Why does it take three attempts to send before an email is finally sent?

Just recently, I have experienced that almost every time I try to send an email, I get a dialogue box saying that I should try again later. After two attempts in rapid succession, it finally sends on the third try. Why?

What anti virus? What mail provider?

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It depends on the size of the attachment and the speed of your internet connection.
Next time you send an email with an attachment do these two things:
In Apple Mail (I assume you are using Apple Mail), under the Window menu select Activity. Arrange the Activity window so you can see it.
Then open the separate application located in the Utilities folder called "Activity Monitor" and arrange it so you can see it at the same time as the Activity window in Mail.
In Activity Monitor program, select the tab labeled "Network." Watch the "Data sent/sec" portion. Then send your email, while watching the Mail Activity window and also the Activity Monitor program window Data sent/sec area.
You should see the mail being sent with a progress bar in the Mail Activity window and also you should be able to see how many bytes/sec or KB/sec or MB/sec your internet connection is giving you in the Activity Monitor window.
Example: my internet provider gives me about 20 Megabits per second download and 5 Megabits per second upload. To convert these to Megabytes per second (Activity Monitor shows things in bytes, not bits), simply divide by 10 (not the exact thing to do, but close enough). So I get 0.5 Megabytes per second upload speed. When I send a file that is 5 Megabytes in size, it takes about 10 seconds if I am getting the full upload bandwidth. If I am getting less than that (which sometimes happens), it will take proportionately more time. Either way, you can see what is happening with these two windows.
If your internet provider is supposed to give you, say, 5 Megabits/sec upload (0.5 Megabytes/sec), but you see only say, 5 KB/sec (=0.005 Megabytes/sec), sent in Activity Monitor, then your emails are taking a long time because you are getting only abut 1/100 the speed you should be. You might want to check with your internet provider about that.

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Why does it take three attempts to send before an email is finally sent?

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