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Things Wrong with Apple’s Mail

July 25th, 2009

I am long through with using Eudora as my email client, but I am still not satisfied with Apple’s Mail app. There is too much missing from a program which, by now, should be much better-managed. Like the Mail app on the iPhone, it simply doesn’t do things right–obvious features are left out, and very annoying bugs or badly-run processes are left to continue from version to version. Like making a mouse, Apple fails repeatedly at getting the email app right.

First of all, Apple’s Mail does not allow you to stop a send-mail process. For example, if you click “Send” for an email and then a moment later realize that you used an outgoing server which would not work from your location, then you are screwed, for the next long while at least. Mail will simply sit there are attempt to complete an impossible process, not allowing you to stop the process, recover the email draft, reset the outgoing server, and getting the mail sent right away.

No, instead, you have to wait for an indeterminate amount of time–sometimes longer than 5 or even perhaps 10 minutes–for Mail to figure out that it can’t do it, when it finally releases your message. Your only alternative is to completely re-write the email and send it correctly this time–which you don’t know is necessary, as the original email could pop back at any time. This is incredibly frustrating.

Apple claims that you can kill the process, but I have tried on several occasions, and it never works.

Second: you cannot edit received mail within the app. This is presumably to preserve the original email as a record. Eudora did not limit you that way, but Apple does. I find it frustratingly stupid. If I really wanted to fake an incoming message, I could just access the record directly and do so with a text editor. Keeping me from doing it in Mail doesn’t keep it from happening, it just makes legitimate uses for the act a royal pain in the ass. Why do it at all? Often times I will want to add notes to an incoming email, so that it will remain in my records and will be accessibly by searching for the email. Keeping separate notes makes it harder to keep track of things.

Third, Apple provides no way except for a “flag” to tag a message. Eudora allowed you to use up to 14 different colors to mark email as different types; I used this feature all the time. There is no reason for Apple not to make that highly useful feature available, and yet they never do.

And finally, the Mail app does a crappy job of marking mail as “Replied to.” When I give my students a test using a web page form, for example, I get their results by email; I then correct them and send them back. But when I reply to their original emails, sometime Mail stubbornly refuses to mark the message as “replied to.” Most will, but some will not, leaving me wondering later if I really replied to it at all.

It seems that if, while working on a reply, if you do a “Save” or close and later re-open a draft, the original message will not be marked. Worse, Apple does not give you the option of manually marking the message as having been replied to.

One other annoyance is the mail search. Eudora made theirs easy and powerful; Apple’s version is hard to handle. It took me a few years to realize that you could search for more than one keyword or element by using “Smart Mailboxes”–not an intuitive solution at all, nor an easy one to use. Even then, I am deeply dissatisfied with how Apple made it work.

Apple has had more than enough time to perfect their main Mail app, and the iPhone Mail app seems destined for the same fate, with no-brainer features like being able to batch-mark messages as read being left ignored for years.

It is strange that Apple can be so adept at most things, but in a few, isolated but important areas, to do such a poor job. I can only assume that such tasks are split into teams, and some teams are not nearly as good as others.

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  1. Gary
    August 3rd, 2009 at 02:04 | #1

    I am being forced to transition from Eudora (My sweetheart of a mail program) to something else because I have no hair left to pull out when trying the create a satisfactory personality to get mail out through Verizon’s ever-changing authorizations system when visiting my girlfriend’s house. All other ISP, yes; Verizon, no.)

    So, I’m switching to Apple Mail and starting to learn that there are many areas where Apple missed the “intuitive” and logical feature, many of which you mention here.

    One gripe, as I start to learn the new system, is the inability to create a stationery file for newsletter-type sends to different lists. Eudora let me create a virtual letterhead with all the Bcc’s in place and with header and footer links and boilerplate copy, all with one Recipient selection. All that whould be required is to paste the new item in the stationery. So far, I can’t see a way to do this with Mail.

    With Eudora, it wae literally a one-click operation to produce the stationery, ready for pasting-into and sending.

    Being a truly challenged student of any new software (dyslexia + A.D.D.) I’d appreciate hearing of any “…For Dummies” book that can walk me through Apple MAIL, Any suggestions?

    Many thanks

    —Gary

  2. September 28th, 2009 at 03:56 | #2

    I’m with Gary on this one. My biggest issue transitioning from Eudora to Mail is the loss of stationary. I know that Apple Mail on Leopard has a “Stationary” feature, but that’s really a template for how the thing will look. My situation is that I have lots of canned responses for similar questions or issues that happen several times a day. In Eudora, I could simply click on a stationary item and get a fully addressed response ready to go.

    I haven’t figured out how to replicate that in Apple Mail. When I tried to create a special folder — i.e. “Form Letters” — and then copy those into Drafts on an as-needed basis, I ended up sending two versions of the mail.

    Any ideas on how to cobble together something that kind of works?

  3. September 28th, 2009 at 04:21 | #3

    I’ve come up with a work-around which might help someone else who discovers this thread poking around on this issue (like I did).

    Create the form letter email and then save it as a draft. (You may need to open some twiddles to see the draft folder). This can include recipient addresses if you need to send the same letter to the same person once a week, for example — i.e. with a data report or something.

    When you want to send it again, go into the draft folder and select the message, but do not open it. Choose Edit->Copy and then choose Edit->Paste. It should make a duplicate of the letter in the folder. Then open the duplicate, make any changes and send it.

    Not as elegant as Eudora’s solution, but it seems to work.

    Now if I can only get the Apple Mail filters to speak the names of incoming mail from clients, I’ll be set!

  4. Gary
    September 29th, 2009 at 00:09 | #4

    Thanks, Cristoph:

    After reading your post, I’ve tried fiddling with the draft Idea and find it too unforgiving and complex to deal with. (What does “…open some twiddles…” mean? Sounds like a jar of magic pills, or am I missing something).

    Anyway, it’s pretty clear that MAIL, in its present form, will not provide a useful stationery. This kind oversight is uncharacteristic of an Apple program. It makes MAIL only useful for basic beginner letter writing, for the kiddies if you will.

    Even a customizeable art format that allows for a blank page with user added typography and headers and footers would be helpful, if they could be stored and opened for use like stationery.

    Bottom line for me is that it’s easier to deal with the conflicts with Eudora’s use than it is to surrender effective communication with my variety of recipients in order to use Apple’s spartan, unhelpful and labor-intensive (for my needs) program.

    I’ve re-subscribed to the old axiom: If it ain’t broke, don’t fix it.

    I’m staying with Eudora. (We’re having a ceremony this afternoon to re-state our vows to each other. No flowers, please).

    —Gary

  5. October 5th, 2009 at 03:32 | #5

    Hi Gary,

    Actually, I’ve been using the trick of saving the “stationary” in drafts and then copying it when I need it — and it works. (“Twiddles” are just those little disclosure triangles that reveal their contents when clicked upon). Although I made it sound complicated, it’s really just select the message, copy, paste, open and write.

    So I’m a switcher. I agree with your axiom: if it ain’t broke, don’t fix it. But, for me, Eudora was broken. I was increasingly getting open transport errors which required me to quit and restart. Occasionally, Eudora would scramble all the items in my IN box, giving a bunch of duplicates with ??? in one of the columns. Or I would run up against the mailbox message limit. And I couldn’t make sense of incoming HTML email — a scourge, I know, but still sometimes necessary to read. The Eudora “Open in Browser” trick was getting old.

    So I’ve had to give up an old friend and move along — to continue your analogy: dump her for a younger woman. It’s been a better transition than I thought, especially after I found the wonderful and free Eudora Mailbox Cleaner which did a much better job of importing than Apple Mail itself. (Here’s the link: http://homepage.mac.com/aamann/Eudora_Mailbox_Cleaner.html ) I now have all my email going back to 1995 in Apple Mail, and it’s all searchable and accessible. (The search in Apple Mail is even better than Eudora’s — and I always thought that was one of Eudora’s strongest features.)

    So I left Eudora very reluctantly, but it hasn’t been nearly as bad as thought it would be. I do miss the ability to have my incoming email run through a filter which would read aloud the names of messages from clients — but you can’t have everything!

    –Christopher

  6. Stormchild
    May 18th, 2010 at 19:34 | #6

    I agree with you on many of these points — Apple’s Mail app has always been one of those frustratingly bad things they just can’t seem to fix — but I’m surprised you have never discovered the rather obvious “Flag” button for flagging messages (which you claim it doesn’t have). There are multiple ways to set a message as ‘flagged’ in Mail.

    – Use the Flag button in the toolbar (if you don’t see one, right-click anywhere in the toolbar, choose Customize Toolbar, and drag the Flag button somewhere on your toolbar). You’ll find it in the toolbar for the main Mail window, as well as any window for a message you’ve received.

    …or…

    – Right-click a message in the list, and choose Mark > As Flagged. If you have multiple messages selected, they will all be flagged. (Alternatively you can select one or more messages, and choose the same option from the Message menu at the top.)

    Nonetheless I share your (seemingly hopeless) wish for a competent email client from Apple. I wouldn’t hold your breath though. Apple seems more interested in adding silly crap like stationery, notes and to-dos, than fixing the core functionality of the app.

  7. Luis
    May 19th, 2010 at 00:16 | #7

    Storm:

    Gotta read carefully: “Apple provides no way except for a ‘flag’ to tag a message.” I use the flag all the time, but would rather be able to use colors like in Eudora.

    I appreciate the help, though!

  8. Al
    May 28th, 2010 at 01:19 | #8

    @Christopher Werby
    One very clunky way to do it would be to create a number of different signatures, because as far as I know it doesn’t limit you to any certain number of characters. Although I have never tried to do it, so I am not sure it would work.

    My pet peeve is that when I flag something, it only allows me to flag with one color. It seems like it would be a very easy fix for Apple to add a color selection to the flag application.

  9. Anonymous
    May 28th, 2010 at 01:53 | #9

    Hi Al,

    That’s an interesting work-around, but I need them to contain the email addresses of the recipients. I send out weekly and monthly reports to the same group of people, or have a bcc field to a CRM system, and the draft approach helps to avoid errors.

    After spending some time with Apple Mail, I have come to like it. There are some things I miss from Eudora — it was a lot easier to cancel an email mistakenly sent; the filtering was better — but there’s a lot to like about Apple Mail.

    Your signature trick might be just the thing for a customer service rep who has to send the same response over and over during the course of the day. I keep getting those canned responses, so I know they’ve figured out some solution!

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