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ISO… The Perfect Email

October 4, 2009

Recently I have been on a quest to find the perfect email client/service… one that will allow me to consolidate and handle all of my email accounts in one place and have access and full functionality to that place from any device (computer/laptop/phone) on any network.

Even though I have weaned and consolidated accounts, I still have about a half dozen email addresses that I actively use for personal email — a few through my ISP, a couple from my web sites/domains, a Yahoo mail account tied to my Yahoo user ID, a junk mail account, etc. For years I used Outlook Express to pull all of these into one place for reading, replying and filing. Other than the fact that Outlook Express does not have a calendar, the program met all of my needs as far as mail and contacts. I especially like the ability to create complex rules/filters, and to create folders in a hierarchy rather than just a big long list. Over the years, I had set up a rather elaborate automatic sorting & filing system that really helped make handling incoming mail nearly effortless.

The Outlook Express client worked great as long as I was primarily using one computer to access my personal mail. Even once I started occasional use of my laptop for traveling, it still worked having the OE client on both and having one set only to retrieve messages but not delete them from the server so they would still come to the primary for filing. Granted, this was a bit cumbersome as at the time, Comcast (my home ISP and primary mail provider) did not allow you to send email from your Comcast email account from within a client-based app (i.e. Outlook Express) if you were not on your Comcast ISP connection. So if I was away from home, I could retrieve my messages into the OE client on my laptop, but not reply to any of them using the Comcast address they had been sent to. Their solution to this was web mail access, which a few years ago was an okay work-around as their web mail was relatively simple and flexible. But a couple of years ago, Comcast “updated” their web mail and the interface and flexibility of the new app is, in my opinion, worthless. I can no longer pull messages from all accounts into one inbox, rather need to log in individually to each account to be able to send replies from the account the message was actually received into. This being a bit of a pain, I found myself neglecting to reply to messages and letting stuff go much longer than I should have.

A few years ago I began spending summers up at the cottage at camp, which presented its own set of of complications. I was still able to receive all of my mail into the OE client on my laptop, and even though Comcast had now opened up the SMTP end of things allowing customers to send from outside of their Comcast connection, outgoing SMTP is disabled on our work network (for good reason), so I still had the issue of not being able to reply to messages using my Comcast address unless I used that horrible web mail interface. Not to mention that using the OE client on my laptop to receive messages for extended periods of time meant huge quantities of already read and deleted mail to sort through on my home computer when I was there, a mundane chore which I let go and quickly lost control of. It just wasn’t working…

I started looking for an online mail service so I would have easier access to my mail — sending and receiving — via the Internet, from wherever I was, whatever network or machine I was on… I’m still looking for the perfect email service.

My Requirements?
– Need the ability to pull in other POP3 mail accounts, both to receive and send
– Must have the ability to create folders, preferably within a hierarchy, or at least do some sort of tagging
– Must have the ability to sort inbox and/or folder messages by different column headings (i.e. sender, date, etc.)
– Must have a built-in search function
– Must be able to set up rules/filters
– Preferably would have an integrated calendar and contacts
– SPAM filtering that really works
– Would prefer an archiver, but must at least provide the ability to export messages for archiving
– Automatic checking of all email accounts — yes, I am too lazy to hit the “check mail” button to get my mail (really it is not laziness, rather it is annoyance that anyone would make a mail client/service that does not at least offer PUSH as an option — for all accounts you have set up)
– Non-threaded conversations — at least the ability to turn off conversation threading… (more on this below)
– Availability of an ad-free version (yes, I would pay for this if all other needs were met)
– Adequate online storage space for messages so they are accessible from any machine on any internet connection
– (recent consideration) Must have an iPhone counterpart

Does this email app exist? If so, I have not found it yet. I’ve tried several, most of which are so lean they fall short on several points and really are not even worth reviewing, but I will talk about a couple of the more popular ones.

Gmail
I really wanted gmail to work for me, but after several months of trying to make it fit, I’ve jumped ship. I just cannot get used to the conversation threading. As an occasional user of newsgroups, I was not new to message threading, but while it seems to work fine with newsgroup messages where I don’t usually care if I miss a message or two and generally want to reply to the entire group, it does not work with my personal email where I do want to see every incoming message and often want to reply just to one person who has been part of the thread or forward to another person without having to send the entire thread. Furthermore in newsgroups, the messages are kept online, in some storage place outside of my email box, so there is no need for me to personally keep things for future reference. In my own email I often want to hang onto old messages (okay I am a bit of a pack rat), but don’t necessarily want to keep the entire thread of the conversation related to a message, which gmail does not allow for as the entire thread is handled as a whole. Admittedly there are many people who like the threading format and there are times I find it easier to follow a conversation this way, but to make gmail something I could functionally use as my primary email app, I would need the ability to turn this off. The other annoying thing about gmail is the inability to quickly sort my inbox and folders in different ways by simply clicking on the column headings since there are no column headings. Other than these two things, both of which are major limits to functionality in my opinion, I was very happy with gmail. I particularly like the labels (i.e. tags), which is far more flexible than folders (once you get used to it) as you can apply multiple labels to the same message.

PROS
– the user interface is clean and uncluttered
– fast
– generous free online storage space
– the SPAM filters are very effective
– the labels/tagging system
– the filter options are very flexible with the ability to apply multiple criteria and actions
– calendar, contacts and to-do list
– full-featured POP3 and forwarding support
– there is a built-in search (after all, it is Google)
– can be used with iPhone

CONS
– conversation threading
– inability to sort message by column headings
– search is not ‘string-based’ rather it is ‘word-based’; for instance, searching on ‘event’ will not bring back ‘events’ or ‘eventual’, etc. At times this is nice, but most times I find it counter-intuitive and limiting, particularly with plurals

As you can see, the pros far outweigh the cons, but unfortunately the cons are deal-breakers for me as far as being able to effectively use gmail as my primary email program.

Yahoo! Mail Plus
Having abandoned Gmail, I decided to give Yahoo! mail another look. I’ve had a Yahoo! mail account for years, just have never really used it for anything. Quickly I realized that the free version was missing several features I was looking for, so I paid the $19.99 for a year’s subscription to take advantage of more powerful SPAM filtering, POP3 access, mail forwarding, the elimination of ads and the ability to create more rules/filters. The plus mail also gives you what they call disposable addresses, which is a cool concept, I’m just not sure I need to remember yet another email address.

While Yahoo! mail is working out for me, I’m just not feeling the love like I did with Gmail, but I can’t really put my finger on the reason why… The interface is clean and uncluttered, which is really nice. It comes very close to meeting everything on my ‘wants’ list, although it does have a few quirks, which are really more annoyances than actual significant deficiencies. The criteria and action options for rules/filters is very limited and there is no hierarchy for folders, they just all end up in a big long alphabetical list. I’ve also noticed that moving between mail, calendar and contacts is not as seamless as it should be — maybe I’m just not seeing it, but I can’t figure out how to get from my mail to my calendar or contacts without using the buttons on my Yahoo! toolbar. This is an issue from within the address book or calendar as there are tabs for calendar, contacts and mail there. The other thing that is annoying is the way Yahoo! mail handles POP3 accounts — it doesn’t just PUSH the mail into your Yahoo! inbox, rather you have to manually click on the “check mail” button to get them. I got around this by using forwarding on my POP3 accounts instead of setting them up for POP3 retrieval from within Yahoo! mail, but this would be a liability if you didn’t have the ability to set up the forwarding on the other end — it would be very easy to forget to “check mail” since your inbox is seeing new messages (those sent natively to the Yahoo! address). An internet search did yield some third-party apps and plug-ins that will do the checking for you, but it just seems like this should be automatic in the mail program itself.

PROS
– clean, uncluttered interface
– integrated calendar and contacts
– unlimited online storage space
– POP3 and forwarding (with paid Plus product)
– ability to create folders (have not been able to find a published limit, but I have quite a few)
– ability to create filters/rules (100 with free account; 200 with paid account)
– effective SPAM control (MUCH better with paid account)
– built-in search
– ability to sort messages in inbox and folders by clicking column headings
– iPhone counterpart

CONS
– have to pay for the Plus product to get POP3 access, forwarding and decent SPAM filters (all things that come free with gmail)
– no hierarchy for folders
– limited criteria and action options for rules/filters
– moving around between mail and calendar/contacts is not intuitive
– requires manual checking of POP3 accounts or installation of third-party app to do this for you
– slower than Gmail

None of the cons are deal-breakers for me, so for now I’m sticking with Yahoo! Mail Plus, at least for a few months to give it a proper test run, or until something better catches my attention.

One thing I did want to note is that I am not completely comfortable with the TOS of either Gmail or Yahoo! mail as they both take some pretty broad liberties with your private information. I do feel a bit uneasy having so much personal information stored in their reserves, but it is the Internet…

Do you have a mail client/service that is really awesome? I would love to hear suggestions! Also, feel free to correct me if anything I’ve said in relation to Gmail or Yahoo! mail is inaccurate or if I have missed an obvious feature, etc.

Posted by Deb  No Comments »

Topics: geek speak, productivity

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