diff --git a/build/azure-pipelines/darwin/product-build-darwin-cli-sign.yml b/build/azure-pipelines/darwin/product-build-darwin-cli-sign.yml
index f8f581fcbfa..4557f65b99e 100644
--- a/build/azure-pipelines/darwin/product-build-darwin-cli-sign.yml
+++ b/build/azure-pipelines/darwin/product-build-darwin-cli-sign.yml
@@ -36,7 +36,7 @@ steps:
 
   - script: |
       set -e
-      for i in {1..3}; do # try 3 times
+      for i in {1..5}; do # try 5 times
         yarn --cwd build --frozen-lockfile --check-files && break
         if [ $i -eq 3 ]; then
           echo "Yarn failed too many times" >&2
diff --git a/build/azure-pipelines/darwin/product-build-darwin-sign.yml b/build/azure-pipelines/darwin/product-build-darwin-sign.yml
index c8596087023..a8133deecbd 100644
--- a/build/azure-pipelines/darwin/product-build-darwin-sign.yml
+++ b/build/azure-pipelines/darwin/product-build-darwin-sign.yml
@@ -90,7 +90,7 @@ steps:
       export npm_config_arch=$(VSCODE_ARCH)
       export npm_config_node_gyp=$(which node-gyp)
 
-      for i in {1..3}; do # try 3 times
+      for i in {1..5}; do # try 5 times
         yarn --frozen-lockfile --check-files && break
         if [ $i -eq 3 ]; then
           echo "Yarn failed too many times" >&2
diff --git a/build/azure-pipelines/darwin/product-build-darwin-universal.yml b/build/azure-pipelines/darwin/product-build-darwin-universal.yml
index b2995d408bc..44d09ed7fa9 100644
--- a/build/azure-pipelines/darwin/product-build-darwin-universal.yml
+++ b/build/azure-pipelines/darwin/product-build-darwin-universal.yml
@@ -90,7 +90,7 @@ steps:
       export npm_config_arch=$(VSCODE_ARCH)
       export npm_config_node_gyp=$(which node-gyp)
 
-      for i in {1..3}; do # try 3 times
+      for i in {1..5}; do # try 5 times
         yarn --frozen-lockfile --check-files && break
         if [ $i -eq 3 ]; then
           echo "Yarn failed too many times" >&2
diff --git a/build/azure-pipelines/darwin/product-build-darwin.yml b/build/azure-pipelines/darwin/product-build-darwin.yml
index cf005a97a2a..c554e9146b9 100644
--- a/build/azure-pipelines/darwin/product-build-darwin.yml
+++ b/build/azure-pipelines/darwin/product-build-darwin.yml
@@ -119,7 +119,7 @@ steps:
       export npm_config_arch=$(VSCODE_ARCH)
       export npm_config_node_gyp=$(which node-gyp)
 
-      for i in {1..3}; do # try 3 times
+      for i in {1..5}; do # try 5 times
         yarn --frozen-lockfile --check-files && break
         if [ $i -eq 3 ]; then
           echo "Yarn failed too many times" >&2
diff --git a/build/azure-pipelines/linux/product-build-alpine.yml b/build/azure-pipelines/linux/product-build-alpine.yml
index 87cff75e91b..5b8bad51650 100644
--- a/build/azure-pipelines/linux/product-build-alpine.yml
+++ b/build/azure-pipelines/linux/product-build-alpine.yml
@@ -103,7 +103,7 @@ steps:
 
   - script: |
       set -e
-      for i in {1..3}; do # try 3 times
+      for i in {1..5}; do # try 5 times
         yarn --frozen-lockfile --check-files --check-files && break
         if [ $i -eq 3 ]; then
           echo "Yarn failed too many times" >&2
diff --git a/build/azure-pipelines/linux/product-build-linux-client.yml b/build/azure-pipelines/linux/product-build-linux-client.yml
index bb9e7e1d62c..8f24ce4c0e5 100644
--- a/build/azure-pipelines/linux/product-build-linux-client.yml
+++ b/build/azure-pipelines/linux/product-build-linux-client.yml
@@ -145,7 +145,7 @@ steps:
   - script: |
       set -e
       node build/npm/setupBuildYarnrc
-      for i in {1..3}; do # try 3 times
+      for i in {1..5}; do # try 5 times
         yarn --cwd build --frozen-lockfile --check-files && break
         if [ $i -eq 3 ]; then
           echo "Yarn failed too many times" >&2
@@ -191,7 +191,7 @@ steps:
         export VSCODE_REMOTE_CXX=$(which g++)
       fi
 
-      for i in {1..3}; do # try 3 times
+      for i in {1..5}; do # try 5 times
         yarn --frozen-lockfile --check-files && break
         if [ $i -eq 3 ]; then
           echo "Yarn failed too many times" >&2
diff --git a/build/azure-pipelines/linux/scripts/install-remote-dependencies.sh b/build/azure-pipelines/linux/scripts/install-remote-dependencies.sh
index c6b4e3115f1..b5c316133d0 100755
--- a/build/azure-pipelines/linux/scripts/install-remote-dependencies.sh
+++ b/build/azure-pipelines/linux/scripts/install-remote-dependencies.sh
@@ -4,7 +4,7 @@ set -e
 echo "Installing remote dependencies"
 (cd remote && rm -rf node_modules)
 
-for i in {1..3}; do # try 3 times
+for i in {1..5}; do # try 5 times
   yarn --cwd remote --frozen-lockfile --check-files && break
   if [ $i -eq 3 ]; then
     echo "Yarn failed too many times" >&2
diff --git a/build/azure-pipelines/product-build-pr-cache.yml b/build/azure-pipelines/product-build-pr-cache.yml
index 73f17eea5ac..35c316555fd 100644
--- a/build/azure-pipelines/product-build-pr-cache.yml
+++ b/build/azure-pipelines/product-build-pr-cache.yml
@@ -52,7 +52,7 @@ steps:
 
   - script: |
       set -e
-      for i in {1..3}; do # try 3 times
+      for i in {1..5}; do # try 5 times
         yarn --frozen-lockfile --check-files && break
         if [ $i -eq 3 ]; then
           echo "Yarn failed too many times" >&2
diff --git a/build/azure-pipelines/product-compile.yml b/build/azure-pipelines/product-compile.yml
index 9da22cba292..e02eaad1bac 100644
--- a/build/azure-pipelines/product-compile.yml
+++ b/build/azure-pipelines/product-compile.yml
@@ -65,7 +65,7 @@ steps:
 
   - script: |
       set -e
-      for i in {1..3}; do # try 3 times
+      for i in {1..5}; do # try 5 times
         yarn --frozen-lockfile --check-files && break
         if [ $i -eq 3 ]; then
           echo "Yarn failed too many times" >&2
diff --git a/build/azure-pipelines/sdl-scan.yml b/build/azure-pipelines/sdl-scan.yml
index 98be5706e6d..0f151623bf1 100644
--- a/build/azure-pipelines/sdl-scan.yml
+++ b/build/azure-pipelines/sdl-scan.yml
@@ -221,7 +221,7 @@ stages:
 
           - script: |
               set -e
-              for i in {1..3}; do # try 3 times
+              for i in {1..5}; do # try 5 times
                 yarn --cwd build --frozen-lockfile --check-files && break
                 if [ $i -eq 3 ]; then
                   echo "Yarn failed too many times" >&2
@@ -254,7 +254,7 @@ stages:
                 export VSCODE_REMOTE_CXX=$(which g++)
               fi
 
-              for i in {1..3}; do # try 3 times
+              for i in {1..5}; do # try 5 times
                 yarn --frozen-lockfile --check-files && break
                 if [ $i -eq 3 ]; then
                   echo "Yarn failed too many times" >&2
diff --git a/build/azure-pipelines/web/product-build-web.yml b/build/azure-pipelines/web/product-build-web.yml
index bf308a3c8cb..ee6961ea733 100644
--- a/build/azure-pipelines/web/product-build-web.yml
+++ b/build/azure-pipelines/web/product-build-web.yml
@@ -91,7 +91,7 @@ steps:
 
   - script: |
       set -e
-      for i in {1..3}; do # try 3 times
+      for i in {1..5}; do # try 5 times
         yarn --frozen-lockfile --check-files && break
         if [ $i -eq 3 ]; then
           echo "Yarn failed too many times" >&2
diff --git a/build/azure-pipelines/win32/retry.ps1 b/build/azure-pipelines/win32/retry.ps1
index 002a5e274b7..0cc67f58c03 100644
--- a/build/azure-pipelines/win32/retry.ps1
+++ b/build/azure-pipelines/win32/retry.ps1
@@ -6,7 +6,7 @@ function Retry
 	)
 	$retry = 0
 
-	while ($retry++ -lt 3) {
+	while ($retry++ -lt 5) {
 		try {
 			& $cmd
 			return