senorblanco@: I did bisect, it eventually points to this CL:
https://codereview.chromium.org/1530503004

I tried revert that CL locally, and this problem goes away. Could you take a look and provide some insights?

 Issue 603727  has been merged into this issue.

Looks like it's a Skia bug. I'll take this on.

Part of the failure (as an impl detail) is that we are not applying the ctm to the canvas context, but adding it to the imagefilter dag directly. If it were on the context (canvas), the blur would show (though only correctly for sigmas where X == Y)

I don't think that's the problem. The matrix applied to the SkLocalMatrixImageFilter is supposed to be the inverse of the CTM at canvas draw time. The regular CTM is already in the SkCanvas's CTM. That way, the shadow stays at a fixed offset, regardless of the CTM (canvas semantics), but the
primitive is still drawn transformed.

The following revision refers to this bug:
  https://chromium.googlesource.com/chromium/src.git/+/d21fd4984450f9b8cca710bf76a05beec62e243a

commit d21fd4984450f9b8cca710bf76a05beec62e243a
Author: senorblanco <senorblanco@chromium.org>
Date: Tue Apr 19 19:25:20 2016

Revert "2D canvas: pass unmodified primitive bounds to saveLayer()."

This is a manual revert, since Skia has changed in the meantime
(e.g., no longer requires filtered bounds to be passed to
saveLayer()).

R=junov@chromium.org

BUG= 602933 

Review URL: https://codereview.chromium.org/1900523003

Cr-Commit-Position: refs/heads/master@{#388272}

[modify] https://crrev.com/d21fd4984450f9b8cca710bf76a05beec62e243a/third_party/WebKit/LayoutTests/TestExpectations
[modify] https://crrev.com/d21fd4984450f9b8cca710bf76a05beec62e243a/third_party/WebKit/Source/modules/canvas2d/BaseRenderingContext2D.cpp

The following revision refers to this bug:
  https://chromium.googlesource.com/chromium/src.git/+/ca7eabfe2b7031f913abd478f788e105a792585e

commit ca7eabfe2b7031f913abd478f788e105a792585e
Author: Rebaseline Bot <blink-rebaseline-bot@chromium.org>
Date: Fri May 06 19:37:38 2016

Auto-rebaseline for r392107

https://chromium.googlesource.com/chromium/src/+/8496f370f

BUG= 602785 , 602933 , 605515 
TBR=senorblanco@chromium.org

Review URL: https://codereview.chromium.org/1959753002 .

Cr-Commit-Position: refs/heads/master@{#392127}

[modify] https://crrev.com/ca7eabfe2b7031f913abd478f788e105a792585e/third_party/WebKit/LayoutTests/TestExpectations
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[modify] https://crrev.com/ca7eabfe2b7031f913abd478f788e105a792585e/third_party/WebKit/LayoutTests/platform/linux/svg/batik/filters/feTile-expected.png
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[modify] https://crrev.com/ca7eabfe2b7031f913abd478f788e105a792585e/third_party/WebKit/LayoutTests/platform/mac/svg/batik/filters/feTile-expected.png
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[modify] https://crrev.com/ca7eabfe2b7031f913abd478f788e105a792585e/third_party/WebKit/LayoutTests/platform/win/svg/batik/filters/feTile-expected.png
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The bug appear again. I do not know if is cause by something new or is the same thing, but again images on rotated canvas context have no shadow on chrome latest version 50.0.2661.102

The following revision refers to this bug:
  https://chromium.googlesource.com/chromium/src.git/+/50e642f1865e4d09195bcee228f56478ea3e8364

commit 50e642f1865e4d09195bcee228f56478ea3e8364
Author: wangxianzhu <wangxianzhu@chromium.org>
Date: Wed Jun 01 20:06:43 2016

Rebaseline forced ManualNeedsRebaselines during auto-rebaseline problem

BUG= 604144 , 396825 , 607185 , 587094 , 155836 , 602933 
TBR=wkorman@chromium.org

Review-Url: https://codereview.chromium.org/2025243002
Cr-Commit-Position: refs/heads/master@{#397217}

[modify] https://crrev.com/50e642f1865e4d09195bcee228f56478ea3e8364/third_party/WebKit/LayoutTests/TestExpectations
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[modify] https://crrev.com/50e642f1865e4d09195bcee228f56478ea3e8364/third_party/WebKit/LayoutTests/platform/linux/fast/repaint/outline-change-invalidation-expected.txt
[modify] https://crrev.com/50e642f1865e4d09195bcee228f56478ea3e8364/third_party/WebKit/LayoutTests/platform/linux/fast/repaint/outline-clip-change-expected.txt
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[add] https://crrev.com/50e642f1865e4d09195bcee228f56478ea3e8364/third_party/WebKit/LayoutTests/platform/mac-mac10.10/fast/text/complex-text-opacity-expected.png
[add] https://crrev.com/50e642f1865e4d09195bcee228f56478ea3e8364/third_party/WebKit/LayoutTests/platform/mac-mac10.10/fast/text/ellipsis-ltr-text-in-ltr-flow-expected.png
[add] https://crrev.com/50e642f1865e4d09195bcee228f56478ea3e8364/third_party/WebKit/LayoutTests/platform/mac-mac10.10/fast/text/ellipsis-ltr-text-in-rtl-flow-expected.png
[add] https://crrev.com/50e642f1865e4d09195bcee228f56478ea3e8364/third_party/WebKit/LayoutTests/platform/mac-mac10.10/fast/text/ellipsis-rtl-text-in-ltr-flow-expected.png
[add] https://crrev.com/50e642f1865e4d09195bcee228f56478ea3e8364/third_party/WebKit/LayoutTests/platform/mac-mac10.10/fast/text/ellipsis-rtl-text-in-rtl-flow-expected.png
[add] https://crrev.com/50e642f1865e4d09195bcee228f56478ea3e8364/third_party/WebKit/LayoutTests/platform/mac-mac10.10/fast/text/fallback-traits-fixup-expected.png
[add] https://crrev.com/50e642f1865e4d09195bcee228f56478ea3e8364/third_party/WebKit/LayoutTests/platform/mac-mac10.10/transforms/2d/hindi-rotated-expected.png
[modify] https://crrev.com/50e642f1865e4d09195bcee228f56478ea3e8364/third_party/WebKit/LayoutTests/platform/mac-mac10.9/fast/text/complex-text-opacity-expected.png
[add] https://crrev.com/50e642f1865e4d09195bcee228f56478ea3e8364/third_party/WebKit/LayoutTests/platform/mac-mac10.9/fast/text/complex-text-opacity-expected.txt
[add] https://crrev.com/50e642f1865e4d09195bcee228f56478ea3e8364/third_party/WebKit/LayoutTests/platform/mac-mac10.9/fast/text/ellipsis-ltr-text-in-ltr-flow-expected.png
[add] https://crrev.com/50e642f1865e4d09195bcee228f56478ea3e8364/third_party/WebKit/LayoutTests/platform/mac-mac10.9/fast/text/ellipsis-ltr-text-in-rtl-flow-expected.png
[add] https://crrev.com/50e642f1865e4d09195bcee228f56478ea3e8364/third_party/WebKit/LayoutTests/platform/mac-mac10.9/fast/text/ellipsis-rtl-text-in-ltr-flow-expected.png
[add] https://crrev.com/50e642f1865e4d09195bcee228f56478ea3e8364/third_party/WebKit/LayoutTests/platform/mac-mac10.9/fast/text/ellipsis-rtl-text-in-rtl-flow-expected.png
[modify] https://crrev.com/50e642f1865e4d09195bcee228f56478ea3e8364/third_party/WebKit/LayoutTests/platform/mac-mac10.9/fast/text/fallback-traits-fixup-expected.png
[add] https://crrev.com/50e642f1865e4d09195bcee228f56478ea3e8364/third_party/WebKit/LayoutTests/platform/mac-mac10.9/fast/text/font-features/caps-native-synthesis-expected.png
[modify] https://crrev.com/50e642f1865e4d09195bcee228f56478ea3e8364/third_party/WebKit/LayoutTests/platform/mac-mac10.9/transforms/2d/hindi-rotated-expected.png
[modify] https://crrev.com/50e642f1865e4d09195bcee228f56478ea3e8364/third_party/WebKit/LayoutTests/platform/mac-mac10.9/transforms/2d/hindi-rotated-expected.txt
[delete] https://crrev.com/c6de0f49ae06fd3a2f2459e7161f26c4673c10d0/third_party/WebKit/LayoutTests/platform/mac/css3/masking/clip-path-polygon-evenodd-expected.png
[delete] https://crrev.com/c6de0f49ae06fd3a2f2459e7161f26c4673c10d0/third_party/WebKit/LayoutTests/platform/mac/css3/masking/clip-path-polygon-expected.png
[delete] https://crrev.com/c6de0f49ae06fd3a2f2459e7161f26c4673c10d0/third_party/WebKit/LayoutTests/platform/mac/css3/masking/clip-path-polygon-nonzero-expected.png
[delete] https://crrev.com/c6de0f49ae06fd3a2f2459e7161f26c4673c10d0/third_party/WebKit/LayoutTests/platform/mac/fast/backgrounds/transformed-body-background-expected.png
[delete] https://crrev.com/c6de0f49ae06fd3a2f2459e7161f26c4673c10d0/third_party/WebKit/LayoutTests/platform/mac/fast/backgrounds/transformed-body-html-background-expected.png
[modify] https://crrev.com/50e642f1865e4d09195bcee228f56478ea3e8364/third_party/WebKit/LayoutTests/platform/mac/fast/css/text-overflow-ellipsis-bidi-expected.png
[modify] https://crrev.com/50e642f1865e4d09195bcee228f56478ea3e8364/third_party/WebKit/LayoutTests/platform/mac/fast/css/text-overflow-ellipsis-expected.png
[modify] https://crrev.com/50e642f1865e4d09195bcee228f56478ea3e8364/third_party/WebKit/LayoutTests/platform/mac/fast/css/text-overflow-ellipsis-strict-expected.png
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[add] https://crrev.com/50e642f1865e4d09195bcee228f56478ea3e8364/third_party/WebKit/LayoutTests/platform/mac/fast/text/ellipsis-ltr-text-in-ltr-flow-expected.txt
[add] https://crrev.com/50e642f1865e4d09195bcee228f56478ea3e8364/third_party/WebKit/LayoutTests/platform/mac/fast/text/ellipsis-ltr-text-in-rtl-flow-expected.png
[add] https://crrev.com/50e642f1865e4d09195bcee228f56478ea3e8364/third_party/WebKit/LayoutTests/platform/mac/fast/text/ellipsis-ltr-text-in-rtl-flow-expected.txt
[add] https://crrev.com/50e642f1865e4d09195bcee228f56478ea3e8364/third_party/WebKit/LayoutTests/platform/mac/fast/text/ellipsis-rtl-text-in-ltr-flow-expected.png
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[modify] https://crrev.com/50e642f1865e4d09195bcee228f56478ea3e8364/third_party/WebKit/LayoutTests/platform/mac/svg/transforms/svg-css-transforms-expected.txt
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I ran into the same issue and going back to the jsfiddle, this issue has regressed. I'm on chrome 51.0.2704

Hi maddalab, could you please try canary: https://www.google.com/chrome/browser/canary.html

I tested, and this bug happens on stable (51), but fixed on canary. I guess the fix by senorblanco@ as pushed in after 51.0.2704.

Verified on Canary - Version 54.0.2791.0 canary (64-bit).

Confirming issue has been fixed and working as expected. 

As M52 no in stable, this bug is outdated. Closing this now.