also find it worthwhile to take a look at FastMail's recent CalDAV and CardDAV improvements. You can now not only host your contacts and calendars at FastMail, but sync them to your native iOS Contacts and Calendars apps, also with complete push support. I haven't fully pulled the trigger on that myself I'm still on iCloud for my Calendars, at least, since I share a few with non-FastMail users and it's just easier to keep everything there but it's definitely worth a look if you wanted a tighter integration of everything in one service. It's especially valuable for your contacts, as you can then more effectively take advantage of server-side rules that filter based on contact.
What deters me here is that my wife, though on Apple iDevices, has a Windows 10 PC and I need to have a system that allows her to access our joint contacts, our joint calendars, and email. She uses Outlook for email and contacts, and iCloud (web based) for calendaring.

By the way, two questions not quite on original topic.

1. It took me a while to puzzle out how to create one family address book (with separate groups for "mine," "hers," and "ours" contacts). Her iCloud ID is used for all contacts (that's because Outlook and Windows 10 can only sync with one Apple ID via the iCloud sync Apple has created for Windows), and I have her Apple ID set up on my iDevices and the household Macs as an additional iCloud account. Is there a better way to handle this, do you think?

2. I'm curious what you use on your desktop(s)/laptop(s) for email, calendaring, and contacts. I use BusyCal and BusyContacts, and I'm very happy with both. I currently use Postbox for email, but I'm not thrilled with it. I've tried various other clients (too numerous to list), and haven't really found anything I'm happy with.

Thanks again for your time!
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Old 3 Jan 2017, 03:58 AM   #10
jhollington
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I took a brief look at iOS Mail after reading your earlier reply, and I have to say that I agree that it is far better than earlier incarnations. That said, I wasn't wowed enough to say "This is definitely better than the FM app," but perhaps that is due more to familiarity breeding respect rather than contempt!
Well, to each their own to be fair, and of course familiarity counts for something

For me it was primarily the tighter integration and more "native" feel of the built-in iOS Mail app, not to mention that messages are downloaded/synced and saved offline so they can still be accessed when I have no coverage —*I've generally preferred the iOS Mail client's overall UI for years, but obviously early iterations were also more limiting. There are also a few features like "VIP" notifications that aren't even available in most third-party mail apps (e.g. the ability to only get push notifications from specific contacts rather than for every new message — a feature that I find extremely handy).

Quote:
I briefly toyed with the idea of setting up my own server, but decided against it, as that was heading MORE, rather than less, in the direction of "I am the only one around who has a prayer of maintaining this and without me no one in the family gets email!"
Yup, that was one of the big things that always dissuaded me off and on over the years, along with the fact that I ended up being a victim of the stability of my ISPs home connection and other factors.

Quote:
What deters me here is that my wife, though on Apple iDevices, has a Windows 10 PC and I need to have a system that allows her to access our joint contacts, our joint calendars, and email. She uses Outlook for email and contacts, and iCloud (web based) for calendaring.
Well, CalDAV and CardDAV are the same protocols used by iCloud, so there aren't a lot of differences whether your use FastMail or iCloud in that respect, other than the web-based interface, and I guess that's a matter of personal preference.

That said, iCloud's implementations do have a couple of advantages for iOS users.... VIP contacts only sync between devices if you're using iCloud — FastMail doesn't seem to support this (yet) and I wouldn't be surprised if there's something Apple-specific hiding under the hood on this one.

iCloud Calendars are also a bit more tightly integrated into iOS as opposed to other CalDAV services, and of course if you're sharing calendars with iCloud users, you'll need an iCloud account to do that anyway.

Quote:
1. It took me a while to puzzle out how to create one family address book (with separate groups for "mine," "hers," and "ours" contacts). Her iCloud ID is used for all contacts (that's because Outlook and Windows 10 can only sync with one Apple ID via the iCloud sync Apple has created for Windows), and I have her Apple ID set up on my iDevices and the household Macs as an additional iCloud account. Is there a better way to handle this, do you think?
Sadly, that's probably the only real way to handle this with iCloud Contacts in a Windows world. Even in a Mac-only world, you're still dealing with secondary iCloud accounts if you want to share contacts. Hopefully Apple will someday allow contact sharing.

That said, FastMail's CardDAV does support shared address books, so that might be a way to do it more easily. You'd still have to sync them to Outlook in some manner —*sadly, Outlook does not offer any native CardDAV support, but there are several CardDAV plug-ins for Outlook that could work for this purpose.

Quote:
2. I'm curious what you use on your desktop(s)/laptop(s) for email, calendaring, and contacts. I use BusyCal and BusyContacts, and I'm very happy with both. I currently use Postbox for email, but I'm not thrilled with it. I've tried various other clients (too numerous to list), and haven't really found anything I'm happy with.
I like BusyCal and BusyContacts in principle, and own licenses for both. I used them for a while, but I honestly found them to be more complex than I needed for my purposes, and went back to the standard macOS Calendar and Contacts apps. This is another area in which a few slight improvements — and tighter integration into iOS sync via iCloud — have made a big enough difference, and again I tend to like the cleaner and more minimalist interfaces of these apps. Again, though, my contact/calendaring needs aren't that sophisticated
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