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I had originally posted this on the Webapps site from stack exchange, but didn't get any response, so I thought I'd try here as well.

I sent out an email recently that gave the wrong character representations. The email itself is a newsletter sent out through Gmail and the issue doesn't seem to happen too often. The recipient sent me the email he received (he had read it on an iPad).

For example, the following text:

After Sri Lanka’s experiment with protectionism under the Sri Lanka Freedom Party in the 1970s failed, Wickremesinghe’s uncle, former President J.R. Jayawardena, initiated a massive liberalization drive in 1977, following a landslide election victory.

was displayed as:

After Sri Lanka=E2=80=99s experiment with protectionism under the Sri Lanka= Freedom Party in the 1970s failed, Wickremesinghe=E2=80=99s uncle, former President= J.R. Jayawardena, initiated a massive liberalization drive in 1977, following =E2=80=8B=E2=80=8B a landslide election victory.

I should note that the characters are displayed as Sri Lanka=E2=80=99s and not like Sri Lanka=3DE2=3D80=3D99s

The way this mail was done is, first I made the mail on my personal Yahoo account and sent it to a company Gmail account. It was forwarded from the Gmail account to this recipient.

When I checked my sent mail on Yahoo, everything looked fine. However, I noticed that the raw message had this strange formatting everywhere.

I have no idea what could have caused it though. A little googling told me that it might be that Content-Transfer-Encoding is set to quoted-printable. When checking the email headers, it is in fact set to quoted-printable

The rest of the email headers are as follows (sensitive info has been ...-fied):

MIME-Version: 1.0
Received: by 10.200.58.130 with HTTP; Mon, 3 Jul 2017 19:08:12 -0700 (PDT)
Date: Tue, 4 Jul 2017 07:38:12 +0530
Delivered-To: fr...ma@gmail.com
Message-ID: <CABwGrnBtUxcF5gyyW=6DyBy1r6nH3p0QATwFKtVUUs2Jttaoew@mail.gmail.com>
Subject: Second Update - 04.07.2017
From: T... T... <fr...ma@gmail.com>
To: f... <fr...ly@googlegroups.com>
Content-Type: multipart/alternative; boundary="001a11455b06085fd30553745b69"

--001a11455b06085fd30553745b69
Content-Type: text/plain; charset="UTF-8"
Content-Transfer-Encoding: quoted-printable

Any idea what went wrong or how I could fix it?

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    the recipient isn't handling utf-8, or decompression. If viewed on cell phone, most likely decompression issue and needs upgrading. If issue on desktop/laptop, locale not correct. In any event, not your issue. You might be able to choose a font in plain ascii. Oct 6, 2017 at 11:35
  • The apostrophe is idiosyncratic to an application, e.g. MS Office or LibreOffice, that use special characters for open single quotation mark and close single quotation mark. When pasting text meant to be readable on all devices, paste it into Notepad++ or similar text editor, remove any special characters and then transfer it to email. Oct 6, 2017 at 19:31
  • @DrMoishePippik So, does that mean that I'd have to do this with each and every email that I make? Especially, given that I cannot predict when this issue will pop up and that I use MS Word when making most of my email - I use mail merge when making emails. Oct 10, 2017 at 9:35
  • Also, what about the weird formatting in the last sentence of the extract I posted - following =E2=80=8B=E2=80=8B a landslide election victory - that doesn't have a quotation mark or anything, it's simply a space! Oct 10, 2017 at 12:37
  • Take your original message, put it into a text editor such as Notepad or Notepad++, and see what you are actually sending. Mail merge may also be mangling the text, though... it could be sending characters used in formatting (e.g. font name) internal to MS Word. Oct 11, 2017 at 2:03

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