I love the "Send Later" feature. I recently used it to compose
some messages that I later wanted to edit before sending, plus one
that I wanted to send earlier than planned. I found a few things
confusing about the way this works, so I'd like to propose some
improvements.
When editing a normal draft message (not with Send Later), the
user can simply double-click on the message to open it in a compose
window. Upon sending or saving it, the original draft is
automatically deleted so there is no duplicate.
With a draft which is "pending submission" however, this is
completely different. Double-clicking on the message does not open
a compose window at all. Instead, it does a search for similar
messages as if it was not a draft. Selecting "Edit as New Message"
seems to be the logical option here, but then that creates a
duplicate message. In this case, the original unedited message is
also still sent at the previously scheduled time, which could
create an embarrassing situation. After trying these other options,
I realized the proper solution is to select "Cancel Send", which
then automatically opens a compose window. (This popup was a
pleasant but unexpected surprise).
One easy way to make this more intuitive is to change the
command to: Cancel Send and Edit Message (if that isn't too long).
That better describes what it does. Another option is to create a
separate command such as "Edit Draft Message" which does not create
a duplicate message, although that may be the exact same thing as
what "Cancel Send" does now. I'd also suggest this be the default
when double-clicking on a message which is pending submission so
they function similarly to editing any other draft message.
Lastly, it would be very helpful if there are some
context-sensitive buttons added to the GUI to Send Now, Cancel
Send, Edit, etc. In particular, users shouldn't have to know to
press the Control key to find the Send Now feature, as that is
likely to be needed fairly often.
Thanks for considering these improvements!