diff --git a/src/commands/debug.rs b/src/commands/debug.rs
index c05bf97..0cb5437 100644
--- a/src/commands/debug.rs
+++ b/src/commands/debug.rs
@@ -1,4 +1,6 @@
 use anyhow::{bail, Context as _};
+use poise::AutocompleteChoice;
+use tracing::{debug, instrument};
 
 use super::super::{drql, Context};
 
@@ -34,11 +36,52 @@ async fn scan(
     Ok(())
 }
 
+#[instrument(skip_all, fields(query = query))]
+async fn parse_one_autocomplete(_ctx: Context<'_>, query: &str) -> Vec<AutocompleteChoice<String>> {
+    // When we encounter an error, we want to split it across multiple lines because Discord only
+    // gives us 100 characters for the 'name' field in AutocompleteChoice. We split as follows:
+    // 1. We always split on newlines within the error message.
+    // 2. For a single line of the error message, we split on whitespace.
+
+    // TODO: Move this to a function? It's sorta repetitive for both autocomplete functions
+    if let Err(e) = drql::parser::parse_drql(query) {
+        debug!("Returning parse error response to autocomplete: {e:#}");
+        format!("Encountered an error while parsing:\n{e:#}")
+            .split('\n')
+            .flat_map(|part| {
+                crate::util::wrap_string_vec(
+                    &part
+                        .split_whitespace()
+                        .map(std::string::ToString::to_string)
+                        .collect::<Vec<_>>(),
+                    " ",
+                    100,
+                )
+                .unwrap()
+            })
+            .map(|option| AutocompleteChoice {
+                name: option,
+                value: query.to_string(),
+            })
+            .collect::<Vec<_>>()
+    } else {
+        debug!("Returning \"Parsed successfully\" response to autocomplete");
+        vec![AutocompleteChoice {
+            name: "Parsed successfully. Send command to view AST.".to_string(),
+            value: query.to_string(),
+        }]
+    }
+}
+
 /// Parse a single DRQL query
+#[instrument(skip_all, fields(query = query))]
 #[poise::command(slash_command)]
 async fn parse_one(
     ctx: Context<'_>,
-    #[description = "The DRQL query to parse (DO NOT include @{})"] query: String,
+
+    #[description = "The DRQL query to parse (DO NOT include @{})"]
+    #[autocomplete = "parse_one_autocomplete"]
+    query: String,
 ) -> Result<(), anyhow::Error> {
     ctx.say(match drql::parser::parse_drql(query.as_str()) {
         Err(e) => format!("Encountered an error while parsing:\n\n```{e:?}```"),
@@ -49,11 +92,64 @@ async fn parse_one(
     Ok(())
 }
 
+#[instrument(skip_all, fields(query = query))]
+async fn reduce_autocomplete(_ctx: Context<'_>, query: &str) -> Vec<AutocompleteChoice<String>> {
+    match drql::scanner::scan(query)
+        .enumerate()
+        .map(|(n, chunk)| {
+            drql::parser::parse_drql(chunk).context(format!("Error parsing chunk {n}"))
+        })
+        .collect::<Result<Vec<_>, _>>()
+    {
+        // The same whitespace printing is done here. First split on newlines, then split on spaces.
+        Err(e) => {
+            debug!("Returning parse error response to autocomplete: {e:#}");
+            format!("Encountered an error while parsing:\n{e:#}")
+                .split('\n')
+                .flat_map(|part| {
+                    crate::util::wrap_string_vec(
+                        &part
+                            .split_whitespace()
+                            .map(std::string::ToString::to_string)
+                            .collect::<Vec<_>>(),
+                        " ",
+                        100,
+                    )
+                    .unwrap()
+                })
+                .map(|option| AutocompleteChoice {
+                    name: option,
+                    value: query.to_string(),
+                })
+                .collect::<Vec<_>>()
+        }
+
+        Ok(exprs) if exprs.is_empty() => {
+            debug!("Returning \"No chunks found\" response to autocomplete");
+            vec![AutocompleteChoice {
+                name: "No chunks found.".to_string(),
+                value: query.to_string(),
+            }]
+        }
+        Ok(_) => {
+            debug!("Returning \"Parsed successfully\" response to autocomplete");
+            vec![AutocompleteChoice {
+                name: "Parsed successfully. Send command to view reduced AST.".to_string(),
+                value: query.to_string(),
+            }]
+        }
+    }
+}
+
 /// Scan the input, parse each query, and finally reduce into one tree
+#[instrument(skip_all, fields(msg = msg))]
 #[poise::command(slash_command)]
 async fn reduce(
     ctx: Context<'_>,
-    #[description = "The message to scan"] msg: String,
+
+    #[description = "The message to scan"]
+    #[autocomplete = "reduce_autocomplete"]
+    msg: String,
 ) -> Result<(), anyhow::Error> {
     ctx.say(
         match drql::scanner::scan(msg.as_str())