diff --git a/provisionersdk/scripts/bootstrap_darwin.sh b/provisionersdk/scripts/bootstrap_darwin.sh
index 50c86324cbb86..df867f55877a7 100644
--- a/provisionersdk/scripts/bootstrap_darwin.sh
+++ b/provisionersdk/scripts/bootstrap_darwin.sh
@@ -1,11 +1,34 @@
 #!/usr/bin/env sh
 set -eux pipefail
-trap "echo === Agent script exited with non-zero code. Sleeping 24h to preserve logs... && sleep 86400" EXIT
+# Sleep for a good long while before exiting.
+# This is to allow folks to exec into a failed workspace and poke around to
+# troubleshoot.
+waitonexit() {
+	echo "=== Agent script exited with non-zero code. Sleeping 24h to preserve logs..."
+	sleep 86400
+}
+trap waitonexit EXIT
 BINARY_DIR=$(mktemp -d -t coder.XXXXXX)
 BINARY_NAME=coder
+BINARY_URL=${ACCESS_URL}bin/coder-darwin-${ARCH}
 cd "$BINARY_DIR"
-curl -fsSL --compressed "${ACCESS_URL}bin/coder-darwin-${ARCH}" -o "${BINARY_NAME}"
-chmod +x $BINARY_NAME
+# Attempt to download the coder agent.
+# This could fail for a number of reasons, many of which are likely transient.
+# So just keep trying!
+while :; do
+	curl -fsSL --compressed "${BINARY_URL}" -o "${BINARY_NAME}" && break
+	status=$?
+	echo "error: failed to download coder agent using curl"
+	echo "curl exit code: ${status}"
+	echo "Trying again in 30 seconds..."
+	sleep 30
+done
+
+if ! chmod +x $BINARY_NAME; then
+	echo "Failed to make $BINARY_NAME executable"
+	exit 1
+fi
+
 export CODER_AGENT_AUTH="${AUTH_TYPE}"
 export CODER_AGENT_URL="${ACCESS_URL}"
 exec ./$BINARY_NAME agent
diff --git a/provisionersdk/scripts/bootstrap_linux.sh b/provisionersdk/scripts/bootstrap_linux.sh
index 06e9fe4973928..336a69ed5b75b 100644
--- a/provisionersdk/scripts/bootstrap_linux.sh
+++ b/provisionersdk/scripts/bootstrap_linux.sh
@@ -1,21 +1,48 @@
 #!/usr/bin/env sh
 set -eux pipefail
-trap "echo === Agent script exited with non-zero code. Sleeping 24h to preserve logs... && sleep 86400" EXIT
+# Sleep for a good long while before exiting.
+# This is to allow folks to exec into a failed workspace and poke around to
+# troubleshoot.
+waitonexit() {
+	echo "=== Agent script exited with non-zero code. Sleeping 24h to preserve logs..."
+	sleep 86400
+}
+trap waitonexit EXIT
 BINARY_DIR=$(mktemp -d -t coder.XXXXXX)
 BINARY_NAME=coder
 BINARY_URL=${ACCESS_URL}bin/coder-linux-${ARCH}
 cd "$BINARY_DIR"
-if command -v curl >/dev/null 2>&1; then
-	curl -fsSL --compressed "${BINARY_URL}" -o "${BINARY_NAME}"
-elif command -v wget >/dev/null 2>&1; then
-	wget -q "${BINARY_URL}" -O "${BINARY_NAME}"
-elif command -v busybox >/dev/null 2>&1; then
-	busybox wget -q "${BINARY_URL}" -O "${BINARY_NAME}"
-else
-	echo "error: no download tool found, please install curl, wget or busybox wget"
+# Attempt to download the coder agent.
+# This could fail for a number of reasons, many of which are likely transient.
+# So just keep trying!
+while :; do
+	# Try a number of different download tools, as we don't know what we'll
+	# have available
+	status=""
+	if command -v curl >/dev/null 2>&1; then
+		curl -fsSL --compressed "${BINARY_URL}" -o "${BINARY_NAME}" && break
+		status=$?
+	elif command -v wget >/dev/null 2>&1; then
+		wget -q "${BINARY_URL}" -O "${BINARY_NAME}" && break
+		status=$?
+	elif command -v busybox >/dev/null 2>&1; then
+		busybox wget -q "${BINARY_URL}" -O "${BINARY_NAME}" && break
+		status=$?
+	else
+		echo "error: no download tool found, please install curl, wget or busybox wget"
+		exit 127
+	fi
+	echo "error: failed to download coder agent"
+	echo "       command returned: ${status}"
+	echo "Trying again in 30 seconds..."
+	sleep 30
+done
+
+if ! chmod +x $BINARY_NAME; then
+	echo "Failed to make $BINARY_NAME executable"
 	exit 1
 fi
-chmod +x $BINARY_NAME
+
 export CODER_AGENT_AUTH="${AUTH_TYPE}"
 export CODER_AGENT_URL="${ACCESS_URL}"
 exec ./$BINARY_NAME agent
diff --git a/provisionersdk/scripts/bootstrap_windows.ps1 b/provisionersdk/scripts/bootstrap_windows.ps1
index 810012155bbc4..882df4a8cebaf 100644
--- a/provisionersdk/scripts/bootstrap_windows.ps1
+++ b/provisionersdk/scripts/bootstrap_windows.ps1
@@ -1,8 +1,31 @@
-# On Windows, VS Code Remote requires a parent process of the
-# executing shell to be named "sshd", otherwise it fails. See:
-# https://github.com/microsoft/vscode-remote-release/issues/5699
-$ProgressPreference = "SilentlyContinue"
-Invoke-WebRequest -Uri ${ACCESS_URL}bin/coder-windows-${ARCH}.exe -OutFile $env:TEMP\sshd.exe
+# Sleep for a while in case the underlying provider deletes the resource on error.
+trap {
+	Write-Error '=== Agent script exited with non-zero code. Sleeping 24h to preserve logs...'
+	Start-Sleep -Seconds 86400
+}
+
+# Attempt to download the coder agent.
+# This could fail for a number of reasons, many of which are likely transient.
+# So just keep trying!
+while ($true) {
+	try {
+		$ProgressPreference = "SilentlyContinue"
+		# On Windows, VS Code Remote requires a parent process of the
+		# executing shell to be named "sshd", otherwise it fails. See:
+		# https://github.com/microsoft/vscode-remote-release/issues/5699
+		$BINARY_URL="${ACCESS_URL}/bin/coder-windows-${ARCH}.exe"
+		Write-Output "Fetching coder agent from ${BINARY_URL}"
+		Invoke-WebRequest -Uri "${BINARY_URL}" -OutFile $env:TEMP\sshd.exe
+		break
+	} catch {
+		Write-Output "error: unhandled exception fetching coder agent:"
+		Write-Output $_
+		Write-Output "trying again in 30 seconds..."
+		Start-Sleep -Seconds 30
+	}
+}
+
+# If the below fails, retrying probably won't help.
 Set-MpPreference -DisableRealtimeMonitoring $true -ExclusionPath $env:TEMP\sshd.exe
 $env:CODER_AGENT_AUTH = "${AUTH_TYPE}"
 $env:CODER_AGENT_URL = "${ACCESS_URL}"
diff --git a/scripts/coder-dev.sh b/scripts/coder-dev.sh
index 138db49734596..bf2c423cb90c1 100755
--- a/scripts/coder-dev.sh
+++ b/scripts/coder-dev.sh
@@ -5,7 +5,7 @@
 set -euo pipefail
 
 SCRIPT_DIR=$(dirname "${BASH_SOURCE[0]}")
-# shellcheck disable=SC1091
+# shellcheck disable=SC1091,SC1090
 source "${SCRIPT_DIR}/lib.sh"
 PROJECT_ROOT=$(cd "$SCRIPT_DIR" && git rev-parse --show-toplevel)
 
diff --git a/scripts/develop.sh b/scripts/develop.sh
index 24c8e9e427571..0c91e30cb65d3 100755
--- a/scripts/develop.sh
+++ b/scripts/develop.sh
@@ -5,7 +5,7 @@
 set -euo pipefail
 
 SCRIPT_DIR=$(dirname "${BASH_SOURCE[0]}")
-# shellcheck disable=SC1091
+# shellcheck disable=SC1091,SC1090
 source "${SCRIPT_DIR}/lib.sh"
 PROJECT_ROOT=$(cd "$SCRIPT_DIR" && git rev-parse --show-toplevel)
 CODER_DEV_BIN="${PROJECT_ROOT}/.coderv2/coder"