diff --git a/docker/skia-build-tools/Dockerfile b/docker/skia-build-tools/Dockerfile
index 085095a317..e081f37bfa 100644
--- a/docker/skia-build-tools/Dockerfile
+++ b/docker/skia-build-tools/Dockerfile
@@ -11,6 +11,7 @@ RUN apt-get update && apt-get upgrade -y && apt-get install -y \
   && groupadd -g 2000 skia \
   && useradd -u 2000 -g 2000 skia
 
+# TODO(kjlubick): Try a shallow clone of depot_tools
 RUN cd /tmp \
   && git clone 'https://chromium.googlesource.com/chromium/tools/depot_tools.git'
 
diff --git a/infra/bots/recipe_modules/build/canvaskit.py b/infra/bots/recipe_modules/build/canvaskit.py
index 0a8f1867e4..d04b03b532 100644
--- a/infra/bots/recipe_modules/build/canvaskit.py
+++ b/infra/bots/recipe_modules/build/canvaskit.py
@@ -2,7 +2,7 @@
 # Use of this source code is governed by a BSD-style license that can be
 # found in the LICENSE file.
 
-DOCKER_IMAGE = 'gcr.io/skia-public/canvaskit-emsdk:1.38.47_v1'
+DOCKER_IMAGE = 'gcr.io/skia-public/canvaskit-emsdk:1.39.6_v1'
 INNER_BUILD_SCRIPT = '/SRC/skia/infra/canvaskit/build_canvaskit.sh'
 
 
diff --git a/infra/bots/recipe_modules/build/examples/full.expected/Build-Debian9-EMCC-asmjs-Debug-PathKit.json b/infra/bots/recipe_modules/build/examples/full.expected/Build-Debian9-EMCC-asmjs-Debug-PathKit.json
index 261f879457..b5a713637d 100644
--- a/infra/bots/recipe_modules/build/examples/full.expected/Build-Debian9-EMCC-asmjs-Debug-PathKit.json
+++ b/infra/bots/recipe_modules/build/examples/full.expected/Build-Debian9-EMCC-asmjs-Debug-PathKit.json
@@ -23,7 +23,7 @@
       "[START_DIR]/cache/work:/SRC",
       "--volume",
       "[START_DIR]/cache/docker/pathkit:/OUT",
-      "gcr.io/skia-public/emsdk-base:1.38.47_v1",
+      "gcr.io/skia-public/emsdk-base:1.39.6_v1",
       "/SRC/skia/infra/pathkit/build_pathkit.sh",
       "debug",
       "asm.js"
diff --git a/infra/bots/recipe_modules/build/examples/full.expected/Build-Debian9-EMCC-asmjs-Release-PathKit.json b/infra/bots/recipe_modules/build/examples/full.expected/Build-Debian9-EMCC-asmjs-Release-PathKit.json
index f02b19320d..b4afc8d802 100644
--- a/infra/bots/recipe_modules/build/examples/full.expected/Build-Debian9-EMCC-asmjs-Release-PathKit.json
+++ b/infra/bots/recipe_modules/build/examples/full.expected/Build-Debian9-EMCC-asmjs-Release-PathKit.json
@@ -23,7 +23,7 @@
       "[START_DIR]/cache/work:/SRC",
       "--volume",
       "[START_DIR]/cache/docker/pathkit:/OUT",
-      "gcr.io/skia-public/emsdk-base:1.38.47_v1",
+      "gcr.io/skia-public/emsdk-base:1.39.6_v1",
       "/SRC/skia/infra/pathkit/build_pathkit.sh",
       "asm.js"
     ],
diff --git a/infra/bots/recipe_modules/build/examples/full.expected/Build-Debian9-EMCC-wasm-Debug-CanvasKit.json b/infra/bots/recipe_modules/build/examples/full.expected/Build-Debian9-EMCC-wasm-Debug-CanvasKit.json
index 99b6feaea3..69b66f56ae 100644
--- a/infra/bots/recipe_modules/build/examples/full.expected/Build-Debian9-EMCC-wasm-Debug-CanvasKit.json
+++ b/infra/bots/recipe_modules/build/examples/full.expected/Build-Debian9-EMCC-wasm-Debug-CanvasKit.json
@@ -23,7 +23,7 @@
       "[START_DIR]/cache/work:/SRC",
       "--volume",
       "[START_DIR]/cache/docker/canvaskit:/OUT",
-      "gcr.io/skia-public/canvaskit-emsdk:1.38.47_v1",
+      "gcr.io/skia-public/canvaskit-emsdk:1.39.6_v1",
       "/SRC/skia/infra/canvaskit/build_canvaskit.sh",
       "debug"
     ],
diff --git a/infra/bots/recipe_modules/build/examples/full.expected/Build-Debian9-EMCC-wasm-Debug-PathKit.json b/infra/bots/recipe_modules/build/examples/full.expected/Build-Debian9-EMCC-wasm-Debug-PathKit.json
index 432e6e7f5c..12b0ceaed7 100644
--- a/infra/bots/recipe_modules/build/examples/full.expected/Build-Debian9-EMCC-wasm-Debug-PathKit.json
+++ b/infra/bots/recipe_modules/build/examples/full.expected/Build-Debian9-EMCC-wasm-Debug-PathKit.json
@@ -23,7 +23,7 @@
       "[START_DIR]/cache/work:/SRC",
       "--volume",
       "[START_DIR]/cache/docker/pathkit:/OUT",
-      "gcr.io/skia-public/emsdk-base:1.38.47_v1",
+      "gcr.io/skia-public/emsdk-base:1.39.6_v1",
       "/SRC/skia/infra/pathkit/build_pathkit.sh",
       "debug"
     ],
diff --git a/infra/bots/recipe_modules/build/examples/full.expected/Build-Debian9-EMCC-wasm-Release-CanvasKit_CPU.json b/infra/bots/recipe_modules/build/examples/full.expected/Build-Debian9-EMCC-wasm-Release-CanvasKit_CPU.json
index 29e50b5c19..ca8510c35d 100644
--- a/infra/bots/recipe_modules/build/examples/full.expected/Build-Debian9-EMCC-wasm-Release-CanvasKit_CPU.json
+++ b/infra/bots/recipe_modules/build/examples/full.expected/Build-Debian9-EMCC-wasm-Release-CanvasKit_CPU.json
@@ -23,7 +23,7 @@
       "[START_DIR]/cache/work:/SRC",
       "--volume",
       "[START_DIR]/cache/docker/canvaskit:/OUT",
-      "gcr.io/skia-public/canvaskit-emsdk:1.38.47_v1",
+      "gcr.io/skia-public/canvaskit-emsdk:1.39.6_v1",
       "/SRC/skia/infra/canvaskit/build_canvaskit.sh",
       "cpu"
     ],
diff --git a/infra/bots/recipe_modules/build/examples/full.expected/Build-Debian9-EMCC-wasm-Release-PathKit.json b/infra/bots/recipe_modules/build/examples/full.expected/Build-Debian9-EMCC-wasm-Release-PathKit.json
index b9c007172a..aec107dd13 100644
--- a/infra/bots/recipe_modules/build/examples/full.expected/Build-Debian9-EMCC-wasm-Release-PathKit.json
+++ b/infra/bots/recipe_modules/build/examples/full.expected/Build-Debian9-EMCC-wasm-Release-PathKit.json
@@ -23,7 +23,7 @@
       "[START_DIR]/cache/work:/SRC",
       "--volume",
       "[START_DIR]/cache/docker/pathkit:/OUT",
-      "gcr.io/skia-public/emsdk-base:1.38.47_v1",
+      "gcr.io/skia-public/emsdk-base:1.39.6_v1",
       "/SRC/skia/infra/pathkit/build_pathkit.sh"
     ],
     "env": {
diff --git a/infra/bots/recipe_modules/build/pathkit.py b/infra/bots/recipe_modules/build/pathkit.py
index 01acae8dad..82dbca3749 100644
--- a/infra/bots/recipe_modules/build/pathkit.py
+++ b/infra/bots/recipe_modules/build/pathkit.py
@@ -2,7 +2,7 @@
 # Use of this source code is governed by a BSD-style license that can be
 # found in the LICENSE file.
 
-DOCKER_IMAGE = 'gcr.io/skia-public/emsdk-base:1.38.47_v1'
+DOCKER_IMAGE = 'gcr.io/skia-public/emsdk-base:1.39.6_v1'
 INNER_BUILD_SCRIPT = '/SRC/skia/infra/pathkit/build_pathkit.sh'
 
 def compile_fn(api, checkout_root, _ignore):
diff --git a/infra/canvaskit/build_canvaskit.sh b/infra/canvaskit/build_canvaskit.sh
index c7daddecd9..fffc6653b9 100755
--- a/infra/canvaskit/build_canvaskit.sh
+++ b/infra/canvaskit/build_canvaskit.sh
@@ -9,7 +9,7 @@
 # is mounted at /OUT
 
 # For example:
-# docker run -v $SKIA_ROOT:/SRC -v $SKIA_ROOT/out/canvaskit:/OUT gcr.io/skia-public/emsdk-base:1.38.47_v1 /SRC/infra/canvaskit/build_canvaskit.sh
+# docker run -v $SKIA_ROOT:/SRC -v $SKIA_ROOT/out/canvaskit:/OUT gcr.io/skia-public/emsdk-base:1.39.6_v1 /SRC/infra/canvaskit/build_canvaskit.sh
 
 set +e
 set -x
diff --git a/infra/canvaskit/docker/Makefile b/infra/canvaskit/docker/Makefile
index 453230e86f..e5a2bfae6a 100644
--- a/infra/canvaskit/docker/Makefile
+++ b/infra/canvaskit/docker/Makefile
@@ -1,4 +1,4 @@
-EMSDK_VERSION=1.38.47_v1
+EMSDK_VERSION=1.39.6_v1
 
 publish_canvaskit_emsdk:
 	docker build -t canvaskit-emsdk ./canvaskit-emsdk/
diff --git a/infra/canvaskit/docker/canvaskit-emsdk/Dockerfile b/infra/canvaskit/docker/canvaskit-emsdk/Dockerfile
index 6abd49f4f8..27658f4c9c 100644
--- a/infra/canvaskit/docker/canvaskit-emsdk/Dockerfile
+++ b/infra/canvaskit/docker/canvaskit-emsdk/Dockerfile
@@ -1,7 +1,7 @@
 # A Docker image that augments the Emscripten SDK Docker image
 # with anything needed to build Canvaskit
 
-FROM gcr.io/skia-public/emsdk-base:1.38.47_v1
+FROM gcr.io/skia-public/emsdk-base:1.39.6_v1
 
 RUN apt-get update && apt-get upgrade -y && apt-get install -y \
   libfreetype6-dev
\ No newline at end of file
diff --git a/infra/pathkit/build_pathkit.sh b/infra/pathkit/build_pathkit.sh
index ad9ee730c2..b644f2cc15 100755
--- a/infra/pathkit/build_pathkit.sh
+++ b/infra/pathkit/build_pathkit.sh
@@ -9,7 +9,7 @@
 # is mounted at /OUT
 
 # For example:
-# docker run -v $SKIA_ROOT:/SRC -v $SKIA_ROOT/out/dockerpathkit:/OUT gcr.io/skia-public/emsdk-base:1.38.47_v1 /SRC/infra/pathkit/build_pathkit.sh
+# docker run -v $SKIA_ROOT:/SRC -v $SKIA_ROOT/out/dockerpathkit:/OUT gcr.io/skia-public/emsdk-base:1.39.6_v1 /SRC/infra/pathkit/build_pathkit.sh
 
 set +e
 set -x
diff --git a/infra/wasm-common/docker/Makefile b/infra/wasm-common/docker/Makefile
index 4f75f21017..d47d2c6efc 100644
--- a/infra/wasm-common/docker/Makefile
+++ b/infra/wasm-common/docker/Makefile
@@ -1,4 +1,4 @@
-EMSDK_VERSION=1.38.47_v1
+EMSDK_VERSION=1.39.6_v1
 
 # Can check CHROME_VERSION with
 # docker run karma-chrome-tests /usr/bin/google-chrome-stable --version
diff --git a/infra/wasm-common/docker/emsdk-base/Dockerfile b/infra/wasm-common/docker/emsdk-base/Dockerfile
index e0e9a7a8fa..27c0829796 100644
--- a/infra/wasm-common/docker/emsdk-base/Dockerfile
+++ b/infra/wasm-common/docker/emsdk-base/Dockerfile
@@ -1,11 +1,14 @@
 # A Docker image that has the Emscripten SDK installed to /opt/emsdk
 # Use this image to compile C/C++ code to WASM.
+# It has the Java Runtime to allow the use of the Closure JS compiler/minifier.
+# TODO(kjlubick): add an ARG to make it easier to pass in the version number.
 
 FROM gcr.io/skia-public/skia-build-tools:latest
 RUN apt-get update && apt-get upgrade -y && apt-get install -y \
   nodejs \
   default-jre
 
+# TODO(kjlubick): Try a shallow clone
 RUN cd /opt \
   && git clone https://github.com/emscripten-core/emsdk.git
 
@@ -13,9 +16,9 @@ WORKDIR /opt/emsdk
 
 RUN ./emsdk update-tags
 
-RUN ./emsdk install sdk-1.38.47-64bit
+RUN ./emsdk install sdk-1.39.6-64bit
 
-RUN ./emsdk activate sdk-1.38.47-64bit
+RUN ./emsdk activate sdk-1.39.6-64bit
 
 RUN /bin/bash -c "source ./emsdk_env.sh"
 
diff --git a/modules/canvaskit/CHANGELOG.md b/modules/canvaskit/CHANGELOG.md
index a7f446f787..d84035c5b8 100644
--- a/modules/canvaskit/CHANGELOG.md
+++ b/modules/canvaskit/CHANGELOG.md
@@ -9,6 +9,9 @@ and this project adheres to [Semantic Versioning](https://semver.org/spec/v2.0.0
  - `SkSurface.drawOnce` for drawing a single frame (in addition to already existing
    `SkSurface.requestAnimationFrame` for animation logic).
 
+### Changed
+ - We now compile/ship with Emscripten v1.39.6.
+
 ## [0.12.0] - 2020-01-22
 
 ### Added
diff --git a/modules/canvaskit/Makefile b/modules/canvaskit/Makefile
index 4202004ecb..4159969b73 100644
--- a/modules/canvaskit/Makefile
+++ b/modules/canvaskit/Makefile
@@ -72,5 +72,5 @@ docker-compile:
 	mkdir -p ${SKIA_ROOT}/out/canvaskit_wasm_docker
 	docker run --rm --volume ${SKIA_ROOT}:/SRC \
                --volume ${SKIA_ROOT}/out/canvaskit_wasm_docker:/OUT \
-               gcr.io/skia-public/canvaskit-emsdk:1.38.27_v1 \
+               gcr.io/skia-public/canvaskit-emsdk:1.39.6_v1 \
                /SRC/infra/canvaskit/build_canvaskit.sh
diff --git a/modules/canvaskit/README.md b/modules/canvaskit/README.md
index f260b71183..32e5e1097d 100644
--- a/modules/canvaskit/README.md
+++ b/modules/canvaskit/README.md
@@ -7,7 +7,7 @@ compilation.
 # Compile and Test Locally
 
 ```
-make release
+make release  # make debug is much faster and has better error messages
 make local-example
 ```
 
@@ -24,3 +24,41 @@ any of the "extras", one might run:
 Such a stripped-down version is about half the size of the default release build.
 
 [1]: https://emscripten.org/docs/getting_started/downloads.html
+
+
+# Infrastructure Playbook
+
+When dealing with CanvasKit (or PathKit) on our bots, we use Docker. Check out
+$SKIA_ROOT/infra/wasm-common/docker/README.md for more on building/editing the
+images used for building and testing.
+
+## Updating the version of Emscripten we build/test with
+
+This presumes you have updated emscripten locally to a newer version of the
+sdk and verified/fixed any build issues that have arisen.
+
+  1. Edit `$SKIA_ROOT/infra/wasm-common/docker/emsdk-base/Dockerfile` to install
+     and activate the desired version of Emscripten.
+  2. Edit `$SKIA_ROOT/infra/wasm-common/docker/Makefile` to have `EMSDK_VERSION` be
+     set to that desired version. If there is a suffix that is not `_v1`, reset
+     it to be `_v1`. If testing the image later does not work and edits are made
+     to the emsdk-base Dockerfile to correct that, increment to `_v2`,`_v3`, etc
+     to force the bots to pick up the new image.
+  3. In `$SKIA_ROOT/infra/wasm-common/docker/`, run `make publish_emsdk_base`
+  4. Edit `$SKIA_ROOT/infra/canvaskit/docker/canvaskit-emsdk/Dockerfile` to be based
+     off the new version from step 2. CanvasKit has its own docker image because
+     it needs a few extra dependencies to build with font support.
+  5. Edit `$SKIA_ROOT/infra/canvaskit/docker/Makefile` to have the same version
+     from step 2. It's easiest to keep the `emsdk-base` and `canvaskit-emsdk` versions
+     be in lock-step.
+  6. In `$SKIA_ROOT/infra/canvaskit/docker/`, make `publish_canvaskit_emsdk`.
+  7. In `$SKIA_ROOT/infra/bots/recipe_modules/build/`, update `canvaskit.py`
+     and `pathkit.py` to have `DOCKER_IMAAGE` point to the desired tagged Docker
+     containers from steps 2 and 5 (which should be the same).
+  9. In `$SKIA_ROOT/infra/bots/`, run `make train` to re-train the recipes.
+  10. Optional: Run something like `git grep 1\\.38\\.` in `$SKIA_ROOT` to see if
+     there are any other references that need updating.
+  11. Upload a CL with all the changes. Run all Test.+CanvasKit, Perf.+CanvasKit,
+      Test.+PathKit, Perf.+PathKit jobs to make sure the new builds pass all
+      tests and don't crash the perf harnesses.
+  12. Send out CL for review. Feel free to point the reviewer at these steps.
\ No newline at end of file
diff --git a/modules/canvaskit/compile.sh b/modules/canvaskit/compile.sh
index 3dd6c3c793..fe8a660ca8 100755
--- a/modules/canvaskit/compile.sh
+++ b/modules/canvaskit/compile.sh
@@ -212,9 +212,10 @@ echo "Compiling bitcode"
   cxx=\"${EMCXX}\" \
   ar=\"${EMAR}\" \
   extra_cflags_cc=[\"-frtti\"] \
-  extra_cflags=[\"-s\", \"WARN_UNALIGNED=1\",
+  extra_cflags=[\"-s\", \"WARN_UNALIGNED=1\", \"-s\", \"MAIN_MODULE=1\",
     \"-DSKNX_NO_SIMD\", \"-DSK_DISABLE_AAA\",
     \"-DSK_DISABLE_EFFECT_DESERIALIZATION\",
+    \"-DSK_FORCE_8_BYTE_ALIGNMENT\",
     ${GN_GPU_FLAGS}
     ${GN_SKP_FLAGS}
     ${EXTRA_CFLAGS}
@@ -275,12 +276,13 @@ ${EMCXX} \
     -Ithird_party/skcms \
     -Ithird_party/externals/icu/source/common/ \
     -DSK_DISABLE_AAA \
+    -DSK_FORCE_8_BYTE_ALIGNMENT \
     $WASM_GPU \
     $WASM_PATHOPS \
     $WASM_RT_SHADER \
     $WASM_SKP \
     $FONT_CFLAGS \
-    -std=c++14 \
+    -std=c++17 \
     --bind \
     --pre-js $BASE_DIR/preamble.js \
     --pre-js $BASE_DIR/helper.js \
diff --git a/modules/pathkit/CHANGELOG.md b/modules/pathkit/CHANGELOG.md
index 9a9ff50e3e..dc0b62811c 100644
--- a/modules/pathkit/CHANGELOG.md
+++ b/modules/pathkit/CHANGELOG.md
@@ -7,7 +7,7 @@ and this project adheres to [Semantic Versioning](https://semver.org/spec/v2.0.0
 ## [Unreleased]
 
 ### Changed
- - Updated to emscripten 1.38.47
+ - Updated to emscripten 1.39.6
 
 ## [0.6.0] 2019-02-25
 
diff --git a/modules/pathkit/compile.sh b/modules/pathkit/compile.sh
index 9f1bdbb6a8..fbf8aa0751 100755
--- a/modules/pathkit/compile.sh
+++ b/modules/pathkit/compile.sh
@@ -10,6 +10,9 @@ BASE_DIR=`cd $(dirname ${BASH_SOURCE[0]}) && pwd`
 HTML_SHELL=$BASE_DIR/shell.html
 BUILD_DIR=${BUILD_DIR:="out/pathkit"}
 mkdir -p $BUILD_DIR
+# sometimes the .a files keep old symbols around - cleaning them out makes sure
+# we get a fresh build.
+rm -f $BUILD_DIR/*.a
 
 # This expects the environment variable EMSDK to be set
 if [[ ! -d $EMSDK ]]; then
@@ -73,7 +76,7 @@ OUTPUT="-o $BUILD_DIR/pathkit.js"
 source $EMSDK/emsdk_env.sh
 EMCC=`which emcc`
 EMCXX=`which em++`
-
+EMAR=`which emar`
 
 # Turn off exiting while we check for ninja (which may not be on PATH)
 set +e
@@ -91,7 +94,9 @@ echo "Compiling bitcode"
 ./bin/gn gen ${BUILD_DIR} \
   --args="cc=\"${EMCC}\" \
   cxx=\"${EMCXX}\" \
+  ar=\"${EMAR}\" \
   extra_cflags=[\"-DSK_DISABLE_READBUFFER=1\",\"-s\", \"WARN_UNALIGNED=1\",
+    \"-s\", \"MAIN_MODULE=1\",
     ${EXTRA_CFLAGS}
   ] \
   is_debug=false \
@@ -104,10 +109,8 @@ ${NINJA} -C ${BUILD_DIR} libpathkit.a
 
 echo "Generating WASM"
 
-${EMCXX} $RELEASE_CONF -std=c++14 \
+${EMCXX} $RELEASE_CONF -std=c++17 \
 -I. \
--Ithird_party/skcms \
--std=c++14 \
 --bind \
 --pre-js $BASE_DIR/helper.js \
 --pre-js $BASE_DIR/chaining.js \
diff --git a/src/gpu/GrMemoryPool.h b/src/gpu/GrMemoryPool.h
index 5e063e4da6..e487b04d4e 100644
--- a/src/gpu/GrMemoryPool.h
+++ b/src/gpu/GrMemoryPool.h
@@ -26,8 +26,17 @@
  */
 class GrMemoryPool {
 public:
+#ifdef SK_FORCE_8_BYTE_ALIGNMENT
+    // This is an issue for WASM builds using emscripten, which had
+    // std::max_align_t = 16, but was returning pointers only aligned to 8
+    // bytes. https://github.com/emscripten-core/emscripten/issues/10072
+    // Since Skia does not use "long double" (16 bytes), we should be ok to
+    // force it back to 8 bytes until emscripten is fixed.
+    static constexpr size_t kAlignment = 8;
+#else
     // Guaranteed alignment of pointer returned by allocate().
     static constexpr size_t kAlignment = alignof(std::max_align_t);
+#endif
     // Minimum size this class will allocate at once.
     static constexpr size_t kMinAllocationSize = 1 << 10;
 
diff --git a/src/shaders/SkImageShader.cpp b/src/shaders/SkImageShader.cpp
index 2e3bba5332..b8fd426e13 100755
--- a/src/shaders/SkImageShader.cpp
+++ b/src/shaders/SkImageShader.cpp
@@ -89,7 +89,7 @@ static bool legacy_shader_can_handle(const SkMatrix& inv) {
     const SkRect src = inv.mapRect(SkRect::MakeWH(max_dev_coord, max_dev_coord));
 
     // take 1/4 of max signed 32bits so we have room to subtract local values
-    const SkScalar max_fixed32dot32 = SK_MaxS32 * 0.25f;
+    const SkScalar max_fixed32dot32 = float(SK_MaxS32) * 0.25f;
     if (!SkRect::MakeLTRB(-max_fixed32dot32, -max_fixed32dot32,
                           +max_fixed32dot32, +max_fixed32dot32).contains(src)) {
         return false;