diff --git a/src/aqua/aqua_registry.rs b/src/aqua/aqua_registry.rs
index ac4b3ceb18..c0c68d1c4d 100644
--- a/src/aqua/aqua_registry.rs
+++ b/src/aqua/aqua_registry.rs
@@ -2,13 +2,13 @@ use crate::backend::aqua;
 use crate::backend::aqua::{arch, os};
 use crate::duration::{DAILY, WEEKLY};
 use crate::git::{CloneOptions, Git};
+use crate::semver::split_version_prefix;
 use crate::{aqua::aqua_template, config::Settings};
 use crate::{dirs, file, hashmap, http};
 use expr::{Context, Program, Value};
 use eyre::{ContextCompat, Result, eyre};
 use indexmap::IndexSet;
 use itertools::Itertools;
-use regex::Regex;
 use serde_derive::Deserialize;
 use std::collections::HashMap;
 use std::path::PathBuf;
@@ -462,8 +462,8 @@ impl AquaPackage {
     }
 
     fn expr_parser(&self, v: &str) -> expr::Environment<'_> {
-        let prefix = Regex::new(r"^[^0-9.]+").unwrap();
-        let ver = versions::Versioning::new(prefix.replace(v, ""));
+        let (_, v) = split_version_prefix(v);
+        let ver = versions::Versioning::new(v);
         let mut env = expr::Environment::new();
         env.add_function("semver", move |c| {
             if c.args.len() != 1 {
diff --git a/src/main.rs b/src/main.rs
index 75272944ce..304839af59 100644
--- a/src/main.rs
+++ b/src/main.rs
@@ -69,6 +69,7 @@ mod redactions;
 mod registry;
 pub(crate) mod result;
 mod runtime_symlinks;
+mod semver;
 mod shell;
 mod shims;
 mod shorthands;
diff --git a/src/runtime_symlinks.rs b/src/runtime_symlinks.rs
index 6067c183b1..7c56433bf2 100644
--- a/src/runtime_symlinks.rs
+++ b/src/runtime_symlinks.rs
@@ -5,12 +5,12 @@ use crate::backend::Backend;
 use crate::config::{Alias, Config};
 use crate::file::make_symlink_or_file;
 use crate::plugins::VERSION_REGEX;
+use crate::semver::split_version_prefix;
 use crate::{backend, file};
 use eyre::Result;
 use indexmap::IndexMap;
 use itertools::Itertools;
 use versions::Versioning;
-use xx::regex;
 
 pub async fn rebuild(config: &Config) -> Result<()> {
     for backend in backend::list() {
@@ -39,14 +39,9 @@ fn list_symlinks(config: &Config, backend: Arc<dyn Backend>) -> IndexMap<String,
     // TODO: make this a pure function and add test cases
     let mut symlinks = IndexMap::new();
     let rel_path = |x: &String| PathBuf::from(".").join(x.clone());
-    let re = regex!(r"^[a-zA-Z0-9]+-");
     for v in installed_versions(&backend) {
-        let prefix = re
-            .find(&v)
-            .map(|s| s.as_str().to_string())
-            .unwrap_or_default();
-        let sans_prefix = v.trim_start_matches(&prefix);
-        let versions = Versioning::new(sans_prefix).unwrap_or_default();
+        let (prefix, version) = split_version_prefix(&v);
+        let versions = Versioning::new(version).unwrap_or_default();
         let mut partial = vec![];
         while versions.nth(partial.len()).is_some() && versions.nth(partial.len() + 1).is_some() {
             let version = versions.nth(partial.len()).unwrap();
diff --git a/src/semver.rs b/src/semver.rs
new file mode 100644
index 0000000000..0f8b537402
--- /dev/null
+++ b/src/semver.rs
@@ -0,0 +1,98 @@
+use versions::{Mess, Versioning};
+
+/// splits a version number into an optional prefix and the remaining version string
+pub fn split_version_prefix(version: &str) -> (String, String) {
+    version
+        .char_indices()
+        .find_map(|(i, c)| {
+            if c.is_ascii_digit() {
+                if i == 0 {
+                    return Some(i);
+                }
+                // If the previous char is a delimiter or 'v', we found a split point.
+                let prev_char = version.chars().nth(i - 1).unwrap();
+                if ['-', '_', '/', '.', 'v', 'V'].contains(&prev_char) {
+                    return Some(i);
+                }
+            }
+            None
+        })
+        .map_or_else(
+            || ("".into(), version.into()),
+            |i| {
+                let (prefix, version) = version.split_at(i);
+                (prefix.into(), version.into())
+            },
+        )
+}
+
+/// split a version number into chunks
+/// given v: "1.2-3a4" return ["1", ".2", "-3a4"]
+pub fn chunkify_version(v: &str) -> Vec<String> {
+    fn chunkify(m: &Mess, sep0: &str, chunks: &mut Vec<String>) {
+        for (i, chunk) in m.chunks.iter().enumerate() {
+            let sep = if i == 0 { sep0 } else { "." };
+            chunks.push(format!("{sep}{chunk}"));
+        }
+        if let Some((next_sep, next_mess)) = &m.next {
+            chunkify(next_mess, next_sep.to_string().as_ref(), chunks)
+        }
+    }
+
+    let mut chunks = vec![];
+    // don't parse "latest", otherwise bump from latest to any version would have one chunk only
+    if v != "latest" {
+        if let Some(v) = Versioning::new(v) {
+            let m = match v {
+                Versioning::Ideal(sem_ver) => sem_ver.to_mess(),
+                Versioning::General(version) => version.to_mess(),
+                Versioning::Complex(mess) => mess,
+            };
+            chunkify(&m, "", &mut chunks);
+        }
+    }
+    chunks
+}
+
+#[cfg(test)]
+mod tests {
+    use super::{chunkify_version, split_version_prefix};
+
+    #[test]
+    fn test_split_version_prefix() {
+        assert_eq!(split_version_prefix("latest"), ("".into(), "latest".into()));
+        assert_eq!(split_version_prefix("v1.2.3"), ("v".into(), "1.2.3".into()));
+        assert_eq!(
+            split_version_prefix("mountpoint-s3-v1.2.3-5_beta.5"),
+            ("mountpoint-s3-v".into(), "1.2.3-5_beta.5".into())
+        );
+        assert_eq!(
+            split_version_prefix("cli/1.2.3"),
+            ("cli/".into(), "1.2.3".into())
+        );
+        assert_eq!(
+            split_version_prefix("temurin-17.0.7+7"),
+            ("temurin-".into(), "17.0.7+7".into())
+        );
+        assert_eq!(split_version_prefix("1.2"), ("".into(), "1.2".into()));
+        assert_eq!(
+            split_version_prefix("2:1.2.1"),
+            ("".into(), "2:1.2.1".into())
+        );
+        assert_eq!(
+            split_version_prefix("2025-05-17"),
+            ("".into(), "2025-05-17".into())
+        );
+    }
+
+    #[test]
+    fn test_chunkify_version() {
+        assert_eq!(chunkify_version("1.2-3a4"), vec!["1", ".2", "-3a4"]);
+        assert_eq!(chunkify_version("latest"), Vec::<String>::new());
+        assert_eq!(chunkify_version("1.0.0"), vec!["1", ".0", ".0"]);
+        assert_eq!(
+            chunkify_version("2.3.4-beta"),
+            vec!["2", ".3", ".4", "-beta"]
+        );
+    }
+}
diff --git a/src/toolset/outdated_info.rs b/src/toolset/outdated_info.rs
index eeee934eb3..e5ca47820a 100644
--- a/src/toolset/outdated_info.rs
+++ b/src/toolset/outdated_info.rs
@@ -1,3 +1,4 @@
+use crate::semver::{chunkify_version, split_version_prefix};
 use crate::toolset;
 use crate::toolset::{ToolRequest, ToolSource, ToolVersion};
 use crate::{Result, config::Config};
@@ -7,7 +8,7 @@ use std::{
     sync::Arc,
 };
 use tabled::Tabled;
-use versions::{Mess, Version, Versioning};
+use versions::Version;
 
 #[derive(Debug, Serialize, Clone, Tabled)]
 pub struct OutdatedInfo {
@@ -55,11 +56,10 @@ impl OutdatedInfo {
     ) -> eyre::Result<Option<Self>> {
         let t = tv.backend()?;
         // prefix is something like "temurin-" or "corretto-"
-        let prefix = xx::regex!(r"^[a-zA-Z-]+-")
-            .find(&tv.request.version())
-            .map(|m| m.as_str().to_string());
+        let (prefix, _) = split_version_prefix(&tv.request.version());
         let latest_result = if bump {
-            t.latest_version(config, prefix.clone()).await
+            t.latest_version(config, Some(prefix.clone()).filter(|s| !s.is_empty()))
+                .await
         } else {
             tv.latest_version(config).await.map(Option::from)
         };
@@ -84,7 +84,6 @@ impl OutdatedInfo {
             return Ok(None);
         }
         if bump {
-            let prefix = prefix.unwrap_or_default();
             let old = oi.tool_version.request.version();
             let old = old.strip_prefix(&prefix).unwrap_or_default();
             let new = oi.latest.strip_prefix(&prefix).unwrap_or_default();
@@ -198,34 +197,6 @@ fn check_semver_bump(old: &str, new: &str) -> Option<String> {
     }
 }
 
-/// split a version number into chunks
-/// given v: "1.2-3a4" return ["1", ".2", "-3", "a4"]
-fn chunkify_version(v: &str) -> Vec<String> {
-    fn chunkify(m: &Mess, sep0: &str, chunks: &mut Vec<String>) {
-        for (i, chunk) in m.chunks.iter().enumerate() {
-            let sep = if i == 0 { sep0 } else { "." };
-            chunks.push(format!("{sep}{chunk}"));
-        }
-        if let Some((next_sep, next_mess)) = &m.next {
-            chunkify(next_mess, next_sep.to_string().as_ref(), chunks)
-        }
-    }
-
-    let mut chunks = vec![];
-    // don't parse "latest", otherwise bump from latest to any version would have one chunk only
-    if v != "latest" {
-        if let Some(v) = Versioning::new(v) {
-            let m = match v {
-                Versioning::Ideal(sem_ver) => sem_ver.to_mess(),
-                Versioning::General(version) => version.to_mess(),
-                Versioning::Complex(mess) => mess,
-            };
-            chunkify(&m, "", &mut chunks);
-        }
-    }
-    chunks
-}
-
 pub fn is_outdated_version(current: &str, latest: &str) -> bool {
     if let (Some(c), Some(l)) = (Version::new(current), Version::new(latest)) {
         c.lt(&l)