diff --git a/utils/build/ssi/base/download_with_retry.sh b/utils/build/ssi/base/download_with_retry.sh
index c06e6249595..a9a9e7dc680 100644
--- a/utils/build/ssi/base/download_with_retry.sh
+++ b/utils/build/ssi/base/download_with_retry.sh
@@ -1,20 +1,44 @@
 #!/bin/bash
 
-download_with_retry() {
-    local url="$1"
-    local output
-    output="$(basename "$url")"
+run_with_retry() {
+    local description="$1"
+    local max_attempts="$2"
+    local retry_delay="$3"
+    shift 3
 
-    local max_attempts=5
     local attempt
     for (( attempt = 1; attempt <= max_attempts; attempt++ )); do
-        echo "[TRACE] downloading ${output} (attempt ${attempt}/${max_attempts})"
-        if curl --fail --retry 3 -sSL -o "$output" "$url" && [ -s "$output" ]; then
+        echo "[TRACE] running ${description} (attempt ${attempt}/${max_attempts})"
+        if "$@"; then
             return 0
         fi
-        rm -f "$output"
+
+        if (( attempt < max_attempts )); then
+            echo "[WARN] ${description} failed; retrying in ${retry_delay} seconds" >&2
+            sleep "$retry_delay"
+        fi
     done
 
-    echo "[ERROR] ${output} is missing or empty after ${max_attempts} attempts" >&2
+    echo "[ERROR] ${description} failed after ${max_attempts} attempts" >&2
     return 1
 }
+
+_download_once() {
+    local url="$1"
+    local output="$2"
+
+    if curl --fail --retry 3 -sSL -o "$output" "$url" && [ -s "$output" ]; then
+        return 0
+    fi
+
+    rm -f "$output"
+    return 1
+}
+
+download_with_retry() {
+    local url="$1"
+    local output
+    output="$(basename "$url")"
+
+    run_with_retry "download ${output}" 5 0 _download_once "$url" "$output"
+}
diff --git a/utils/build/ssi/base/install_script_ssi.sh b/utils/build/ssi/base/install_script_ssi.sh
index 1bac8e44551..71f239d0526 100755
--- a/utils/build/ssi/base/install_script_ssi.sh
+++ b/utils/build/ssi/base/install_script_ssi.sh
@@ -54,7 +54,18 @@ if [ ! -s "install_script_agent7.sh" ]; then
     exit 1
 fi
 
-DD_REPO_URL=${DD_injection_repo_url} DD_INSTALL_ONLY=true DD_APM_INSTRUMENTATION_ENABLED=host bash ./install_script_agent7.sh
+if ! run_with_retry \
+    "Datadog Agent installer" \
+    3 \
+    5 \
+    env \
+    "DD_REPO_URL=${DD_injection_repo_url}" \
+    DD_INSTALL_ONLY=true \
+    DD_APM_INSTRUMENTATION_ENABLED=host \
+    bash ./install_script_agent7.sh; then
+    echo "[ERROR] aborting SSI install after Datadog Agent installer failure" >&2
+    exit 1
+fi
 
 if [ -f /etc/debian_version ] || [ "$DISTRIBUTION" == "Debian" ] || [ "$DISTRIBUTION" == "Ubuntu" ]; then
     OS="Debian"
diff --git a/utils/build/ssi/base/install_script_ssi_installer.sh b/utils/build/ssi/base/install_script_ssi_installer.sh
index 336bda6ede2..9a2abe30633 100755
--- a/utils/build/ssi/base/install_script_ssi_installer.sh
+++ b/utils/build/ssi/base/install_script_ssi_installer.sh
@@ -5,4 +5,14 @@ source ./download_with_retry.sh
 
 download_with_retry https://dd-agent.s3.amazonaws.com/scripts/install_script_agent7.sh || exit 1
 
-DD_INSTALL_ONLY=true DD_INSTALLER=true bash ./install_script_agent7.sh
+if ! run_with_retry \
+    "Datadog Agent installer" \
+    3 \
+    5 \
+    env \
+    DD_INSTALL_ONLY=true \
+    DD_INSTALLER=true \
+    bash ./install_script_agent7.sh; then
+    echo "[ERROR] aborting SSI install after Datadog Agent installer failure" >&2
+    exit 1
+fi