diff --git a/.gitignore b/.gitignore
index 8632e8e308..415b319a38 100644
--- a/.gitignore
+++ b/.gitignore
@@ -28,14 +28,11 @@
 /external_binaries/
 /out/
 /vendor/.gclient
-/vendor/debian_jessie_amd64-sysroot/
-/vendor/debian_jessie_arm-sysroot/
-/vendor/debian_jessie_arm64-sysroot/
-/vendor/debian_jessie_i386-sysroot/
 /vendor/debian_jessie_mips64-sysroot/
-/vendor/debian_wheezy_amd64-sysroot/
-/vendor/debian_wheezy_arm-sysroot/
-/vendor/debian_wheezy_i386-sysroot/
+/vendor/debian_stretch_amd64-sysroot/
+/vendor/debian_stretch_arm-sysroot/
+/vendor/debian_stretch_arm64-sysroot/
+/vendor/debian_stretch_i386-sysroot/
 /vendor/gcc-4.8.3-d197-n64-loongson/
 /vendor/readme-gcc483-loongson.txt
 /vendor/download/
diff --git a/script/install-sysroot.py b/script/install-sysroot.py
index 05887a6f2d..463a81d9ea 100755
--- a/script/install-sysroot.py
+++ b/script/install-sysroot.py
@@ -85,11 +85,12 @@ def main(args):
 def InstallDefaultSysrootForArch(target_arch):
   if target_arch not in VALID_ARCHS:
     raise Error('Unknown architecture: %s' % target_arch)
-  InstallSysroot('Jessie', target_arch)
+  InstallSysroot('Stretch', target_arch)
 
 
 def InstallSysroot(target_platform, target_arch):
-  # The sysroot directory should match the one specified in build/common.gypi.
+  # The sysroot directory should match the one specified in
+  # build/config/sysroot.gni.
   # TODO(thestig) Consider putting this elsewhere to avoid having to recreate
   # it on every build.
   linux_dir = os.path.dirname(SCRIPT_DIR)
@@ -111,8 +112,6 @@ def InstallSysroot(target_platform, target_arch):
   if os.path.exists(stamp):
     with open(stamp) as s:
       if s.read() == url:
-        print '%s %s sysroot image already up to date: %s' % \
-            (target_platform, target_arch, sysroot)
         return
 
   print 'Installing Debian %s %s root image: %s' % \
diff --git a/script/sysroots.json b/script/sysroots.json
index 4aa73dad0e..7d60a06c42 100644
--- a/script/sysroots.json
+++ b/script/sysroots.json
@@ -1,56 +1,38 @@
 {
-    "jessie_amd64": {
-        "Revision": "d65c31e063bab0486665e087a1b4c5bb7bc7423c",
-        "Sha1Sum": "8b2167b36f3cd85ebbec5c2a39a1842ef613f6a2",
-        "SysrootDir": "debian_jessie_amd64-sysroot",
-        "Tarball": "debian_jessie_amd64_sysroot.tgz"
+    "stretch_amd64": {
+        "Revision": "961ad7bca2518fd9495e9d9676a8228ec8c54335",
+        "Sha1Sum": "c748f6e2de1f392bed9b69f8b5a0aaa12a2bea7d",
+        "SysrootDir": "debian_stretch_amd64-sysroot",
+        "Tarball": "debian_stretch_amd64_sysroot.tar.xz"
     },
-    "jessie_arm": {
-        "Revision": "d65c31e063bab0486665e087a1b4c5bb7bc7423c",
-        "Sha1Sum": "3fa13635be0c6d8ed461715ad51cdb3809a19422",
-        "SysrootDir": "debian_jessie_arm-sysroot",
-        "Tarball": "debian_jessie_arm_sysroot.tgz"
+    "stretch_arm": {
+        "Revision": "961ad7bca2518fd9495e9d9676a8228ec8c54335",
+        "Sha1Sum": "72cd0dae301971c69422f7290e608c1298571bd2",
+        "SysrootDir": "debian_stretch_arm-sysroot",
+        "Tarball": "debian_stretch_arm_sysroot.tar.xz"
     },
-    "jessie_arm64": {
-        "Revision": "d65c31e063bab0486665e087a1b4c5bb7bc7423c",
-        "Sha1Sum": "bcf92ed2a033b4b2d1032df3b53eac4910c78fde",
-        "SysrootDir": "debian_jessie_arm64-sysroot",
-        "Tarball": "debian_jessie_arm64_sysroot.tgz"
+    "stretch_arm64": {
+        "Revision": "961ad7bca2518fd9495e9d9676a8228ec8c54335",
+        "Sha1Sum": "06b19055e17c4f99c494e17f7422f0aaa2d62af6",
+        "SysrootDir": "debian_stretch_arm64-sysroot",
+        "Tarball": "debian_stretch_arm64_sysroot.tar.xz"
     },
-    "jessie_i386": {
-        "Revision": "d65c31e063bab0486665e087a1b4c5bb7bc7423c",
-        "Sha1Sum": "4e83ed9a1b457a1ca59512c3d4823e87e950deb4",
-        "SysrootDir": "debian_jessie_i386-sysroot",
-        "Tarball": "debian_jessie_i386_sysroot.tgz"
+    "stretch_i386": {
+        "Revision": "961ad7bca2518fd9495e9d9676a8228ec8c54335",
+        "Sha1Sum": "de4f82ec6400fd2e2e9a455f29155e7763de26c2",
+        "SysrootDir": "debian_stretch_i386-sysroot",
+        "Tarball": "debian_stretch_i386_sysroot.tar.xz"
     },
-    "jessie_mips": {
-        "Revision": "d65c31e063bab0486665e087a1b4c5bb7bc7423c",
-        "Sha1Sum": "0f550cd150f077a6e749a629e2fda0f0a4348eae",
-        "SysrootDir": "debian_jessie_mips-sysroot",
-        "Tarball": "debian_jessie_mips_sysroot.tgz"
+    "stretch_mips": {
+        "Revision": "961ad7bca2518fd9495e9d9676a8228ec8c54335",
+        "Sha1Sum": "256d581b85fb752f94da0b81004d2af878465cd6",
+        "SysrootDir": "debian_stretch_mips-sysroot",
+        "Tarball": "debian_stretch_mips_sysroot.tar.xz"
     },
-    "wheezy_amd64": {
-        "Revision": "d65c31e063bab0486665e087a1b4c5bb7bc7423c",
-        "Sha1Sum": "fe372c4394ece7fd1d853a205de8c13b46e2f45a",
-        "SysrootDir": "debian_wheezy_amd64-sysroot",
-        "Tarball": "debian_wheezy_amd64_sysroot.tgz"
-    },
-    "wheezy_arm": {
-        "Revision": "d65c31e063bab0486665e087a1b4c5bb7bc7423c",
-        "Sha1Sum": "73323fae0b5597398a38f0d7e64f48309da112fa",
-        "SysrootDir": "debian_wheezy_arm-sysroot",
-        "Tarball": "debian_wheezy_arm_sysroot.tgz"
-    },
-    "wheezy_i386": {
-        "Revision": "d65c31e063bab0486665e087a1b4c5bb7bc7423c",
-        "Sha1Sum": "7e96584297a5c9916b3bed4b88abe332fc79a247",
-        "SysrootDir": "debian_wheezy_i386-sysroot",
-        "Tarball": "debian_wheezy_i386_sysroot.tgz"
-    },
-    "wheezy_mips": {
-        "Revision": "d65c31e063bab0486665e087a1b4c5bb7bc7423c",
-        "Sha1Sum": "b2f173905a41ec9f23c329fe529508b4bdc76230",
-        "SysrootDir": "debian_wheezy_mips-sysroot",
-        "Tarball": "debian_wheezy_mips_sysroot.tgz"
+    "stretch_mips64el": {
+        "Revision": "961ad7bca2518fd9495e9d9676a8228ec8c54335",
+        "Sha1Sum": "6405f537c9ecee3a021749712fbca36ff7304bee",
+        "SysrootDir": "debian_stretch_mips64el-sysroot",
+        "Tarball": "debian_stretch_mips64el_sysroot.tar.xz"
     }
 }
diff --git a/toolchain.gypi b/toolchain.gypi
index 42552a4dae..aa9ce81ee7 100644
--- a/toolchain.gypi
+++ b/toolchain.gypi
@@ -53,16 +53,16 @@
             ['target_arch=="arm"', {
               # sysroot needs to be an absolute path otherwise it generates
               # incorrect results when passed to pkg-config
-              'sysroot%': '<(source_root)/vendor/debian_jessie_arm-sysroot',
+              'sysroot%': '<(source_root)/vendor/debian_stretch_arm-sysroot',
             }],
             ['target_arch=="arm64"', {
-              'sysroot%': '<(source_root)/vendor/debian_jessie_arm64-sysroot',
+              'sysroot%': '<(source_root)/vendor/debian_stretch_arm64-sysroot',
             }],
             ['target_arch=="ia32"', {
-              'sysroot%': '<(source_root)/vendor/debian_jessie_i386-sysroot',
+              'sysroot%': '<(source_root)/vendor/debian_stretch_i386-sysroot',
             }],
             ['target_arch=="x64"', {
-              'sysroot%': '<(source_root)/vendor/debian_jessie_amd64-sysroot',
+              'sysroot%': '<(source_root)/vendor/debian_stretch_amd64-sysroot',
             }],
             ['target_arch=="mips64el"', {
               'sysroot%': '<(source_root)/vendor/debian_jessie_mips64-sysroot',