diff --git a/Cargo.lock b/Cargo.lock
index 140a33270..4d3e8eb37 100644
--- a/Cargo.lock
+++ b/Cargo.lock
@@ -2100,6 +2100,7 @@ dependencies = [
  "crossterm_winapi",
  "ctrlc",
  "hamcrest2",
+ "is_executable",
  "itertools",
  "log",
  "miette",
diff --git a/Cargo.toml b/Cargo.toml
index 57ba6898b..7085066cc 100644
--- a/Cargo.toml
+++ b/Cargo.toml
@@ -54,6 +54,8 @@ nu-term-grid = { path = "./crates/nu-term-grid", version = "0.59.0"  }
 pretty_env_logger = "0.4.0"
 rayon = "1.5.1"
 reedline = { git = "https://github.com/nushell/reedline", branch = "main" }
+is_executable = "1.0.1"
+
 # mimalloc = { version = "*", default-features = false }
 
 # Plugins
diff --git a/crates/nu-parser/src/lib.rs b/crates/nu-parser/src/lib.rs
index 13d1732c6..245a17abc 100644
--- a/crates/nu-parser/src/lib.rs
+++ b/crates/nu-parser/src/lib.rs
@@ -13,7 +13,9 @@ pub use known_external::KnownExternal;
 pub use lex::{lex, Token, TokenContents};
 pub use lite_parse::{lite_parse, LiteBlock};
 
-pub use parser::{parse, parse_block, parse_external_call, trim_quotes, Import};
+pub use parser::{
+    is_math_expression_like, parse, parse_block, parse_external_call, trim_quotes, Import,
+};
 
 #[cfg(feature = "plugin")]
 pub use parse_keywords::parse_register;
diff --git a/crates/nu-parser/src/parser.rs b/crates/nu-parser/src/parser.rs
index ade875518..f7a2f8ae0 100644
--- a/crates/nu-parser/src/parser.rs
+++ b/crates/nu-parser/src/parser.rs
@@ -41,7 +41,13 @@ fn is_identifier_byte(b: u8) -> bool {
     b != b'.' && b != b'[' && b != b'(' && b != b'{'
 }
 
-fn is_math_expression_byte(b: u8) -> bool {
+pub fn is_math_expression_like(bytes: &[u8]) -> bool {
+    if bytes.is_empty() {
+        return false;
+    }
+
+    let b = bytes[0];
+
     b == b'0'
         || b == b'1'
         || b == b'2'
@@ -826,7 +832,13 @@ pub fn parse_call(
         // Find the longest group of words that could form a command
         let bytes = working_set.get_span_contents(*word_span);
 
-        if is_math_expression_byte(bytes[0]) {
+        if is_math_expression_like(bytes)
+            && !working_set
+                .permanent_state
+                .external_exceptions
+                .iter()
+                .any(|x| x == bytes)
+        {
             break;
         }
 
@@ -3446,7 +3458,13 @@ pub fn parse_expression(
 
     let bytes = working_set.get_span_contents(spans[pos]);
 
-    let (output, err) = if is_math_expression_byte(bytes[0]) {
+    let (output, err) = if is_math_expression_like(bytes)
+        && !working_set
+            .permanent_state
+            .external_exceptions
+            .iter()
+            .any(|x| x == bytes)
+    {
         parse_math_expression(working_set, &spans[pos..], None)
     } else {
         // For now, check for special parses of certain keywords
diff --git a/crates/nu-protocol/src/engine/engine_state.rs b/crates/nu-protocol/src/engine/engine_state.rs
index 08b3be252..581764b63 100644
--- a/crates/nu-protocol/src/engine/engine_state.rs
+++ b/crates/nu-protocol/src/engine/engine_state.rs
@@ -169,6 +169,9 @@ pub struct EngineState {
     pub env_vars: im::HashMap<String, Value>,
     #[cfg(feature = "plugin")]
     pub plugin_signatures: Option<PathBuf>,
+
+    // A list of external commands that look like math expressions
+    pub external_exceptions: Vec<Vec<u8>>,
 }
 
 pub const NU_VARIABLE_ID: usize = 0;
@@ -199,6 +202,7 @@ impl EngineState {
             env_vars: im::HashMap::new(),
             #[cfg(feature = "plugin")]
             plugin_signatures: None,
+            external_exceptions: vec![],
         }
     }
 
@@ -633,6 +637,7 @@ impl Default for EngineState {
 pub struct StateWorkingSet<'a> {
     pub permanent_state: &'a EngineState,
     pub delta: StateDelta,
+    pub external_commands: Vec<Vec<u8>>,
 }
 
 /// A delta (or change set) between the current global state and a possible future global state. Deltas
@@ -707,6 +712,7 @@ impl<'a> StateWorkingSet<'a> {
         Self {
             delta: StateDelta::new(),
             permanent_state,
+            external_commands: vec![],
         }
     }
 
diff --git a/src/main.rs b/src/main.rs
index 259589594..5a1237e4b 100644
--- a/src/main.rs
+++ b/src/main.rs
@@ -57,6 +57,10 @@ fn main() -> Result<()> {
     };
     let _ = engine_state.merge_delta(delta, None, &init_cwd);
 
+    // Make a note of the exceptions we see for externals that look like math expressions
+    let exceptions = crate::utils::external_exceptions();
+    engine_state.external_exceptions = exceptions;
+
     // TODO: make this conditional in the future
     // Ctrl-c protection section
     let ctrlc = Arc::new(AtomicBool::new(false));
diff --git a/src/utils.rs b/src/utils.rs
index 95880dd73..0454d4a45 100644
--- a/src/utils.rs
+++ b/src/utils.rs
@@ -254,6 +254,32 @@ pub(crate) fn eval_source(
     true
 }
 
+/// Finds externals that have names that look like math expressions
+pub fn external_exceptions() -> Vec<Vec<u8>> {
+    let mut executables = vec![];
+
+    if let Ok(path) = std::env::var("PATH") {
+        for path in std::env::split_paths(&path) {
+            let path = path.to_string_lossy().to_string();
+
+            if let Ok(mut contents) = std::fs::read_dir(path) {
+                while let Some(Ok(item)) = contents.next() {
+                    if is_executable::is_executable(&item.path()) {
+                        if let Ok(name) = item.file_name().into_string() {
+                            let name = name.as_bytes().to_vec();
+                            if nu_parser::is_math_expression_like(&name) {
+                                executables.push(name);
+                            }
+                        }
+                    }
+                }
+            }
+        }
+    }
+
+    executables
+}
+
 #[cfg(windows)]
 pub fn enable_vt_processing() -> Result<(), ShellError> {
     use crossterm_winapi::{ConsoleMode, Handle};