Help me manage many e-mail/calendar accounts

January 30, 2024 3:37 PM

I am struggling with managing various work-related and personal email accounts, currently managed across different applications and browsers. Missed meetings, forgotten emails etc result. There must be a way to put all of these in one place. I want to be at least reasonable sure there's a way to avoid 'crossing the streams' (eg replying from the wrong account). Please hope me?

I currently use the following:
- personal email - Gmail
- volunteer email - integrated into personal email on Gmail
- employer email 1 - Outlook online in Chrome
- employer email 2 - Outlook online in Safari
- employer email 3 - Outlook online in Safari (have to log out of email 2 first)
(employer emails are three different companies with the same ownership and I have a role in each company)
- own business email - domain owned by me, mail on Outlook installed on desktop and laptop.

The employer emails are particularly annoying, as they're each tied to a MS 365 account and that piece of garbage service doesn't allow concurrent logins, hence the use of multiple browsers. The volunteer email integrates well with my personal email in Gmail and the only thing I have to remember is to make sure the correct 'from' account is selected before sending. No big deal for an account that I hardly ever send from, but a whole other level if I add another four accounts and very much don't want to mix personal email with employer email.

I have searched all over the place for a solution that will put all of the above emails and associated calendars into one place. The only viable thing I can come up with is to just use Gmail and set up rules to put mail related to each address into its own folder/s. I'm not sure if that would mean I can have everything in a single Google calendar, including RSVP to meeting requests adding to the calendar automatically.

I can't imagine this isn't a solved problem. I'd prefer something free, but willing to pay a small amount if it frees me from the constant anxiety that I've missed a meeting, email or deadline (and, to be honest, from actually missing meetings, emails and deadlines).

posted by dg to Computers & Internet (16 answers total)

You can subscribe to multiple calendars from multiple sources in Google Calendar. I have no experience with Outlook Online, but I've found the feed for my work calendar stream (from Outlook) and subscribe to that in Apple's Calendar app; gCal can do the same.

Gmail can fetch e-mail from other accounts, and can send as those accounts; setting up the former isn't that hard; setting up the latter is a little more work, and you need to be careful to switch the account you're sending as, obviously.

For that matter, Apple Mail can also connect to multiple mail accounts and send/receive with all of them. It has a unified inbox view, but it also keeps each inbox separate.
posted by adamrice at 4:09 PM on January 30, 2024 [1 favorite]

Adamrice is absolutely in theory correct. HOWEVER, depending on your employer settings, this may not be quite that straightforward. My employer is now using Outlook and the Microsoft Auth app and I'm constantly having to reenter my password and do 2FA again to get into my calendar from Apple's calendar app, and my Google calendar won't read my Outlook no matter what link I feed to it, what incantations I mutter, and how I hold my mouth. So just a heads up that hopefully it works for you, but it may not.

I'll be watching the answers in desperation interest.
posted by joycehealy at 4:21 PM on January 30, 2024 [2 favorites]

Given the three employers have the same ownership, would it be acceptable to consolidate the three accounts? eg account 2 and account 3 forward incoming mails to account 1?
posted by zippy at 4:27 PM on January 30, 2024 [1 favorite]

There are a couple of interesting tools available for juggling multiple calendars and accounts like that.

https://calendarbridge.com/ is a SaaS service that duplicates events (sync's) from one calendar to another and works for me despite all of the iCal lockdown / 2FA login codes my corporate IT has set up. I use this to send my personal events froma a Google Calendar into my work Outlook365 calendar as private events so that people automatically see me as busy (but without any details) when they're scheduling. I also have my work events sychronized into my personal calendar with all the details and join links so that I have everything in a single glance.

https://sigmaos.com/ is a browser designed to make accessing many different SaaS tools and login indentities quick and easy. The idea is that you would create a new workspace for logins, pin the calendar and email websites, and jump between them instantly. (FWIW, you can also do this with Chrome/Edge profiles with a few more clicks for profile switching.)
posted by QuixoticGambit at 4:36 PM on January 30, 2024 [1 favorite]

Response by poster: I've looked into that zippy. Unfortunately, it would remove the ability to respond from the same address as was sent to and my boss doesn't want to have emails mixed between the companies. There may be a solution to that, but I have no faith whatsoever in our one-person IT team to implement anything more complex than creating a new account. Any solution is going to have to be implemented by me alone.
posted by dg at 4:39 PM on January 30, 2024

Your employer should be able to set it up on the admin side of Microsoft so that your three email addresses are all connected to one account (and then help you set up so you can reply to each email according to where it was directed or can choose which email you send from). That might involve forwarding, if these three companies have separate IT infrastructure, but should be something whoever is in charge of IT should be able to sort out.

For the own business email, you should be able to just have Gmail check it via POP or IMAP and then set that email as a "Send as" option in Gmail.

That gets you down to two email accounts, which seems reasonable unless you really want to mix your personal email with your work email.

For your calendars, I think you need to add the work events to Outlook calendar and the personal event to Google Calendar; it won't make sense to try to add events from Outlook to a Google Calendar. You should then be able to share the Outlook calendar with your Google Calendar and have those events appear in Google Calendar as well.
posted by ssg at 4:46 PM on January 30, 2024 [1 favorite]

Gmail has an option to default to replying from the same address that an email was sent to. You can find it in Settings, under the Accounts tab, at the bottom of the "Send mail as" section.

I would strongly recommend using the "not an alias" checkbox when adding additional sending emails to Gmail. That connects to the "real" email account instead of sending from your personal Gmail with a very transparent "pretend I'm this other email" sticker.

If you share a Google Calendar with another Google/Gmail account, you'll be able to see all the events and RSVP. I just confirmed that when I am logged into my personal GMail, when I RSVP to an event that is on my professional GMail calendar that has been shared, the corporate Outlook account that sent the event invitation got the RSVP email from the same professional GMail account that was invited.
posted by QuixoticGambit at 4:54 PM on January 30, 2024 [1 favorite]

Silly question: why not install desktop Outlook and add all of the MS365 and GMail accounts to that? Is there a reason that you need to access these inboxes in your browser?
posted by QuixoticGambit at 4:57 PM on January 30, 2024 [3 favorites]

Firefox containers will let you login to the same service with different accounts in the one browser window at the same time. Which would reduce one or two niggles there.
posted by deadwax at 7:28 PM on January 30, 2024 [4 favorites]

Response by poster: QuixoticGambit, not a silly question and, if that's what it takes to make it all work, that's what I'll do. I do need to access my personal mail on phone, but that's no challenge anyway. I do have desktop Outlook installed already and use it for my business account.
posted by dg at 7:30 PM on January 30, 2024

This was why I ended up in the Apple universe of things. Apple Mail isn't great, and has definitely had its problems over a few years, but it's currently still the best for me. Although I'm not sure exactly how well it ties into the Office365 stuff, but I get the impression it should be okay.

I also used to have five calanders all overlaying into my single calander app (incl 2 shared ones), and each had its own colour scheme, for easier to distinguish between at a glance (business A was green, B was blue, etc).

Personally the reason I still use AppleMail is because I can check my 15 different IMAP (incl one Gmail, and one iCloud) email accounts inboxes, in one 'all inbox' window very quickly and easily. I'm very particular about moving things out of my inbox into specific sub-folders in the relevant accounts, once it's been dealt with, invoice paid and filed, etc. So all my inboxes are maintained to keep pretty empty.

Any emails consistently reply from the business mailbox they were sent to. I have default different signatures for each mailbox acount relevant to that business only. And it works (and syncs) across my laptop, phone, and desktop (each very different ages of hardware).

Thr only time I have issues with using the potentially wrong account when generating a new email rather than a reply. But I have it set so my signatures for that business are only available when sending from that account. Otherwise it's from my default backup 'myname@generic-email' which is neither personal nor business, just in case I forget to check the signature (and my generic-email has a similarly generic signature).

I do appreciate this isn't right for everyone though.
posted by many-things at 2:13 AM on January 31, 2024 [1 favorite]

Since you are already using multiple browsers for your work accounts, it might be easier for you to consolidate those in Microsoft Edge. It’s Chrome-like but integrated with Microsoft products. You could create separate profiles for each work account (with different colour themes to easily differentiate between them). Then, you just open each profile in a separate Edge window. Choose one of those to log into your non-work accounts as well. Edge has doodads such as sidebar access to Outlook that make it a little bit nicer for that purpose than vanilla Chrome or Safari, and also supports Chrome extensions.
posted by jknx at 9:52 AM on January 31, 2024 [1 favorite]

nth-ing Firefox Multi-Account Containers, which has colours for each tab session and you can give each container meaningful names and emojis.

Chrome let's you have multiple sessions with distinct logins, but it's not as clear which is which and leaves a gap for your confusion. Edge is a clone of Chrome and I wouldn't recommend any extra Microsoft you might be able to avoid.
posted by k3ninho at 3:03 PM on January 31, 2024 [1 favorite]

You can definitely add multiple accounts to the Outlook desktop app, it's pretty easy! I have two work emails and a school email, all through Microsoft webmail. I have two work laptops and a personal phone. My breakdown:

I've added one work email and the school email to the desktop Outlook app on Computer 1. I've also added these same emails to the Outlook app on my phone. I get notifications of emails and meetings through Computer 1, my phone, and an Apple Watch, so I feel well aware of what's happening there.

The second work email requires a physical token to log in on Computer 2 and can't be added to the Computer 1 or my cell phone. The only place I access this email is Computer 2, either from Computer 2's desktop Outlook app or a browser on Computer 2. I just have to keep Computer 2 open and nearby and check it frequently if I'm on Computer 1.
posted by airplant at 4:47 PM on February 2, 2024 [1 favorite]

Response by poster: Update:
I've set up all the work-related accounts in Outlook (desktop), along with some automatic categorisation to flag which account messages come from. I've left my Gmail account out of that at this stage. All seems to be working well so far. I haven't set up access to any of the work accounts on any mobile device, which is fine because I try to keep work to work time when I'm in front of either my laptop or desktop computer anyway. I will at some point try setting the work accounts up on my phone via Outlook for the rare occasion when I want to access work email at places like airports.

I'll update again before the question closes.
posted by dg at 5:36 PM on February 21, 2024

Response by poster: Final update:
After a few months of using the above configuration, all is working well and I feel much better organised!
posted by dg at 9:15 PM on May 26, 2024