diff --git a/internal/helm/repository.go b/internal/helm/repository.go
index 2e555369..762a4cb5 100644
--- a/internal/helm/repository.go
+++ b/internal/helm/repository.go
@@ -98,11 +98,7 @@ func (r *ChartRepository) Get(name, version string) (*repo.ChartVersion, error)
 		if err != nil {
 			continue
 		}
-		// NB: given the entries are already sorted in LoadIndex,
-		// there is a high probability the first match would be
-		// the right match to return. However, due to the fact that
-		// we use a different semver package than Helm does, we still
-		// need to sort it by our own rules.
+
 		if match != nil && !match(v) {
 			continue
 		}
@@ -112,7 +108,25 @@ func (r *ChartRepository) Get(name, version string) (*repo.ChartVersion, error)
 	if len(filteredVersions) == 0 {
 		return nil, fmt.Errorf("no chart version found for %s-%s", name, version)
 	}
-	sort.Sort(sort.Reverse(filteredVersions))
+
+	// Sort versions
+	sort.SliceStable(filteredVersions, func(i, j int) bool {
+		// Reverse
+		return !(func() bool {
+			left := filteredVersions[i]
+			right := filteredVersions[j]
+
+			if !left.EQ(right) {
+				return left.LT(right)
+			}
+
+			// Having chart creation timestamp at our disposal, we put package with the
+			// same version into a chronological order. This is especially important for
+			// versions that differ only by build metadata, because it is not considered
+			// a part of the comparable version in Semver
+			return lookup[left.String()].Created.Before(lookup[right.String()].Created)
+		})()
+	})
 
 	latest := filteredVersions[0]
 	if latestStable {
diff --git a/internal/helm/repository_test.go b/internal/helm/repository_test.go
index 884a3732..469186ad 100644
--- a/internal/helm/repository_test.go
+++ b/internal/helm/repository_test.go
@@ -23,6 +23,7 @@ import (
 	"reflect"
 	"strings"
 	"testing"
+	"time"
 
 	"helm.sh/helm/v3/pkg/chart"
 	"helm.sh/helm/v3/pkg/getter"
@@ -104,6 +105,11 @@ func TestChartRepository_Get(t *testing.T) {
 	i.Add(&chart.Metadata{Name: "chart", Version: "exact"}, "chart-exact.tgz", "http://example.com/charts", "sha256:1234567890")
 	i.Add(&chart.Metadata{Name: "chart", Version: "0.1.0"}, "chart-0.1.0.tgz", "http://example.com/charts", "sha256:1234567890abc")
 	i.Add(&chart.Metadata{Name: "chart", Version: "0.1.1"}, "chart-0.1.1.tgz", "http://example.com/charts", "sha256:1234567890abc")
+	i.Add(&chart.Metadata{Name: "chart", Version: "0.1.5+b.min.minute"}, "chart-0.1.5+b.min.minute.tgz", "http://example.com/charts", "sha256:1234567890abc")
+	i.Entries["chart"][len(i.Entries["chart"])-1].Created = time.Now().Add(-time.Minute)
+	i.Add(&chart.Metadata{Name: "chart", Version: "0.1.5+a.min.hour"}, "chart-0.1.5+a.min.hour.tgz", "http://example.com/charts", "sha256:1234567890abc")
+	i.Entries["chart"][len(i.Entries["chart"])-1].Created = time.Now().Add(-time.Hour)
+	i.Add(&chart.Metadata{Name: "chart", Version: "0.1.5+c.now"}, "chart-0.1.5+c.now.tgz", "http://example.com/charts", "sha256:1234567890abc")
 	i.Add(&chart.Metadata{Name: "chart", Version: "0.2.0"}, "chart-0.2.0.tgz", "http://example.com/charts", "sha256:1234567890abc")
 	i.Add(&chart.Metadata{Name: "chart", Version: "1.0.0"}, "chart-1.0.0.tgz", "http://example.com/charts", "sha256:1234567890abc")
 	i.Add(&chart.Metadata{Name: "chart", Version: "1.1.0-rc.1"}, "chart-1.1.0-rc.1.tgz", "http://example.com/charts", "sha256:1234567890abc")
@@ -152,6 +158,12 @@ func TestChartRepository_Get(t *testing.T) {
 			chartName: "non-existing",
 			wantErr:   true,
 		},
+		{
+			name:         "match newest if ambiguous",
+			chartName:    "chart",
+			chartVersion: "0.1.5",
+			wantVersion:  "0.1.5+c.now",
+		},
 	}
 
 	for _, tt := range tests {
diff --git a/pkg/git/checkout.go b/pkg/git/checkout.go
index 26a54f8b..103f49f5 100644
--- a/pkg/git/checkout.go
+++ b/pkg/git/checkout.go
@@ -19,6 +19,8 @@ package git
 import (
 	"context"
 	"fmt"
+	"sort"
+	"time"
 
 	"github.com/blang/semver/v4"
 	"github.com/go-git/go-git/v5"
@@ -189,7 +191,19 @@ func (c *CheckoutSemVer) Checkout(ctx context.Context, path, url string, auth tr
 	}
 
 	tags := make(map[string]string)
+	tagTimestamps := make(map[string]time.Time)
 	_ = repoTags.ForEach(func(t *plumbing.Reference) error {
+		revision := plumbing.Revision(t.Name().String())
+		hash, err := repo.ResolveRevision(revision)
+		if err != nil {
+			return fmt.Errorf("unable to resolve tag revision: %w", err)
+		}
+		commit, err := repo.CommitObject(*hash)
+		if err != nil {
+			return fmt.Errorf("unable to resolve commit of a tag revision: %w", err)
+		}
+		tagTimestamps[t.Name().Short()] = commit.Committer.When
+
 		tags[t.Name().Short()] = t.Strings()[1]
 		return nil
 	})
@@ -203,12 +217,25 @@ func (c *CheckoutSemVer) Checkout(ctx context.Context, path, url string, auth tr
 			svTags[v.String()] = tag
 		}
 	}
-
 	if len(svers) == 0 {
 		return nil, "", fmt.Errorf("no match found for semver: %s", c.semVer)
 	}
 
-	semver.Sort(svers)
+	// Sort versions
+	sort.SliceStable(svers, func(i, j int) bool {
+		left := svers[i]
+		right := svers[j]
+
+		if !left.EQ(right) {
+			return left.LT(right)
+		}
+
+		// Having tag target timestamps at our disposal, we further try to sort
+		// versions into a chronological order. This is especially important for
+		// versions that differ only by build metadata, because it is not considered
+		// a part of the comparable version in Semver
+		return tagTimestamps[left.String()].Before(tagTimestamps[right.String()])
+	})
 	v := svers[len(svers)-1]
 	t := svTags[v.String()]