diff --git a/cmd/download.go b/cmd/download.go
index 9e5575a..812bb9b 100644
--- a/cmd/download.go
+++ b/cmd/download.go
@@ -3,10 +3,12 @@ package cmd
 import (
 	"fmt"
 	"log"
+	"slices"
 	"strings"
 	"time"
 
 	"github.com/cavaliergopher/grab/v3"
+	"github.com/hashicorp/go-version"
 	"github.com/schollz/progressbar/v3"
 	"github.com/spf13/cobra"
 	"github.com/timsutton/speedwagon/util"
@@ -80,26 +82,60 @@ working directory, named '<name of runtime>.(dmg|pkg)'.`,
 // 3. bool: whether auth is required
 func findMatchingRuntime(runtimeName string, data util.DVTDownloadablePlist) (string, string, bool) {
 
-	var runtimeFilename string
-	var runtimeUrl string
-	authRequired := false
+	var matchingRuntimes []util.PlatformDownloadable
+	var matchedRuntime util.PlatformDownloadable
 
-	foundMatchingRuntime := false
 	for _, v := range data.Downloadables {
 		if strings.HasPrefix(v.Name, runtimeName) {
-			foundMatchingRuntime = true
-			runtimeFilename = v.Name + ".dmg"
-			runtimeUrl = v.Source
+
+			foundRuntime := util.PlatformDownloadable{
+				Identifier: v.Identifier,
+				Source:     v.Source,
+				Name:       v.Name,
+				Platform:   v.Platform,
+			}
+
+			ver, _ := version.NewVersion(v.Version)
+			foundRuntime.Version = *ver
+
 			if v.Authentication != "" {
-				authRequired = true
+				foundRuntime.AuthRequired = true
 			}
+			foundRuntime.DownloadFileName = v.Name + ".dmg"
+			matchingRuntimes = append(matchingRuntimes, foundRuntime)
 		}
-		if foundMatchingRuntime {
-			break
-		}
 	}
 
-	return runtimeFilename, runtimeUrl, authRequired
+	// TODO: If there's 'Simulator' somewhere in the provided name, just try and match an exact slice elem
+	// and bypass the
+	// if strings.Contains(runtimeName, "Simulator") {
+
+	// }
+
+	// If there are multiple matches, take the highest-versioned one
+	if len(matchingRuntimes) > 1 {
+		slices.SortFunc(matchingRuntimes, func(a, b util.PlatformDownloadable) int {
+			return a.Version.Compare(&b.Version)
+		})
+		matchedRuntime = matchingRuntimes[len(matchingRuntimes)-1]
+	}
+
+	idx := slices.IndexFunc(matchingRuntimes,
+		func(r util.PlatformDownloadable) bool {
+			// Every entry contains the words 'Simulator' or 'Simulator Runtime', and we
+			// only care about the words leading up to that
+			normalizedName := strings.Split(r.Name, " Simulator")[0]
+			return normalizedName == runtimeName
+		})
+	if idx >= 0 {
+		matchedRuntime = matchingRuntimes[idx]
+	}
+
+	fmt.Println(matchedRuntime)
+
+	return matchedRuntime.DownloadFileName,
+		matchedRuntime.Source,
+		matchedRuntime.AuthRequired
 }
 
 func init() {
diff --git a/go.mod b/go.mod
index f403418..981c832 100644
--- a/go.mod
+++ b/go.mod
@@ -4,6 +4,7 @@ go 1.19
 
 require (
 	github.com/dustin/go-humanize v1.0.1
+	github.com/hashicorp/go-version v1.6.0
 	github.com/jedib0t/go-pretty/v6 v6.4.9
 	github.com/schollz/progressbar/v3 v3.14.1
 	github.com/spf13/cobra v1.8.0
@@ -21,7 +22,7 @@ require (
 require (
 	github.com/cavaliergopher/grab/v3 v3.0.1
 	github.com/inconshreveable/mousetrap v1.1.0 // indirect
-	github.com/mattn/go-runewidth v0.0.14 // indirect
+	github.com/mattn/go-runewidth v0.0.15 // indirect
 	github.com/rivo/uniseg v0.4.4 // indirect
 	github.com/spf13/pflag v1.0.5 // indirect
 	github.com/stretchr/testify v1.8.4
diff --git a/go.sum b/go.sum
index f6dcf84..dbdc226 100644
--- a/go.sum
+++ b/go.sum
@@ -6,6 +6,8 @@ github.com/davecgh/go-spew v1.1.1 h1:vj9j/u1bqnvCEfJOwUhtlOARqs3+rkHYY13jYWTU97c
 github.com/davecgh/go-spew v1.1.1/go.mod h1:J7Y8YcW2NihsgmVo/mv3lAwl/skON4iLHjSsI+c5H38=
 github.com/dustin/go-humanize v1.0.1 h1:GzkhY7T5VNhEkwH0PVJgjz+fX1rhBrR7pRT3mDkpeCY=
 github.com/dustin/go-humanize v1.0.1/go.mod h1:Mu1zIs6XwVuF/gI1OepvI0qD18qycQx+mFykh5fBlto=
+github.com/hashicorp/go-version v1.6.0 h1:feTTfFNnjP967rlCxM/I9g701jU+RN74YKx2mOkIeek=
+github.com/hashicorp/go-version v1.6.0/go.mod h1:fltr4n8CU8Ke44wwGCBoEymUuxUHl09ZGVZPK5anwXA=
 github.com/inconshreveable/mousetrap v1.1.0 h1:wN+x4NVGpMsO7ErUn/mUI3vEoE6Jt13X2s0bqwp9tc8=
 github.com/inconshreveable/mousetrap v1.1.0/go.mod h1:vpF70FUmC8bwa3OWnCshd2FqLfsEA9PFc4w1p2J65bw=
 github.com/jedib0t/go-pretty/v6 v6.4.9 h1:vZ6bjGg2eBSrJn365qlxGcaWu09Id+LHtrfDWlB2Usc=
@@ -14,8 +16,8 @@ github.com/jessevdk/go-flags v1.4.0/go.mod h1:4FA24M0QyGHXBuZZK/XkWh8h0e1EYbRYJS
 github.com/k0kubun/go-ansi v0.0.0-20180517002512-3bf9e2903213/go.mod h1:vNUNkEQ1e29fT/6vq2aBdFsgNPmy8qMdSay1npru+Sw=
 github.com/mattn/go-isatty v0.0.20/go.mod h1:W+V8PltTTMOvKvAeJH7IuucS94S2C6jfK/D7dTCTo3Y=
 github.com/mattn/go-runewidth v0.0.13/go.mod h1:Jdepj2loyihRzMpdS35Xk/zdY8IAYHsh153qUoGf23w=
-github.com/mattn/go-runewidth v0.0.14 h1:+xnbZSEeDbOIg5/mE6JF0w6n9duR1l3/WmbinWVwUuU=
-github.com/mattn/go-runewidth v0.0.14/go.mod h1:Jdepj2loyihRzMpdS35Xk/zdY8IAYHsh153qUoGf23w=
+github.com/mattn/go-runewidth v0.0.15 h1:UNAjwbU9l54TA3KzvqLGxwWjHmMgBUVhBiTjelZgg3U=
+github.com/mattn/go-runewidth v0.0.15/go.mod h1:Jdepj2loyihRzMpdS35Xk/zdY8IAYHsh153qUoGf23w=
 github.com/mitchellh/colorstring v0.0.0-20190213212951-d06e56a500db h1:62I3jR2EmQ4l5rM/4FEfDWcRD+abF5XlKShorW5LRoQ=
 github.com/mitchellh/colorstring v0.0.0-20190213212951-d06e56a500db/go.mod h1:l0dey0ia/Uv7NcFFVbCLtqEBQbrT4OCwCSKTEv6enCw=
 github.com/pkg/profile v1.6.0/go.mod h1:qBsxPvzyUincmltOk6iyRVxHYg4adc0OFOv72ZdLa18=
diff --git a/util/dvt.go b/util/dvt.go
index aa95144..dd21a19 100644
--- a/util/dvt.go
+++ b/util/dvt.go
@@ -8,6 +8,7 @@ import (
 	"os"
 	"path/filepath"
 
+	"github.com/hashicorp/go-version"
 	"howett.net/plist"
 )
 
@@ -62,6 +63,16 @@ type DVTDownloadablePlist struct {
 	Version string `plist:"version"`
 }
 
+type PlatformDownloadable struct {
+	Name             string
+	Platform         string
+	Identifier       string
+	Version          version.Version
+	Source           string
+	DownloadFileName string
+	AuthRequired     bool
+}
+
 func RefreshDVTMetadata() {
 	file, err := os.Create(DVTCacheFilePath())
 	if err != nil {