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.

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 with HTTP; Mon, 3 Jul 2017 19:08:12 -0700 (PDT) Date: Tue, 4 Jul 2017 07:38:12 +0530 Delivered-To: [email protected] Message-ID: <CABwGrnBtUxcF5gyyW=6DyBy1r6nH3p0QATwFKtVUUs2Jttaoew@mail.gmail.com> Subject: Second Update - 04.07.2017 From: T... T... <[email protected]> To: f... <[email protected]> Content-Type: multipart/alternative; boundary="001a11455b06085fd30553745b69"

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

  • This seems like an iPad issue with encoding, and nothing to do with using a web app.
    – ale
    Sep 3, 2019 at 19:21

1 Answer 1


In your example text you use a typographic apostrophe, the one with a bit of a curve.

You should be using a typewriter apostrophe which is a bit more straight looking.


As you noticed with the Content-Transfer-Encoding value, this happens when a special character that cannot be encoded using 7-bit encoding is used and therefore enforces quoted-printable encoding.

Every email client will have different capabilities in what I can display and how. You essentially have to build for the lowest common denominator.

More can be read on the RFC1341 spec for Content-Transfer-Encoding

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