diff --git a/terraform/config.tf b/terraform/config.tf
index e4dc6b26..72657117 100644
--- a/terraform/config.tf
+++ b/terraform/config.tf
@@ -38,6 +38,10 @@ variable "test_pypi_warehouse_token" {
   type      = string
   sensitive = true
 }
+variable "datadog_token" {
+  type      = string
+  sensitive = true
+}
 
 terraform {
   cloud {
diff --git a/terraform/file-hosting/fastly-service.tf b/terraform/file-hosting/fastly-service.tf
index 79cc4ee1..531b5295 100644
--- a/terraform/file-hosting/fastly-service.tf
+++ b/terraform/file-hosting/fastly-service.tf
@@ -75,12 +75,32 @@ resource "fastly_service_vcl" "files" {
     error_threshold       = 5
   }
 
+  backend {
+    name = "B2"
+    auto_loadbalance = false
+    shield = "iad-va-us"
+
+    request_condition = "Package File"
+    healthcheck = "B2 Health"
+
+    address = "${var.files_bucket}.s3.us-east-005.backblazeb2.com"
+    port = 443
+    use_ssl = true
+    ssl_cert_hostname = "${var.files_bucket}.s3.us-east-005.backblazeb2.com"
+    ssl_sni_hostname = "${var.files_bucket}.s3.us-east-005.backblazeb2.com"
+
+    connect_timeout       = 5000
+    first_byte_timeout    = 60000
+    between_bytes_timeout = 15000
+    error_threshold       = 5
+  }
+
   backend {
     name             = "GCS"
     auto_loadbalance = false
     shield           = "bfi-wa-us"
 
-    request_condition = "Package File"
+    request_condition = "NeverReq"
     healthcheck       = "GCS Health"
 
     address           = "${var.files_bucket}.storage.googleapis.com"
@@ -96,11 +116,31 @@ resource "fastly_service_vcl" "files" {
   }
 
   backend {
-    name              = "S3"
+    name              = "S3_Archive"
     auto_loadbalance  = false
+    shield            = "bfi-wa-us"
+
     request_condition = "NeverReq"
+    healthcheck       = "S3 Health"
+
+    address           = "${var.files_bucket}-archive.s3.amazonaws.com"
+    port              = 443
+    use_ssl           = true
+    ssl_cert_hostname = "${var.files_bucket}-archive.s3.amazonaws.com"
+    ssl_sni_hostname  = "${var.files_bucket}-archive.s3.amazonaws.com"
+
+    connect_timeout       = 5000
+    first_byte_timeout    = 60000
+    between_bytes_timeout = 15000
+    error_threshold       = 5
+  }
+
+  backend {
+    name              = "S3"
+    auto_loadbalance  = false
     shield            = "bfi-wa-us"
 
+    request_condition = "NeverReq"
     healthcheck = "S3 Health"
 
     address           = "${var.files_bucket}.s3.amazonaws.com"
@@ -201,6 +241,12 @@ resource "fastly_service_vcl" "files" {
     response_condition = "Never"
   }
 
+  logging_datadog {
+    name               = "DataDog Log"
+    token              = var.datadog_token
+    response_condition = "Package Served From Fallback"
+  }
+
   logging_s3 {
     name = "S3 Error Logs"
 
@@ -250,6 +296,12 @@ resource "fastly_service_vcl" "files" {
     type      = "RESPONSE"
     statement = "req.http.Fastly-Client-IP == \"127.0.0.1\" && req.http.Fastly-Client-IP != \"127.0.0.1\""
   }
+
+  condition {
+    name      = "Package Served From Fallback"
+    type      = "RESPONSE"
+    statement = "req.restarts == 0 && req.backend == S3 && req.url ~ \"^/packages/[a-f0-9]{2}/[a-f0-9]{2}/[a-f0-9]{60}/\" && http_status_matches(beresp.status, \"200\")"
+  }
 }
 
 resource "aws_route53_record" "files" {
diff --git a/terraform/file-hosting/main.tf b/terraform/file-hosting/main.tf
index 32c62389..15240db8 100644
--- a/terraform/file-hosting/main.tf
+++ b/terraform/file-hosting/main.tf
@@ -11,6 +11,7 @@ variable "aws_access_key_id" { type = string }
 variable "aws_secret_access_key" { type = string }
 variable "gcs_access_key_id" { type = string }
 variable "gcs_secret_access_key" { type = string }
+variable "datadog_token" { type = string }
 
 variable "fastly_endpoints" { type = map(any) }
 variable "domain_map" { type = map(any) }
diff --git a/terraform/file-hosting/vcl/files.vcl b/terraform/file-hosting/vcl/files.vcl
index bc6c371d..74160ec2 100644
--- a/terraform/file-hosting/vcl/files.vcl
+++ b/terraform/file-hosting/vcl/files.vcl
@@ -75,13 +75,28 @@ sub vcl_recv {
     # Change our backend to S3 to look for the file there, re-enable clustering and continue
     # https://www.slideshare.net/Fastly/advanced-vcl-how-to-use-restart
     if (req.restarts > 0 && req.url ~ "^/packages/[a-f0-9]{2}/[a-f0-9]{2}/[a-f0-9]{60}/") {
-      set req.backend = F_S3;
+      set req.backend = F_GCS;
       set req.http.Fastly-Force-Shield = "1";
     }
 
-    # Requests that are for an *actual* file get disaptched to Amazon S3 instead of
-    # to our typical backends. We need to setup the request to correctly access
-    # S3 and to authorize ourselves to S3.
+    # Requests that are for an *actual* file get disaptched to object storage instead of
+    # to our typical backends.
+
+    # If our file request is being dispatched to B2, we need to setup the request to correctly
+    # access B2 and to authorize ourselves to B2 with S3 compatible auth.
+    if (req.backend == F_B2 && req.url ~ "^/packages/[a-f0-9]{2}/[a-f0-9]{2}/[a-f0-9]{60}/") {
+        # Setup our environment to better match what S3 expects/needs
+        set req.http.Host = var.B2-Bucket-Name "s3.us-east-005.backblazeb2.com";
+        set req.http.Date = now;
+        set req.url = regsuball(req.url, "\+", urlencode("+"));
+
+        # Compute the Authorization header that B2 requires to be able to
+        # access the files stored there.
+        set req.http.Authorization = "AWS " var.B2-Application-Key-ID":" digest.hmac_sha1_base64(var.B2-Application-Key, "GET" LF LF LF req.http.Date LF "/" var.S3-Bucket-Name req.url.path);
+    }
+
+    # If our file request is being dispatched to S3, we need to setup the request to correctly
+    # access S3 and to authorize ourselves to S3.
     if (req.backend == F_S3 && req.url ~ "^/packages/[a-f0-9]{2}/[a-f0-9]{2}/[a-f0-9]{60}/") {
         # Setup our environment to better match what S3 expects/needs
         set req.http.Host = var.S3-Bucket-Name ".s3.amazonaws.com";
@@ -92,6 +107,7 @@ sub vcl_recv {
         # access the files stored there.
         set req.http.Authorization = "AWS " var.AWS-Access-Key-ID ":" digest.hmac_sha1_base64(var.AWS-Secret-Access-Key, "GET" LF LF LF req.http.Date LF "/" var.S3-Bucket-Name req.url.path);
     }
+
     # If our file request is being dispatched to GCS, setup the request to correctly
     # access GCS and authorize ourselves with GCS interoperability credentials.
     if (req.backend == GCS && req.url ~ "^/packages/[a-f0-9]{2}/[a-f0-9]{2}/[a-f0-9]{60}/") {
@@ -126,9 +142,9 @@ sub vcl_fetch {
         set beresp.cacheable = true;
     }
 
-    # If we successfully got a 404 response from GCS for a Package URL restart
-    # to check S3 for the file!
-    if (req.restarts == 0 && req.backend == GCS && req.url ~ "^/packages/[a-f0-9]{2}/[a-f0-9]{2}/[a-f0-9]{60}/" && http_status_matches(beresp.status, "404")) {
+    # If we successfully got a 404 response from B2 for a Package URL restart
+    # to check GCS for the file!
+    if (req.restarts == 0 && req.backend == B2 && req.url ~ "^/packages/[a-f0-9]{2}/[a-f0-9]{2}/[a-f0-9]{60}/" && http_status_matches(beresp.status, "404")) {
       restart;
     }
 
diff --git a/terraform/main.tf b/terraform/main.tf
index 1dca4892..afdacf19 100644
--- a/terraform/main.tf
+++ b/terraform/main.tf
@@ -149,6 +149,7 @@ module "file-hosting" {
   files_bucket        = "pypi-files"
   mirror              = "mirror.dub1.pypi.io"
   s3_logging_keys     = var.fastly_s3_logging
+  datadog_token       = var.datadog_token
 
   aws_access_key_id     = var.aws_access_key_id
   aws_secret_access_key = var.aws_secret_access_key
@@ -177,6 +178,7 @@ module "test-file-hosting" {
   files_bucket        = "pypi-files-staging"
   mirror              = "test-mirror.dub1.pypi.io"
   s3_logging_keys     = var.fastly_s3_logging
+  datadog_token       = var.datadog_token
 
   aws_access_key_id     = var.aws_access_key_id
   aws_secret_access_key = var.aws_secret_access_key