diff --git a/synthtool/gcp/templates/python_library/.kokoro/docker/docs/Dockerfile b/synthtool/gcp/templates/python_library/.kokoro/docker/docs/Dockerfile
index 7323c42d0..f8137d0ae 100644
--- a/synthtool/gcp/templates/python_library/.kokoro/docker/docs/Dockerfile
+++ b/synthtool/gcp/templates/python_library/.kokoro/docker/docs/Dockerfile
@@ -68,7 +68,7 @@ RUN wget https://www.python.org/ftp/python/3.9.13/Python-3.9.13.tgz
 # Extract files
 RUN tar -xvf Python-3.9.13.tgz
 
-# Install python 3.9.11
+# Install python 3.9.13
 RUN ./Python-3.9.13/configure --enable-optimizations
 RUN make altinstall
 
diff --git a/synthtool/gcp/templates/python_library/.kokoro/requirements.in b/synthtool/gcp/templates/python_library/.kokoro/requirements.in
index 7718391a3..cbd7e77f4 100644
--- a/synthtool/gcp/templates/python_library/.kokoro/requirements.in
+++ b/synthtool/gcp/templates/python_library/.kokoro/requirements.in
@@ -5,4 +5,6 @@ typing-extensions
 twine
 wheel
 setuptools
-nox
\ No newline at end of file
+nox
+charset-normalizer<3
+click<8.1.0
diff --git a/synthtool/gcp/templates/python_library/.kokoro/requirements.txt b/synthtool/gcp/templates/python_library/.kokoro/requirements.txt
index 12bfbf433..9c1b9be34 100644
--- a/synthtool/gcp/templates/python_library/.kokoro/requirements.txt
+++ b/synthtool/gcp/templates/python_library/.kokoro/requirements.txt
@@ -93,11 +93,14 @@ cffi==1.15.1 \
 charset-normalizer==2.1.1 \
     --hash=sha256:5a3d016c7c547f69d6f81fb0db9449ce888b418b5b9952cc5e6e66843e9dd845 \
     --hash=sha256:83e9a75d1911279afd89352c68b45348559d1fc0506b054b346651b5e7fee29f
-    # via requests
-click==8.1.3 \
-    --hash=sha256:7682dc8afb30297001674575ea00d1814d808d6a36af415a82bd481d37ba7b8e \
-    --hash=sha256:bb4d8133cb15a609f44e8213d9b391b0809795062913b383c62be0ee95b1db48
     # via
+    #   -r requirements.in
+    #   requests
+click==8.0.4 \
+    --hash=sha256:6a7a62563bbfabfda3a38f3023a1db4a35978c0abd76f6c9605ecd6554d6d9b1 \
+    --hash=sha256:8458d7b1287c5fb128c90e23381cf99dcde74beaf6c7ff6384ce84d6fe090adb
+    # via
+    #   -r requirements.in
     #   gcp-docuploader
     #   gcp-releasetool
 colorlog==6.7.0 \
@@ -156,9 +159,9 @@ gcp-docuploader==0.6.4 \
     --hash=sha256:01486419e24633af78fd0167db74a2763974765ee8078ca6eb6964d0ebd388af \
     --hash=sha256:70861190c123d907b3b067da896265ead2eeb9263969d6955c9e0bb091b5ccbf
     # via -r requirements.in
-gcp-releasetool==1.9.1 \
-    --hash=sha256:952f4055d5d986b070ae2a71c4410b250000f9cc5a1e26398fcd55a5bbc5a15f \
-    --hash=sha256:d0d3c814a97c1a237517e837d8cfa668ced8df4b882452578ecef4a4e79c583b
+gcp-releasetool==1.10.0 \
+    --hash=sha256:72a38ca91b59c24f7e699e9227c90cbe4dd71b789383cb0164b088abae294c83 \
+    --hash=sha256:8c7c99320208383d4bb2b808c6880eb7a81424afe7cdba3c8d84b25f4f0e097d
     # via -r requirements.in
 google-api-core==2.10.2 \
     --hash=sha256:10c06f7739fe57781f87523375e8e1a3a4674bf6392cd6131a3222182b971320 \
@@ -166,9 +169,9 @@ google-api-core==2.10.2 \
     # via
     #   google-cloud-core
     #   google-cloud-storage
-google-auth==2.14.0 \
-    --hash=sha256:1ad5b0e6eba5f69645971abb3d2c197537d5914070a8c6d30299dfdb07c5c700 \
-    --hash=sha256:cf24817855d874ede2efd071aa22125445f555de1685b739a9782fcf408c2a3d
+google-auth==2.14.1 \
+    --hash=sha256:ccaa901f31ad5cbb562615eb8b664b3dd0bf5404a67618e642307f00613eda4d \
+    --hash=sha256:f5d8701633bebc12e0deea4df8abd8aff31c28b355360597f7f2ee60f2e4d016
     # via
     #   gcp-releasetool
     #   google-api-core
@@ -178,9 +181,9 @@ google-cloud-core==2.3.2 \
     --hash=sha256:8417acf6466be2fa85123441696c4badda48db314c607cf1e5d543fa8bdc22fe \
     --hash=sha256:b9529ee7047fd8d4bf4a2182de619154240df17fbe60ead399078c1ae152af9a
     # via google-cloud-storage
-google-cloud-storage==2.5.0 \
-    --hash=sha256:19a26c66c317ce542cea0830b7e787e8dac2588b6bfa4d3fd3b871ba16305ab0 \
-    --hash=sha256:382f34b91de2212e3c2e7b40ec079d27ee2e3dbbae99b75b1bcd8c63063ce235
+google-cloud-storage==2.6.0 \
+    --hash=sha256:104ca28ae61243b637f2f01455cc8a05e8f15a2a18ced96cb587241cdd3820f5 \
+    --hash=sha256:4ad0415ff61abdd8bb2ae81c1f8f7ec7d91a1011613f2db87c614c550f97bfe9
     # via gcp-docuploader
 google-crc32c==1.5.0 \
     --hash=sha256:024894d9d3cfbc5943f8f230e23950cd4906b2fe004c72e29b209420a1e6b05a \
@@ -256,9 +259,9 @@ google-resumable-media==2.4.0 \
     --hash=sha256:2aa004c16d295c8f6c33b2b4788ba59d366677c0a25ae7382436cb30f776deaa \
     --hash=sha256:8d5518502f92b9ecc84ac46779bd4f09694ecb3ba38a3e7ca737a86d15cbca1f
     # via google-cloud-storage
-googleapis-common-protos==1.56.4 \
-    --hash=sha256:8eb2cbc91b69feaf23e32452a7ae60e791e09967d81d4fcc7fc388182d1bd394 \
-    --hash=sha256:c25873c47279387cfdcbdafa36149887901d36202cb645a0e4f29686bf6e4417
+googleapis-common-protos==1.57.0 \
+    --hash=sha256:27a849d6205838fb6cc3c1c21cb9800707a661bb21c6ce7fb13e99eb1f8a0c46 \
+    --hash=sha256:a9f4a1d7f6d9809657b7f1316a1aa527f6664891531bcfcc13b6696e685f443c
     # via google-api-core
 idna==3.4 \
     --hash=sha256:814f528e8dead7d329833b91c5faa87d60bf71824cd12a7530b5526063d02cb4 \
@@ -269,6 +272,7 @@ importlib-metadata==5.0.0 \
     --hash=sha256:ddb0e35065e8938f867ed4928d0ae5bf2a53b7773871bfe6bcc7e4fcdc7dea43
     # via
     #   -r requirements.in
+    #   keyring
     #   twine
 jaraco-classes==3.2.3 \
     --hash=sha256:2353de3288bc6b82120752201c6b1c1a14b058267fa424ed5ce5984e3b922158 \
@@ -284,9 +288,9 @@ jinja2==3.1.2 \
     --hash=sha256:31351a702a408a9e7595a8fc6150fc3f43bb6bf7e319770cbc0db9df9437e852 \
     --hash=sha256:6088930bfe239f0e6710546ab9c19c9ef35e29792895fed6e6e31a023a182a61
     # via gcp-releasetool
-keyring==23.9.3 \
-    --hash=sha256:69732a15cb1433bdfbc3b980a8a36a04878a6cfd7cb99f497b573f31618001c0 \
-    --hash=sha256:69b01dd83c42f590250fe7a1f503fc229b14de83857314b1933a3ddbf595c4a5
+keyring==23.11.0 \
+    --hash=sha256:3dd30011d555f1345dec2c262f0153f2f0ca6bca041fb1dc4588349bb4c0ac1e \
+    --hash=sha256:ad192263e2cdd5f12875dedc2da13534359a7e760e77f8d04b50968a821c2361
     # via
     #   gcp-releasetool
     #   twine
@@ -350,9 +354,9 @@ pkginfo==1.8.3 \
     --hash=sha256:848865108ec99d4901b2f7e84058b6e7660aae8ae10164e015a6dcf5b242a594 \
     --hash=sha256:a84da4318dd86f870a9447a8c98340aa06216bfc6f2b7bdc4b8766984ae1867c
     # via twine
-platformdirs==2.5.2 \
-    --hash=sha256:027d8e83a2d7de06bbac4e5ef7e023c02b863d7ea5d079477e722bb41ab25788 \
-    --hash=sha256:58c8abb07dcb441e6ee4b11d8df0ac856038f944ab98b7be6b27b2a3c7feef19
+platformdirs==2.5.4 \
+    --hash=sha256:1006647646d80f16130f052404c6b901e80ee4ed6bef6792e1f238a8969106f7 \
+    --hash=sha256:af0276409f9a02373d540bf8480021a048711d572745aef4b7842dad245eba10
     # via virtualenv
 protobuf==3.20.3 \
     --hash=sha256:03038ac1cfbc41aa21f6afcbcd357281d7521b4157926f30ebecc8d4ea59dcb7 \
@@ -381,7 +385,6 @@ protobuf==3.20.3 \
     #   gcp-docuploader
     #   gcp-releasetool
     #   google-api-core
-    #   googleapis-common-protos
 py==1.11.0 \
     --hash=sha256:51c75c4126074b472f746a24399ad32f6053d1b34b68d2fa41e558e6f4a98719 \
     --hash=sha256:607c53218732647dff4acdfcd50cb62615cedf612e72d1724fb1a0cc6405b378
@@ -476,17 +479,17 @@ urllib3==1.26.12 \
     # via
     #   requests
     #   twine
-virtualenv==20.16.6 \
-    --hash=sha256:186ca84254abcbde98180fd17092f9628c5fe742273c02724972a1d8a2035108 \
-    --hash=sha256:530b850b523c6449406dfba859d6345e48ef19b8439606c5d74d7d3c9e14d76e
+virtualenv==20.16.7 \
+    --hash=sha256:8691e3ff9387f743e00f6bb20f70121f5e4f596cae754531f2b3b3a1b1ac696e \
+    --hash=sha256:efd66b00386fdb7dbe4822d172303f40cd05e50e01740b19ea42425cbe653e29
     # via nox
 webencodings==0.5.1 \
     --hash=sha256:a0af1213f3c2226497a97e2b3aa01a7e4bee4f403f95be16fc9acd2947514a78 \
     --hash=sha256:b36a1c245f2d304965eb4e0a82848379241dc04b865afcc4aab16748587e1923
     # via bleach
-wheel==0.37.1 \
-    --hash=sha256:4bdcd7d840138086126cd09254dc6195fb4fc6f01c050a1d7236f2630db1d22a \
-    --hash=sha256:e9a504e793efbca1b8e0e9cb979a249cf4a0a7b5b8c9e8b65a5e39d49529c1c4
+wheel==0.38.4 \
+    --hash=sha256:965f5259b566725405b05e7cf774052044b1ed30119b5d586b2703aafe8719ac \
+    --hash=sha256:b60533f3f5d530e971d6737ca6d58681ee434818fab630c83a734bb10c083ce8
     # via -r requirements.in
 zipp==3.10.0 \
     --hash=sha256:4fcb6f278987a6605757302a6e40e896257570d11c51628968ccb2a47e80c6c1 \
@@ -494,7 +497,7 @@ zipp==3.10.0 \
     # via importlib-metadata
 
 # The following packages are considered to be unsafe in a requirements file:
-setuptools==65.5.0 \
-    --hash=sha256:512e5536220e38146176efb833d4a62aa726b7bbff82cfbc8ba9eaa3996e0b17 \
-    --hash=sha256:f62ea9da9ed6289bfe868cd6845968a2c854d1427f8548d52cae02a42b4f0356
+setuptools==65.5.1 \
+    --hash=sha256:d0b9a8433464d5800cbe05094acf5c6d52a91bfac9b52bcfc4d41382be5d5d31 \
+    --hash=sha256:e197a19aa8ec9722928f2206f8de752def0e4c9fc6953527360d1c36d94ddb2f
     # via -r requirements.in