Share your email problems and insight for an MPU episode

I’m an Outlook user on Mac/IOS. It’s a good client if you’re in the MS world where I’m stuck because of work rules.
I’m constantly challenged trying to get info out of there to Omnifocus, Notes etc.

I dream of a workflow that I can get emails easily (emphasis on this word) into Omnifocus with a link back to the email, flag emails in Outlook that need a response etc.

I can use apple mail at work but I find it clunky because of a lack of a share sheet.

Adding a share extension/sharesheet, and implementing server side filters, to Mail.app would be enough for me.

If it’s Christmas, Apple could acquire Sanebox (Workflow-style) and just make it part of the system.

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On Mac, I primarily use Gmail’s web client, which isn’t awesome but has the benefits of being the first-party client. Really, really dislike the composer, though, and I don’t see why Google continues to enforce a maximum line length in plaintext emails by inserting hard line breaks. Ugh.

Mail.app does the job for a secondary account, but I have nothing good to say about it.

On iOS, I almost exclusively use Outlook mostly because its Focused Inbox does a ridiculously good job at figuring out which emails to notify me about, but also because it’s swipe gestures “feel” right. I’m not really a fan of how iOS’s native UITableCell swipe gestures feel.

If I sent more emails, I’d probably use Drafts, but I tend to only send quick replies to existing threads, so it’s a lot easier to hit R, type my message and then ⌘⏎ to send.

When searching archived emails, I really have to go back to Gmail’s web client. Outlook on iOS fails to find what I want too often, and Gmail on iOS does a poor job auto-completing long label names.

I need some guidance on switching from POP3 to IMAP email. My server is Verizon (which is to say AOL/Yahoo under the hood); my client is Outlook on my iMac. With the proliferation of devices (iPhone, iPad, and a MacBook Air), the POP3 functionality (download of email separately to each device) is a nightmare. I have a GMail account, but I’m reluctant to switch over for two reasons: 1) What do I do with 20 years of folder-based email? and 2) Can I replicate a file and folder structure in GMail that is robust enough for work and personal email archives?

My primary mail account is G Suite. On both the Mac and iPad Pro, I flip between the native GMail app and Mail.app, depending on what I am doing. I find this system works well.

The native Gmail interface handles Gmail’s labels better than mail.app. On the other hand, mail.app gives me access to desktop notifications and my Mac address book.

I’m thinking about transitioning to Malplane to get the best of both worlds, but the system I have works well so I’m in no rush.

I’m using gmail, exclusively and have been for years, via the Gmail app for iOS and iPadOS, and recently using Made for Gmail for iOS. Gmail has the best Spam filtering, hands down. I love filtering my mail into folders, but do find the setting for managing filters to be a bit clumsy.
I gave up on Apple mail because of its very proprietary format, lack of flexibility, difficulty saving it offline, etc. I would need a very compelling reason to go back to Apple Mail.

I can’t address using Outlook as I use Apple Mail. But I did recently switch a POP3 account to IMAP, and I use a mix of POP3, IMAP, GMail, and (until recently) Exchange accounts. Most accounts I only want to read from one system, so those will stay with POP3.

At least with Apple Mail there is no way to directly change from POP3 to IMAP. The mail provider account doesn’t care – it keeps all mail on the server unless deleted via a POP3 fetch/delete. But Mail required that I create a new mail account specifying IMAP. Then I created folders (mailboxes) in the IMAP account matching what I had locally (“On My Mac”) for the POP3 account. Finally I dragged and dropped all the messages from the local folders into the IMAP account folders.

I’ve also gone the other way when IMAP style accounts were going to be deleted – I just drag and drop all the messages into a local folder/mailbox then I don’t lose any of the messages that were in the discontinued account.

I daily monitor 20+ email accounts…I couldn’t do it without Mailmate. It rocks. I deal with all my mail accounts in 10 minutes tops (not bad for 1500+ emails a week). Filtering, search, encryption, integrations, spam detection…all awesome. One issue I do have is syncing contacts from the various accounts to my iMac and my iPhone where I use spark. I just not have found an efficient, reliable way to get it done.
On my wish list for future functionality is a sidebar to appear when I am reading/composing and email with the latest emails from the recipient as well has social media posts…so I don’t get blindsided by something that has happened in the last 24 hrs that would affect the content of…or whether I should send an email at all. Listening to the episode was a nice walk down memory lane. I have used sunrise, dispatch, thunderbird, outlook, Edison, apple mail, airmail. All had some good points but had some spectacular failures as well.
Great episode. Thanks.

There is still a place for POP email.
For example for those who have an intermittent internet connection where you live or travel. Take a Look at the “Activity” in Mail and notice how much traffic is going back and forth to synchronize the IMAP account(s). This requires a decent internet connection to work. POP is just a one way download and some upload of you happen to have email in the out box. Depending on the situation you can set the email client to leave the attachments or on the server or not. If you disable downloading attachments your device will only download text and leaves the large attachments and other junk behind on the server.

Then there is privacy.
In some cases you might not want to have a large cash of you your personal communication sitting on a server. If you set the POP client to delete the email after downloading it will leave an empty email box behind.

Of course this has consequences for your convenience and you will have to take care of backing up your emails locally if its important to keep a record of your email communication.

Keep this in mind when planning your sebatical and travel in remote places with poor internet connection. Create a POP email account and set some tight rules on your main email account(s) to forward select email’s to this “travel” account.

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While traveling with a “travel” computer you can read POP mail either online (if the mail provider has a web based mail app) or configure Mail on the travel computer to fetch mail and not delete on the server. I’ve done fine for decades with POP doing just this.

I also find mailmate is awesome especially if you have a lot of email accounts. What do you use on iOS to manage email from 20 email accounts?

I use Google, but I do not like their policies.
First, it drops its agent into OS that ‘secretly “calls home” on a regular basis and downloads updates to your Google software without either asking before, or notifying you after, doing so. In Developer circles, this is considered very shady practice’.
What really drives me nuts as a frequent traveler is that Gmail oftentimes refuses my password upon landing in another country and want to send me an sms or call me. I often replace my Telia sim with a local one, so that is a really annoying precaution.
I also use Yahoo, and I do not like that hijackers impose its search engine on a large scale. I know that Yahoo does not hijack my browsers, but still they might fight the criminal more effectively. I mean scams as described here: Remove Yahoo Search redirect virus from Mac - MacSecurity