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Old 6 Jun 2022, 02:37 PM   #1
xyzzy
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Need confirmation: sending a pdf as an attachment

As title says, I need confirmation on whether you can attach a pdf to an email and (a) save the email as a draft and if so be able to successfully send it.

Apparently I can't do either! If I construct an email with a pdf I get an error message saying "send failed". If I only try to save the as a draft without even sending the draft isn't saved.

I tried this on both the webmail and the FM app (which I assume is just another webmail interface).

I previously encountered a problem where the FM app wasn't a choice listed in the iPhone transfer function for some (not all) apps (e.g., Safari). I made a ticket on that one. Last ticket update on that one was April 22 telling me they haven't been able to pin that down. I don't consider that very serious and can live without it. But not being able to enclose and send a pdf is a whole different animal. That I think is serious (to me at least).

And oh, by the way. These are small pdf's so I am not exceeding any enclosure size limits.

Let me know what you find. Just create a draft and add a pdf as an enclosure. Close the draft. Is the draft still there? If so try to send it (to yourself is sufficient). Does is send successfully?

Update a little later:
Well it's not as serious as I originally made out. Apparently I can use my Thunderbird email client to send the pdf's so all is not lost after all. This means the problem lies with the webmail interface (I assume the FM app is just another glorified webmail interface).

Also, I submitted a ticket anyhow.

Last edited by xyzzy : 6 Jun 2022 at 03:24 PM.
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Old 6 Jun 2022, 06:11 PM   #2
FredOnline
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I just tried this, created draft with an added PDF attachment, went into inbox to look at another e-mail, went back into drafts, did edit draft, and then sent.

Received OK at destination address.

Using Linux Mint desktop, Firefox browser.
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Old 6 Jun 2022, 06:54 PM   #3
xyzzy
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Hmm, ok. Not sure what's going on with my system then. Thanks for the quick feedback.

Based on what you said I tried using a different version of my Firefox browser (one I keep around with a relatively clean profile). It worked. I guess I didn't try that earlier. But...

Try sending a pdf attachment with the FM app. I still can't get that to work on my iPhone 13pro (using latest iOS 15.5). It demonstrates the same misbehavior as my main FF browser. The difference in tests between the app and using my browser on my computer is that on the computer I simply drag the pdf into the message I'm composing. On the iPhone I used the "attach from file storage" (paper clip) to get to the pdf I previously added to FM Files section. On the app, if I click it's save draft (click the X in upper left) the widow changes to the drafts and I can actually see it add the drafts folder and then it immediately disappears. Whatever is causing it to delete the draft is probably the same thing as causing the send to fail.

If it was just my main browser showing this behavior I wouldn't have been surprised since I use an out of date old version of Firefox with lots of add-on.* Lot's of pages have problems there where using a version with a clean profile it works almost certainly points my usual problems I have with this browser. Nothing new or surprising there. That would be the end of the story if it were not for the fact that I'm seeing the same misbehavior from the iPhone app.

[*I don't want to get into why I still am using an old out-of-date browser]

Last edited by xyzzy : 6 Jun 2022 at 07:46 PM.
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Old 6 Jun 2022, 08:55 PM   #4
BritTim
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As an experiment, see if you can upload a PDF file into your Fastmail Files area. If this works, see if attaching the file from the Files area resolves your problem. If you can get it to the Files area, but still cannot attach it to an email, perhaps you can allow it to be viewable by anyone and send a link in the email rather than a file attachment.

Obviously, this is not a satisfactory long term solution (even if it works) but your immediate priority is surely a workable circumvention.
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Old 6 Jun 2022, 09:21 PM   #5
xyzzy
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Quote:
Originally Posted by BritTim View Post
As an experiment, see if you can upload a PDF file into your Fastmail Files area. If this works, see if attaching the file from the Files area resolves your problem. If you can get it to the Files area, but still cannot attach it to an email, perhaps you can allow it to be viewable by anyone and send a link in the email rather than a file attachment.

Obviously, this is not a satisfactory long term solution (even if it works) but your immediate priority is surely a workable circumvention.
Actually I did upload the pdf's to the FM Files area. That was the only way to create the attachments for the app testing.

FM sent me a reply (sometimes they are fast, sometimes not, maybe I just hit them at a quiet time). Here's what they said:

Quote:
I've checked the logs, and the reason you are seeing this issue is that your computer is sending an invalid content type for the PDF. A PDF should have a content type of "application/pdf" but your computer is sending "application/text-plain:formatted" – the colon there is an invalid character in a content type, causing the creation to be rejected.

It's very odd that you would see this on two different devices, as this is normally a misconfiguration on a single browser or device. Perhaps it's the particular PDF, that's got the wrong type embedded in it somehow?
I am not sure where in my process of creating the pdf's this could happen but it's too late now to test further (4 AM here).
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Old 7 Jun 2022, 07:48 AM   #6
n5bb
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You must have a damaged PDF file. I send PDF (and other file format) attachments using Fastmail (both web and iPhone or iPad apps) all the time without difficulty.

It's easy for me to generate a test PDF. For example, I'm looking at this EMD thread in the Firefox browser. You can use the application menu (hamburger three horizontal line icon) Print feature, and for the print destination choose "save to PDF". There is a similar feature in both the Chrome and Edge browsers. Save the new PDF file in any folder, then choose that file to attached from a Fastmail Compose window. You can either drag the file into the Attach area of the Compose screen, or open the Attach dialog and choose to Upload Files.

It's amazing how well the Fastmail search feature works with attachments. After sending that test email with an attachment of a printout of this thread, I can now do a search in Fastmail for "application/text-plain:formatted" and it immediately finds the email in my Sent box which has that string in the PDF file formed from printing this thread!

Bill
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Old 7 Jun 2022, 04:17 PM   #7
odedp
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Yesterday I've sent a PDF attachment to 40 recipients using the webmail interface (Chrome).
Worked flawlessly
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Old 8 Jun 2022, 07:31 AM   #8
xyzzy
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Quote:
Originally Posted by n5bb View Post
You must have a damaged PDF file. I send PDF (and other file format) attachments using Fastmail (both web and iPhone or iPad apps) all the time without difficulty.

It's easy for me to generate a test PDF. For example, I'm looking at this EMD thread in the Firefox browser. You can use the application menu (hamburger three horizontal line icon) Print feature, and for the print destination choose "save to PDF". There is a similar feature in both the Chrome and Edge browsers. Save the new PDF file in any folder, then choose that file to attached from a Fastmail Compose window. You can either drag the file into the Attach area of the Compose screen, or open the Attach dialog and choose to Upload Files.
My pdf was made from 5 photos I had on my iPhone. I assume the pdf was "damaged" due to the naive method I used to combine the photos on my Mac. I've since leaned of easier and more direct methods to do it all on the iPhone (thanks to some googling). Two examples: combine into a single pdf directly from Photos using it's Print operation, or send to Files from Photos and combine them there (that seemed to make a smaller pdf). Doing it all on the iPhone apparently creates a pdf that FM likes.

Quote:
It's amazing how well the Fastmail search feature works with attachments. After sending that test email with an attachment of a printout of this thread, I can now do a search in Fastmail for "application/text-plain:formatted" and it immediately finds the email in my Sent box which has that string in the PDF file formed from printing this thread!
It found that one? I But the reply from FM tech support I quoted previously said FM was choking on content types with a colon in them.

What search term did you use?

Last edited by xyzzy : 8 Jun 2022 at 07:54 AM.
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Old 8 Jun 2022, 08:27 AM   #9
n5bb
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Quote:
Originally Posted by xyzzy View Post
... It found that one? I But the reply from FM tech support I quoted previously said FM was choking on content types with a colon in them.

What search term did you use?
As I said:
Quote:
I can now do a search in Fastmail for "application/text-plain:formatted".
You used that text string in this thread. So the Fastmail search was discovering those characters embedded inside the PDF file. I was searching for those text characters, not a file type.


Bill
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Old 9 Jun 2022, 01:02 AM   #10
SideshowBob
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Quote:
Originally Posted by xyzzy View Post
"but your computer is sending "application/text-plain:formatted"

I am not sure where in my process of creating the pdf's this could happen but it's too late now to test further (4 AM here).
My understanding is that these days practically everything gets mime-type from the file extension, possibly falling back to traditional UNIX style "magic numbers". I tested this on the Android FM app and webmail (Firefox on Xfce4/FreeBSD) and only the extension mattered. If your files had a ".pdf" extension it's very unlikely that the content made any difference.

My suspicion is that this is a Fastmail bug. If you remove the .pdf extension FM encodes the attachment as "application/octet-stream", the default for an unknown type. I tested the webmail in Xfce which uses freedesktop.org standard mime handling. This does fall back to magic numbers and xdg-mime will identify a renamed file as "application/pdf". On balance it seems most likely that FM does its own file extension to mime mapping. It would make sense to do this for the well-known file extensions.
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