diff --git a/cli/cmd/upgrade/upgrade.go b/cli/cmd/upgrade/upgrade.go
index d7805be3f289..06a17f7341bf 100644
--- a/cli/cmd/upgrade/upgrade.go
+++ b/cli/cmd/upgrade/upgrade.go
@@ -10,6 +10,7 @@ import (
 func UpgradeCmd(ch *cmdutil.Helper) *cobra.Command {
 	var version string
 	var nightly bool
+	var force bool
 
 	upgradeCmd := &cobra.Command{
 		Use:   "upgrade",
@@ -24,19 +25,20 @@ func UpgradeCmd(ch *cmdutil.Helper) *cobra.Command {
 				}
 				version = "v" + v.String()
 
-				return installscript.Install(cmd.Context(), version)
+				return installscript.Install(cmd.Context(), version, force)
 			}
 
 			if nightly {
-				return installscript.Install(cmd.Context(), "nightly")
+				return installscript.Install(cmd.Context(), "nightly", force)
 			}
 
-			return installscript.Install(cmd.Context(), "")
+			return installscript.Install(cmd.Context(), "", force)
 		},
 	}
 
 	upgradeCmd.Flags().StringVar(&version, "version", "", "Install a specific version of Rill")
 	upgradeCmd.Flags().BoolVar(&nightly, "nightly", false, "Install the latest nightly build")
+	upgradeCmd.Flags().BoolVar(&force, "force", false, "Reinstall even if the latest version is already installed")
 
 	return upgradeCmd
 }
diff --git a/cli/pkg/installscript/installscript.go b/cli/pkg/installscript/installscript.go
index a997405593f2..5431b8e67063 100644
--- a/cli/pkg/installscript/installscript.go
+++ b/cli/pkg/installscript/installscript.go
@@ -9,15 +9,19 @@ import (
 	"os/exec"
 )
 
-func Install(ctx context.Context, version string) error {
-	return execScript(ctx, version, "--version", version)
+func Install(ctx context.Context, version string, force bool) error {
+	var env []string
+	if force {
+		env = append(os.Environ(), "RILL_INSTALL_FORCE=1")
+	}
+	return execScript(ctx, version, env, "--version", version)
 }
 
 func Uninstall(ctx context.Context) error {
-	return execScript(ctx, "", "--uninstall")
+	return execScript(ctx, "", nil, "--uninstall")
 }
 
-func execScript(ctx context.Context, version string, args ...string) error {
+func execScript(ctx context.Context, version string, env []string, args ...string) error {
 	script, err := createScriptFile(ctx, version)
 	if err != nil {
 		return err
@@ -26,6 +30,7 @@ func execScript(ctx context.Context, version string, args ...string) error {
 
 	scriptArgs := append([]string{script}, args...)
 	cmd := exec.CommandContext(ctx, "/bin/sh", scriptArgs...)
+	cmd.Env = env
 	cmd.Stdin = os.Stdin
 	cmd.Stdout = os.Stdout
 	cmd.Stderr = os.Stderr
diff --git a/docs/docs/developers/get-started/install.md b/docs/docs/developers/get-started/install.md
index 2758ffbb3762..8aefcd710193 100644
--- a/docs/docs/developers/get-started/install.md
+++ b/docs/docs/developers/get-started/install.md
@@ -44,6 +44,11 @@ To ensure you're on the latest version of Rill and enjoying all of our newest fe
 rill upgrade
 ```
 
+If the latest version is already installed, the upgrade is skipped. To reinstall anyway, run `rill upgrade --force`, or set `RILL_INSTALL_FORCE=1` when using the installation script:
+```bash
+curl https://rill.sh | RILL_INSTALL_FORCE=1 sh
+```
+
 :::info What about Rill Cloud?
 
 Rill Cloud is always on the latest stable version of Rill. To check the latest version available, please see our [Releases](https://github.com/rilldata/rill/releases) page.
diff --git a/docs/docs/reference/cli/upgrade.md b/docs/docs/reference/cli/upgrade.md
index 1d8382b2c1c4..072ddc7cada7 100644
--- a/docs/docs/reference/cli/upgrade.md
+++ b/docs/docs/reference/cli/upgrade.md
@@ -13,6 +13,7 @@ rill upgrade [flags]
 ### Flags
 
 ```
+      --force            Reinstall even if the latest version is already installed
       --nightly          Install the latest nightly build
       --version string   Install a specific version of Rill
 ```
diff --git a/scripts/install.sh b/scripts/install.sh
index 063ad8fbaf83..ea0ba1136b26 100755
--- a/scripts/install.sh
+++ b/scripts/install.sh
@@ -62,11 +62,6 @@ sha256Verify() {
 # Download the binary and check the integrity using the SHA256 checksum
 downloadBinary() {
     CDN="cdn.rilldata.com"
-
-    LATEST_URL="https://${CDN}/rill/latest.txt"
-    if [ "${VERSION}" = "latest" ]; then
-        VERSION=$(curl --silent --show-error "${LATEST_URL}")
-    fi
     BINARY_URL="https://${CDN}/rill/${VERSION}/rill_${PLATFORM}.zip"
     CHECKSUM_URL="https://${CDN}/rill/${VERSION}/checksums.txt"
 
@@ -91,6 +86,24 @@ downloadBinary() {
     unzip -q "rill_${PLATFORM}.zip"
 }
 
+# Resolve 'latest' to a concrete version and exit if it is already installed.
+resolveLatestVersion() {
+    if [ "${VERSION}" != "latest" ]; then
+        return
+    fi
+    VERSION=$(curl --silent --show-error "https://cdn.rilldata.com/rill/latest.txt")
+
+    if [ -n "$RILL_INSTALL_FORCE" ] || ! [ -x "$INSTALL_DIR/rill" ]; then
+        return
+    fi
+    # Output format: 'rill version v0.90.3 (build commit: ... date: ...)'
+    INSTALLED_VERSION=$("$INSTALL_DIR"/rill version 2>/dev/null | cut -d' ' -f3) || true
+    if [ "$INSTALLED_VERSION" = "$VERSION" ]; then
+        printf "Rill %s is already installed. To reinstall, run 'rill upgrade --force' or set RILL_INSTALL_FORCE=1.\n" "$VERSION"
+        exit 0
+    fi
+}
+
 # Print install options
 printInstallOptions() {
     printf "\nWhere would you like to install rill?  (Default [1])\n\n"
@@ -298,6 +311,7 @@ installRill() {
     checkDependencies
     initPlatform
     resolveInstallDir
+    resolveLatestVersion
     initTmpDir
     downloadBinary
     installBinary