diff --git a/Cargo.lock b/Cargo.lock
index f5cba5341..88b38d469 100644
--- a/Cargo.lock
+++ b/Cargo.lock
@@ -2396,6 +2396,7 @@ dependencies = [
  "flate2 1.0.11 (registry+https://github.com/rust-lang/crates.io-index)",
  "fs2 0.4.3 (registry+https://github.com/rust-lang/crates.io-index)",
  "fs_extra 1.1.0 (registry+https://github.com/rust-lang/crates.io-index)",
+ "http 0.1.18 (registry+https://github.com/rust-lang/crates.io-index)",
  "lazy_static 1.3.0 (registry+https://github.com/rust-lang/crates.io-index)",
  "log 0.4.8 (registry+https://github.com/rust-lang/crates.io-index)",
  "notify 4.0.12 (registry+https://github.com/rust-lang/crates.io-index)",
diff --git a/Cargo.toml b/Cargo.toml
index 9176404e2..613fc8549 100644
--- a/Cargo.toml
+++ b/Cargo.toml
@@ -42,6 +42,7 @@ ws = "0.9.0"
 url = "2.1.0"
 walkdir = "2.2.9"
 percent-encoding = "1.0.1"
+http = "0.1.1"
 
 [dev-dependencies]
 assert_cmd = "0.11.1"
diff --git a/src/commands/kv/delete_bulk.rs b/src/commands/kv/delete_bulk.rs
index 3fbf6a112..6c37398e2 100644
--- a/src/commands/kv/delete_bulk.rs
+++ b/src/commands/kv/delete_bulk.rs
@@ -12,6 +12,8 @@ use failure::bail;
 
 use crate::terminal::message;
 
+const MAX_PAIRS: usize = 10000;
+
 pub fn delete_bulk(namespace_id: &str, filename: &Path) -> Result<(), failure::Error> {
     let client = super::api_client()?;
     let account_id = super::account_id()?;
@@ -36,10 +38,21 @@ pub fn delete_bulk(namespace_id: &str, filename: &Path) -> Result<(), failure::E
         Err(e) => bail!(e),
     };
 
+    // Validate that bulk delete is within API constraints
+    let keys = keys?;
+    // Check number of pairs is under limit
+    if keys.len() > MAX_PAIRS {
+        bail!(
+            "Number of keys to delete ({}) exceeds max of {}",
+            keys.len(),
+            MAX_PAIRS
+        );
+    }
+
     let response = client.request(&DeleteBulk {
         account_identifier: &account_id,
         namespace_identifier: namespace_id,
-        bulk_keys: keys?,
+        bulk_keys: keys,
     });
 
     match response {
diff --git a/src/commands/kv/mod.rs b/src/commands/kv/mod.rs
index e9b0819bb..e15bbbad3 100644
--- a/src/commands/kv/mod.rs
+++ b/src/commands/kv/mod.rs
@@ -4,6 +4,7 @@ use std::path::Path;
 use cloudflare::framework::auth::Credentials;
 use cloudflare::framework::response::ApiFailure;
 use cloudflare::framework::HttpApiClient;
+use http::status::StatusCode;
 use failure::bail;
 
 use crate::settings;
@@ -48,7 +49,8 @@ fn account_id() -> Result<String, failure::Error> {
 
 fn print_error(e: ApiFailure) {
     match e {
-        ApiFailure::Error(_status, api_errors) => {
+        ApiFailure::Error(status, api_errors) => {
+            give_status_code_context(status);
             for error in api_errors.errors {
                 message::warn(&format!("Error {}: {}", error.code, error.message));
 
@@ -62,6 +64,15 @@ fn print_error(e: ApiFailure) {
     }
 }
 
+// For handling cases where the API gateway returns errors via HTTP status codes
+// (no KV error code is given).
+fn give_status_code_context(status_code: StatusCode) {
+    match status_code {
+        StatusCode::PAYLOAD_TOO_LARGE => message::warn("Returned status code 413, Payload Too Large. Make sure your upload is less than 100MB in size"),
+        _ => (),
+    }
+}
+
 fn help(error_code: u16) -> &'static str {
     // https://api.cloudflare.com/#workers-kv-namespace-errors
     match error_code {
diff --git a/src/commands/kv/write_bulk.rs b/src/commands/kv/write_bulk.rs
index 41f209b07..072b63f3a 100644
--- a/src/commands/kv/write_bulk.rs
+++ b/src/commands/kv/write_bulk.rs
@@ -13,6 +13,8 @@ use failure::bail;
 
 use crate::terminal::message;
 
+const MAX_PAIRS: usize = 10000;
+
 pub fn write_bulk(namespace_id: &str, filename: &Path) -> Result<(), failure::Error> {
     let client = super::api_client()?;
     let account_id = super::account_id()?;
@@ -38,10 +40,22 @@ pub fn write_bulk(namespace_id: &str, filename: &Path) -> Result<(), failure::Er
         Err(e) => bail!(e),
     };
 
+    // Validate that bulk upload is within size constraints
+    let pairs = pairs?;
+    if pairs.len() > MAX_PAIRS {
+        bail!(
+            "Number of key-value pairs to upload ({}) exceeds max of {}",
+            pairs.len(),
+            MAX_PAIRS
+        );
+    }
+
+    message::working("Parsing successful. Uploading all files above");
+
     let response = client.request(&WriteBulk {
         account_identifier: &account_id,
         namespace_identifier: namespace_id,
-        bulk_key_value_pairs: pairs?,
+        bulk_key_value_pairs: pairs,
     });
 
     match response {
@@ -64,7 +78,7 @@ fn parse_directory(directory: &Path) -> Result<Vec<KeyValuePair>, failure::Error
 
             // Need to base64 encode value
             let b64_value = base64::encode(&value);
-            message::working(&format!("Uploading {}...", key.clone()));
+            message::working(&format!("Parsing {}...", key.clone()));
             upload_vec.push(KeyValuePair {
                 key: key,
                 value: b64_value,