diff --git a/src/github.rs b/src/github.rs
index 14d7a906..0dc04fd8 100644
--- a/src/github.rs
+++ b/src/github.rs
@@ -16,6 +16,8 @@ use std::{
 };
 use tracing as log;
 
+pub mod labels;
+
 pub type UserId = u64;
 pub type PullRequestNumber = u64;
 
@@ -565,38 +567,15 @@ impl IssueRepository {
         format!("{}/{}", self.organization, self.repository)
     }
 
-    async fn has_label(&self, client: &GithubClient, label: &str) -> anyhow::Result<bool> {
-        #[allow(clippy::redundant_pattern_matching)]
-        let url = format!("{}/labels/{}", self.url(client), label);
-        match client.send_req(client.get(&url)).await {
-            Ok(_) => Ok(true),
-            Err(e) => {
-                if e.downcast_ref::<reqwest::Error>()
-                    .map_or(false, |e| e.status() == Some(StatusCode::NOT_FOUND))
-                {
-                    Ok(false)
-                } else {
-                    Err(e)
-                }
-            }
-        }
-    }
-}
-
-#[derive(Debug)]
-pub(crate) struct UnknownLabels {
-    labels: Vec<String>,
-}
-
-// NOTE: This is used to post the Github comment; make sure it's valid markdown.
-impl fmt::Display for UnknownLabels {
-    fn fmt(&self, f: &mut fmt::Formatter) -> fmt::Result {
-        write!(f, "Unknown labels: {}", &self.labels.join(", "))
+    async fn labels(&self, client: &GithubClient) -> anyhow::Result<Vec<Label>> {
+        let url = format!("{}/labels", self.url(client));
+        client
+            .json(client.get(&url))
+            .await
+            .context("failed to get labels")
     }
 }
 
-impl std::error::Error for UnknownLabels {}
-
 impl Issue {
     pub fn to_zulip_github_reference(&self) -> ZulipGitHubReference {
         ZulipGitHubReference {
@@ -730,8 +709,39 @@ impl Issue {
         Ok(())
     }
 
+    async fn normalize_and_match_labels(
+        &self,
+        client: &GithubClient,
+        requested_labels: &[&str],
+    ) -> anyhow::Result<Vec<String>> {
+        let available_labels = self
+            .repository()
+            .labels(client)
+            .await
+            .context("unable to retrieve the repository labels")?;
+
+        labels::normalize_and_match_labels(
+            &available_labels
+                .iter()
+                .map(|l| l.name.as_str())
+                .collect::<Vec<_>>(),
+            requested_labels,
+        )
+    }
+
     pub async fn remove_label(&self, client: &GithubClient, label: &str) -> anyhow::Result<()> {
         log::info!("remove_label from {}: {:?}", self.global_id(), label);
+
+        let normalized_labels = self.normalize_and_match_labels(client, &[label]).await?;
+        let label = normalized_labels
+            .first()
+            .context("failed to find label on repository")?;
+        log::info!(
+            "remove_label from {}: matched label to {:?}",
+            self.global_id(),
+            label
+        );
+
         // DELETE /repos/:owner/:repo/issues/:number/labels/{name}
         let url = format!(
             "{repo_url}/issues/{number}/labels/{name}",
@@ -767,6 +777,19 @@ impl Issue {
         labels: Vec<Label>,
     ) -> anyhow::Result<()> {
         log::info!("add_labels: {} +{:?}", self.global_id(), labels);
+
+        let labels = self
+            .normalize_and_match_labels(
+                client,
+                &labels.iter().map(|l| l.name.as_str()).collect::<Vec<_>>(),
+            )
+            .await?;
+        log::info!(
+            "add_labels: {} matched requested labels to +{:?}",
+            self.global_id(),
+            labels
+        );
+
         // POST /repos/:owner/:repo/issues/:number/labels
         // repo_url = https://api.github.com/repos/Codertocat/Hello-World
         let url = format!(
@@ -778,8 +801,7 @@ impl Issue {
         // Don't try to add labels already present on this issue.
         let labels = labels
             .into_iter()
-            .filter(|l| !self.labels().contains(&l))
-            .map(|l| l.name)
+            .filter(|l| !self.labels().iter().any(|existing| existing.name == *l))
             .collect::<Vec<_>>();
 
         log::info!("add_labels: {} filtered to {:?}", self.global_id(), labels);
@@ -788,32 +810,13 @@ impl Issue {
             return Ok(());
         }
 
-        let mut unknown_labels = vec![];
-        let mut known_labels = vec![];
-        for label in labels {
-            if !self.repository().has_label(client, &label).await? {
-                unknown_labels.push(label);
-            } else {
-                known_labels.push(label);
-            }
-        }
-
-        if !unknown_labels.is_empty() {
-            return Err(UnknownLabels {
-                labels: unknown_labels,
-            }
-            .into());
-        }
-
         #[derive(serde::Serialize)]
         struct LabelsReq {
             labels: Vec<String>,
         }
 
         client
-            .send_req(client.post(&url).json(&LabelsReq {
-                labels: known_labels,
-            }))
+            .send_req(client.post(&url).json(&LabelsReq { labels }))
             .await
             .context("failed to add labels")?;
 
@@ -3217,16 +3220,3 @@ impl Submodule {
         client.repository(fullname).await
     }
 }
-
-#[cfg(test)]
-mod tests {
-    use super::*;
-
-    #[test]
-    fn display_labels() {
-        let x = UnknownLabels {
-            labels: vec!["A-bootstrap".into(), "xxx".into()],
-        };
-        assert_eq!(x.to_string(), "Unknown labels: A-bootstrap, xxx");
-    }
-}
diff --git a/src/github/labels.rs b/src/github/labels.rs
new file mode 100644
index 00000000..c894c40a
--- /dev/null
+++ b/src/github/labels.rs
@@ -0,0 +1,162 @@
+use std::{fmt, sync::LazyLock};
+
+use itertools::Itertools;
+use regex::Regex;
+
+static EMOJI_REGEX: LazyLock<Regex> =
+    LazyLock::new(|| Regex::new(r"[\p{Emoji}\p{Emoji_Presentation}]").unwrap());
+
+pub(crate) fn normalize_and_match_labels(
+    available_labels: &[&str],
+    requested_labels: &[&str],
+) -> anyhow::Result<Vec<String>> {
+    let normalize = |s: &str| EMOJI_REGEX.replace_all(s, "").trim().to_lowercase();
+
+    let mut found_labels = Vec::<String>::with_capacity(requested_labels.len());
+    let mut unknown_labels = Vec::new();
+
+    for requested_label in requested_labels {
+        // First look for an exact match
+        if let Some(found) = available_labels.iter().find(|l| **l == *requested_label) {
+            found_labels.push((*found).into());
+            continue;
+        }
+
+        // Try normalizing requested label (remove emoji, case insensitive, trim whitespace)
+        let normalized_requested: String = normalize(requested_label);
+
+        // Find matching labels by normalized name
+        let found = available_labels
+            .iter()
+            .filter(|l| normalize(l) == normalized_requested)
+            .collect::<Vec<_>>();
+
+        match found[..] {
+            [] => {
+                unknown_labels.push(requested_label);
+            }
+            [label] => {
+                found_labels.push((*label).into());
+            }
+            [..] => {
+                return Err(AmbiguousLabelMatch {
+                    requested_label: requested_label.to_string(),
+                    labels: found.into_iter().map(|l| (*l).into()).collect(),
+                }
+                .into());
+            }
+        };
+    }
+
+    if !unknown_labels.is_empty() {
+        return Err(UnknownLabels {
+            labels: unknown_labels.iter().map(|s| s.to_string()).collect(),
+        }
+        .into());
+    }
+
+    Ok(found_labels)
+}
+
+#[derive(Debug)]
+pub(crate) struct UnknownLabels {
+    labels: Vec<String>,
+}
+
+// NOTE: This is used to post the Github comment; make sure it's valid markdown.
+impl fmt::Display for UnknownLabels {
+    fn fmt(&self, f: &mut fmt::Formatter) -> fmt::Result {
+        write!(f, "Unknown labels: {}", &self.labels.join(", "))
+    }
+}
+
+impl std::error::Error for UnknownLabels {}
+
+#[derive(Debug)]
+pub(crate) struct AmbiguousLabelMatch {
+    pub requested_label: String,
+    pub labels: Vec<String>,
+}
+
+// NOTE: This is used to post the Github comment; make sure it's valid markdown.
+impl fmt::Display for AmbiguousLabelMatch {
+    fn fmt(&self, f: &mut fmt::Formatter) -> fmt::Result {
+        write!(
+            f,
+            "Unsure which label to use for `{}` - could be one of: {}",
+            self.requested_label,
+            self.labels.iter().map(|l| format!("`{}`", l)).join(", ")
+        )
+    }
+}
+
+impl std::error::Error for AmbiguousLabelMatch {}
+
+#[cfg(test)]
+mod tests {
+    use super::*;
+
+    #[test]
+    fn display_unknown_labels_error() {
+        let x = UnknownLabels {
+            labels: vec!["A-bootstrap".into(), "xxx".into()],
+        };
+        assert_eq!(x.to_string(), "Unknown labels: A-bootstrap, xxx");
+    }
+
+    #[test]
+    fn display_ambiguous_label_error() {
+        let x = AmbiguousLabelMatch {
+            requested_label: "A-bootstrap".into(),
+            labels: vec!["A-bootstrap".into(), "A-bootstrap-2".into()],
+        };
+        assert_eq!(
+            x.to_string(),
+            "Unsure which label to use for `A-bootstrap` - could be one of: `A-bootstrap`, `A-bootstrap-2`"
+        );
+    }
+
+    #[test]
+    fn normalize_and_match_labels_happy_path() {
+        let available_labels = vec!["A-bootstrap 😺", "B-foo 👾", "C-bar", "C-bar 😦"];
+        let requested_labels = vec!["A-bootstrap", "B-foo", "C-bar"];
+
+        let result = normalize_and_match_labels(&available_labels, &requested_labels);
+
+        assert!(result.is_ok());
+        let found_labels = result.unwrap();
+        assert_eq!(found_labels.len(), 3);
+        assert_eq!(found_labels[0], "A-bootstrap 😺");
+        assert_eq!(found_labels[1], "B-foo 👾");
+        assert_eq!(found_labels[2], "C-bar");
+    }
+
+    #[test]
+    fn normalize_and_match_labels_no_match() {
+        let available_labels = vec!["A-bootstrap", "B-foo"];
+        let requested_labels = vec!["A-bootstrap", "C-bar"];
+
+        let result = normalize_and_match_labels(&available_labels, &requested_labels);
+
+        assert!(result.is_err());
+        let err = result.unwrap_err();
+        assert!(err.is::<UnknownLabels>());
+        let unknown = err.downcast::<UnknownLabels>().unwrap();
+        assert_eq!(unknown.labels, vec!["C-bar"]);
+    }
+
+    #[test]
+    fn normalize_and_match_labels_ambiguous_match() {
+        let available_labels = vec!["A-bootstrap 😺", "A-bootstrap 👾"];
+        let requested_labels = vec!["A-bootstrap"];
+
+        let result = normalize_and_match_labels(&available_labels, &requested_labels);
+
+        assert!(result.is_err());
+        let err = result.unwrap_err();
+        assert!(err.is::<AmbiguousLabelMatch>());
+        let ambiguous = err.downcast::<AmbiguousLabelMatch>().unwrap();
+        assert_eq!(ambiguous.requested_label, "A-bootstrap");
+        assert_eq!(ambiguous.labels, vec!["A-bootstrap 😺", "A-bootstrap 👾"]);
+    }
+}
diff --git a/src/handlers/assign.rs b/src/handlers/assign.rs
index 42e9f3e9..7912e4f9 100644
--- a/src/handlers/assign.rs
+++ b/src/handlers/assign.rs
@@ -22,7 +22,7 @@
 
 use crate::db::issue_data::IssueData;
 use crate::db::review_prefs::{RotationMode, get_review_prefs_batch};
-use crate::github::UserId;
+use crate::github::{UserId, labels};
 use crate::handlers::pr_tracking::ReviewerWorkqueue;
 use crate::{
     config::AssignConfig,
@@ -563,7 +563,7 @@ pub(super) async fn handle_command(
                         .add_labels(&ctx.github, vec![github::Label { name: t_label }])
                         .await
                     {
-                        if let Some(github::UnknownLabels { .. }) = err.downcast_ref() {
+                        if let Some(labels::UnknownLabels { .. }) = err.downcast_ref() {
                             log::warn!("Error assigning label: {}", err);
                         } else {
                             return Err(err);
diff --git a/src/handlers/autolabel.rs b/src/handlers/autolabel.rs
index 52eb8df4..d6a78d37 100644
--- a/src/handlers/autolabel.rs
+++ b/src/handlers/autolabel.rs
@@ -1,6 +1,6 @@
 use crate::{
     config::AutolabelConfig,
-    github::{IssuesAction, IssuesEvent, Label},
+    github::{IssuesAction, IssuesEvent, Label, labels::UnknownLabels},
     handlers::Context,
 };
 use anyhow::Context as _;
@@ -209,7 +209,6 @@ pub(super) async fn handle_input(
     match event.issue.add_labels(&ctx.github, input.add).await {
         Ok(()) => {}
         Err(e) => {
-            use crate::github::UnknownLabels;
             if let Some(err @ UnknownLabels { .. }) = e.downcast_ref() {
                 event
                     .issue
diff --git a/src/handlers/relabel.rs b/src/handlers/relabel.rs
index 31c5908e..93e9b6d4 100644
--- a/src/handlers/relabel.rs
+++ b/src/handlers/relabel.rs
@@ -11,8 +11,7 @@
 use crate::team_data::TeamClient;
 use crate::{
     config::RelabelConfig,
-    github::UnknownLabels,
-    github::{self, Event},
+    github::{self, Event, labels::UnknownLabels},
     handlers::Context,
     interactions::ErrorComment,
 };