diff --git a/.github/workflows/nightly.yml b/.github/workflows/nightly.yml
new file mode 100644
index 000000000..86a3915e6
--- /dev/null
+++ b/.github/workflows/nightly.yml
@@ -0,0 +1,44 @@
+name: Nightly Release
+
+on:
+  schedule:
+    - cron: "0 6 * * *" # 06:00 UTC daily
+  workflow_dispatch:
+
+permissions:
+  contents: write
+
+concurrency:
+  group: nightly-release-${{ github.ref }}
+  cancel-in-progress: true
+jobs:
+  create-nightly-tag:
+    runs-on: ubuntu-latest
+    steps:
+      - name: Generate token
+        id: app-token
+        uses: actions/create-github-app-token@v3.0.0
+        with:
+          app-id: ${{ secrets.HOMEBREW_TAP_APP_ID }}
+          private-key: ${{ secrets.HOMEBREW_TAP_APP_PRIVATE_KEY }}
+          owner: ${{ github.repository_owner }}
+          repositories: cli
+
+      - uses: actions/checkout@v6
+        with:
+          fetch-depth: 0
+          token: ${{ steps.app-token.outputs.token }}
+
+      - name: Create nightly tag
+        run: |
+          TAG=$(scripts/create-nightly-tag.sh)
+          EXIT_CODE=$?
+          if [ "$EXIT_CODE" -eq 2 ]; then
+            echo "Skipping — no new nightly needed."
+            exit 0
+          elif [ "$EXIT_CODE" -ne 0 ] || [ -z "$TAG" ]; then
+            echo "::error::Failed to generate nightly tag"
+            exit 1
+          fi
+          git tag "$TAG"
+          git push origin "$TAG"
diff --git a/.github/workflows/release.yml b/.github/workflows/release.yml
index 99b19b3f4..d66351eca 100644
--- a/.github/workflows/release.yml
+++ b/.github/workflows/release.yml
@@ -30,7 +30,18 @@ jobs:
             homebrew-tap
             scoop-bucket
 
+      - name: Detect release type
+        id: release-type
+        run: |
+          VERSION="${GITHUB_REF_NAME#v}"
+          if [[ "$VERSION" == *-* ]]; then
+            echo "prerelease=true" >> "$GITHUB_OUTPUT"
+          else
+            echo "prerelease=false" >> "$GITHUB_OUTPUT"
+          fi
+
       - name: Extract release notes from CHANGELOG.md
+        if: steps.release-type.outputs.prerelease == 'false'
         run: |
           VERSION="${GITHUB_REF_NAME#v}"
           awk -v ver="$VERSION" 'BEGIN{header="^## \\[" ver "\\]"} $0 ~ header{found=1; next} /^## \[/{if(found) exit} found{print}' CHANGELOG.md > "$RUNNER_TEMP/release_notes.md"
@@ -39,6 +50,23 @@ jobs:
             exit 1
           fi
 
+      - name: Generate nightly release notes
+        if: steps.release-type.outputs.prerelease == 'true'
+        run: |
+          LAST_NIGHTLY=$(git tag -l 'v*-nightly.*' --sort=-creatordate | grep -v "^${GITHUB_REF_NAME}$" | head -1)
+          if [ -n "$LAST_NIGHTLY" ]; then
+            BASE_TAG="$LAST_NIGHTLY"
+          else
+            BASE_TAG=$(git describe --tags --abbrev=0 --match 'v[0-9]*' --exclude '*-*' HEAD 2>/dev/null || echo "")
+          fi
+          echo "## Nightly Build (${GITHUB_REF_NAME})" > "$RUNNER_TEMP/release_notes.md"
+          echo "" >> "$RUNNER_TEMP/release_notes.md"
+          if [ -n "$BASE_TAG" ]; then
+            echo "Changes since ${BASE_TAG}:" >> "$RUNNER_TEMP/release_notes.md"
+            echo "" >> "$RUNNER_TEMP/release_notes.md"
+            git log --oneline "${BASE_TAG}..HEAD" --no-merges >> "$RUNNER_TEMP/release_notes.md"
+          fi
+
       - name: Run GoReleaser
         uses: goreleaser/goreleaser-action@v7
         with:
diff --git a/.goreleaser.yaml b/.goreleaser.yaml
index 0191ad1b0..2d88597e5 100644
--- a/.goreleaser.yaml
+++ b/.goreleaser.yaml
@@ -66,6 +66,8 @@ archives:
 checksum:
   name_template: "checksums.txt"
 
+release:
+  prerelease: auto
 
 scoops:
   - repository:
@@ -75,6 +77,7 @@ scoops:
     homepage: "https://github.com/entireio/cli"
     description: "CLI for Entire"
     license: MIT
+    skip_upload: auto
 
 homebrew_casks:
   - name: entire
@@ -91,9 +94,30 @@ homebrew_casks:
       bash: "completions/entire.bash"
       zsh: "completions/entire.zsh"
       fish: "completions/entire.fish"
+    conflicts:
+      - cask: entire@nightly
+    skip_upload: auto
+
+  - name: entire@nightly
+    repository:
+      owner: entireio
+      name: homebrew-tap
+      token: "{{ .Env.TAP_GITHUB_TOKEN }}"
+    directory: Casks
+    homepage: "https://github.com/entireio/cli"
+    description: "CLI for Entire (nightly build)"
+    binaries:
+      - entire
+    completions:
+      bash: "completions/entire.bash"
+      zsh: "completions/entire.zsh"
+      fish: "completions/entire.fish"
+    conflicts:
+      - cask: entire
+    skip_upload: "{{ if not .Prerelease }}true{{ end }}"
 
 announce:
   discord:
-    enabled: '{{ and (isEnvSet "DISCORD_WEBHOOK_ID") (isEnvSet "DISCORD_WEBHOOK_TOKEN") }}'
+    enabled: '{{ and (not .Prerelease) (isEnvSet "DISCORD_WEBHOOK_ID") (isEnvSet "DISCORD_WEBHOOK_TOKEN") }}'
     message_template: "Beep, boop. **Entire CLI {{ .Tag }}** is out!\n\n{{ .ReleaseURL }}\n\nSee https://docs.entire.io/cli/installation for help installing and updating."
     author: "Entire"
diff --git a/cmd/entire/cli/versioncheck/types.go b/cmd/entire/cli/versioncheck/types.go
index d4773416d..6b02e90e2 100644
--- a/cmd/entire/cli/versioncheck/types.go
+++ b/cmd/entire/cli/versioncheck/types.go
@@ -13,10 +13,13 @@ type GitHubRelease struct {
 	Prerelease bool   `json:"prerelease"`
 }
 
-// githubAPIURL is the GitHub API endpoint for fetching the latest release.
+// githubAPIURL is the GitHub API endpoint for fetching the latest stable release.
 // This is a var (not const) to allow overriding in tests.
 var githubAPIURL = "https://api.github.com/repos/entireio/cli/releases/latest"
 
+// githubReleasesURL is the GitHub API endpoint for listing releases (used for nightly checks).
+var githubReleasesURL = "https://api.github.com/repos/entireio/cli/releases"
+
 const (
 	// checkInterval is the duration between version checks.
 	checkInterval = 24 * time.Hour
diff --git a/cmd/entire/cli/versioncheck/versioncheck.go b/cmd/entire/cli/versioncheck/versioncheck.go
index df989b3cf..e7568cfb0 100644
--- a/cmd/entire/cli/versioncheck/versioncheck.go
+++ b/cmd/entire/cli/versioncheck/versioncheck.go
@@ -13,6 +13,7 @@ import (
 	"time"
 
 	"github.com/entireio/cli/cmd/entire/cli/logging"
+	"github.com/entireio/cli/cmd/entire/cli/versioninfo"
 	"golang.org/x/mod/semver"
 )
 
@@ -42,8 +43,13 @@ func CheckAndNotify(ctx context.Context, w io.Writer, currentVersion string) {
 		return
 	}
 
-	// Fetch the latest version from GitHub API
-	latestVersion, err := fetchLatestVersion(ctx)
+	// Fetch the latest version from the appropriate channel
+	var latestVersion string
+	if isNightly(currentVersion) {
+		latestVersion, err = fetchLatestNightlyVersion(ctx)
+	} else {
+		latestVersion, err = fetchLatestVersion(ctx)
+	}
 
 	// Always update cache to avoid retrying on every CLI invocation
 	cache.LastCheckTime = time.Now()
@@ -200,6 +206,57 @@ func fetchLatestVersion(ctx context.Context) (string, error) {
 	return version, nil
 }
 
+// isNightly returns true if the version string is a nightly build.
+func isNightly(version string) bool {
+	if !strings.HasPrefix(version, "v") {
+		version = "v" + version
+	}
+	return strings.Contains(semver.Prerelease(version), "nightly")
+}
+
+// fetchLatestNightlyVersion fetches the latest nightly version from the GitHub releases list.
+func fetchLatestNightlyVersion(ctx context.Context) (string, error) {
+	ctx, cancel := context.WithTimeout(ctx, httpTimeout)
+	defer cancel()
+
+	req, err := http.NewRequestWithContext(ctx, http.MethodGet, githubReleasesURL+"?per_page=20", nil)
+	if err != nil {
+		return "", fmt.Errorf("creating request: %w", err)
+	}
+
+	req.Header.Set("Accept", "application/vnd.github+json")
+	req.Header.Set("User-Agent", "entire-cli/"+versioninfo.Version)
+
+	client := &http.Client{}
+	resp, err := client.Do(req)
+	if err != nil {
+		return "", fmt.Errorf("fetching releases: %w", err)
+	}
+	defer resp.Body.Close()
+
+	if resp.StatusCode != http.StatusOK {
+		return "", fmt.Errorf("unexpected status code: %d", resp.StatusCode)
+	}
+
+	body, err := io.ReadAll(io.LimitReader(resp.Body, 1<<20))
+	if err != nil {
+		return "", fmt.Errorf("reading response: %w", err)
+	}
+
+	var releases []GitHubRelease
+	if err := json.Unmarshal(body, &releases); err != nil {
+		return "", fmt.Errorf("parsing JSON: %w", err)
+	}
+
+	for _, r := range releases {
+		if r.Prerelease && strings.Contains(r.TagName, "-nightly.") {
+			return r.TagName, nil
+		}
+	}
+
+	return "", errors.New("no nightly release found")
+}
+
 // parseGitHubRelease parses the GitHub API response and extracts the latest stable version.
 // Filters out prerelease versions.
 func parseGitHubRelease(body []byte) (string, error) {
diff --git a/cmd/entire/cli/versioncheck/versioncheck_test.go b/cmd/entire/cli/versioncheck/versioncheck_test.go
index 42dea19c9..26fabdf0b 100644
--- a/cmd/entire/cli/versioncheck/versioncheck_test.go
+++ b/cmd/entire/cli/versioncheck/versioncheck_test.go
@@ -40,6 +40,11 @@ func TestIsOutdated(t *testing.T) {
 		{"1.0.0-rc1", "1.0.0", true, "prerelease in current"},
 		{"1.0.0", "1.0.1-rc1", true, "prerelease in latest is still newer"},
 		{"1.0.0-dev-xxx", "1.0.1", false, "dev build skips version check"},
+
+		// Nightly-vs-nightly comparisons (same channel)
+		{"0.5.3-nightly.202604051159.abc1234", "0.5.3-nightly.202604061200.def5678", true, "older nightly is outdated by newer nightly"},
+		{"0.5.3-nightly.202604061200.def5678", "0.5.3-nightly.202604051159.abc1234", false, "newer nightly is not outdated by older nightly"},
+		{"0.5.3-nightly.202604061200.abc1234", "0.5.3-nightly.202604061200.abc1234", false, "same nightly is not outdated"},
 	}
 
 	for _, tt := range tests {
@@ -52,6 +57,77 @@ func TestIsOutdated(t *testing.T) {
 	}
 }
 
+func TestIsNightly(t *testing.T) {
+	t.Parallel()
+	tests := []struct {
+		version string
+		want    bool
+	}{
+		{"0.5.3-nightly.202604061200.abc1234", true},
+		{"v0.5.3-nightly.202604061200.abc1234", true},
+		{"1.0.0", false},
+		{"v1.0.0", false},
+		{"1.0.0-rc1", false},
+		{"1.0.0-dev-xxx", false},
+		{"dev", false},
+	}
+	for _, tt := range tests {
+		t.Run(tt.version, func(t *testing.T) {
+			t.Parallel()
+			if got := isNightly(tt.version); got != tt.want {
+				t.Errorf("isNightly(%q) = %v, want %v", tt.version, got, tt.want)
+			}
+		})
+	}
+}
+
+func TestFetchLatestNightlyVersion(t *testing.T) {
+	server := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, _ *http.Request) {
+		releases := []GitHubRelease{
+			{TagName: "v0.5.4", Prerelease: false},
+			{TagName: "v0.5.4-nightly.202604061200.abc1234", Prerelease: true},
+			{TagName: "v0.5.4-nightly.202604051159.def5678", Prerelease: true},
+		}
+		w.Header().Set("Content-Type", "application/json")
+		//nolint:errcheck // test helper
+		json.NewEncoder(w).Encode(releases)
+	}))
+	defer server.Close()
+
+	original := githubReleasesURL
+	githubReleasesURL = server.URL
+	t.Cleanup(func() { githubReleasesURL = original })
+
+	version, err := fetchLatestNightlyVersion(context.Background())
+	if err != nil {
+		t.Fatalf("fetchLatestNightlyVersion() error = %v", err)
+	}
+	if version != "v0.5.4-nightly.202604061200.abc1234" {
+		t.Errorf("fetchLatestNightlyVersion() = %q, want v0.5.4-nightly.202604061200.abc1234", version)
+	}
+}
+
+func TestFetchLatestNightlyVersion_NoNightlies(t *testing.T) {
+	server := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, _ *http.Request) {
+		releases := []GitHubRelease{
+			{TagName: "v0.5.4", Prerelease: false},
+		}
+		w.Header().Set("Content-Type", "application/json")
+		//nolint:errcheck // test helper
+		json.NewEncoder(w).Encode(releases)
+	}))
+	defer server.Close()
+
+	original := githubReleasesURL
+	githubReleasesURL = server.URL
+	t.Cleanup(func() { githubReleasesURL = original })
+
+	_, err := fetchLatestNightlyVersion(context.Background())
+	if err == nil {
+		t.Fatal("fetchLatestNightlyVersion() expected error when no nightlies, got nil")
+	}
+}
+
 func TestCacheReadWrite(t *testing.T) {
 	// Create a temporary directory for the test
 	tmpDir := t.TempDir()
diff --git a/mise-tasks/release b/mise-tasks/release
new file mode 100755
index 000000000..57b054746
--- /dev/null
+++ b/mise-tasks/release
@@ -0,0 +1,45 @@
+#!/bin/sh
+#MISE description="Create stable + nightly release tags and push them (usage: mise run release vX.X.X)"
+set -eu
+
+VERSION="${1:-}"
+if [ -z "$VERSION" ]; then
+  echo "Usage: mise run release vX.X.X"
+  exit 1
+fi
+
+# Ensure version starts with v
+case "$VERSION" in
+  v*) ;;
+  *) VERSION="v${VERSION}" ;;
+esac
+
+# Validate semver format (vMAJOR.MINOR.PATCH)
+if ! echo "$VERSION" | grep -qE '^v[0-9]+\.[0-9]+\.[0-9]+$'; then
+  echo "Error: invalid version format '${VERSION}', expected vMAJOR.MINOR.PATCH"
+  exit 1
+fi
+
+# Ensure working tree is clean
+if [ -n "$(git status --porcelain)" ]; then
+  echo "Error: working tree is not clean, commit or stash changes first"
+  exit 1
+fi
+
+# Create stable tag first so the nightly script can find it
+git tag "$VERSION"
+echo "Created tag ${VERSION}"
+
+# Generate and create nightly tag if possible
+NIGHTLY_TAG=$(scripts/create-nightly-tag.sh) || true
+
+git push origin "$VERSION"
+echo "Pushed tag ${VERSION}"
+
+if [ -n "$NIGHTLY_TAG" ]; then
+  git tag "$NIGHTLY_TAG"
+  echo "Created tag ${NIGHTLY_TAG}"
+  git push origin "$NIGHTLY_TAG"
+fi
+echo ""
+echo "Done. Release workflows will start automatically."
diff --git a/scripts/create-nightly-tag.sh b/scripts/create-nightly-tag.sh
new file mode 100755
index 000000000..8ab46b781
--- /dev/null
+++ b/scripts/create-nightly-tag.sh
@@ -0,0 +1,41 @@
+#!/usr/bin/env bash
+set -euo pipefail
+
+# Calculate the next nightly release tag based on the latest stable tag and HEAD.
+# Outputs the tag name to stdout, or exits 0 silently if a nightly already exists for HEAD.
+#
+# Tag format: v<major>.<minor>.<patch+1>-nightly.<YYYYMMDDhhmm>.<short-commit>
+# Usage: scripts/create-nightly-tag.sh
+
+SHORT_COMMIT=$(git rev-parse --short HEAD)
+
+# Skip if a nightly tag already exists for this commit
+if git tag -l "v*-nightly.*.${SHORT_COMMIT}" | grep -q .; then
+  echo "Nightly tag already exists for commit ${SHORT_COMMIT}, skipping." >&2
+  exit 2
+fi
+
+# Find the latest stable version tag (exclude prereleases)
+LATEST_STABLE=$(git describe --tags --abbrev=0 --match 'v[0-9]*' --exclude '*-*' 2>/dev/null)
+if [ -z "$LATEST_STABLE" ]; then
+  echo "::error::No stable version tag found" >&2
+  exit 1
+fi
+
+# Bump patch version: v0.5.4 → v0.5.5
+MAJOR=$(echo "$LATEST_STABLE" | sed 's/^v//' | cut -d. -f1)
+MINOR=$(echo "$LATEST_STABLE" | sed 's/^v//' | cut -d. -f2)
+PATCH=$(echo "$LATEST_STABLE" | sed 's/^v//' | cut -d. -f3)
+NEXT_PATCH=$((PATCH + 1))
+NIGHTLY_VERSION="v${MAJOR}.${MINOR}.${NEXT_PATCH}"
+
+DATE=$(TZ=UTC0 date +%Y%m%d%H%M)
+TAG="${NIGHTLY_VERSION}-nightly.${DATE}.${SHORT_COMMIT}"
+
+# Skip if this exact tag already exists
+if git rev-parse "${TAG}" >/dev/null 2>&1; then
+  echo "Tag ${TAG} already exists, skipping." >&2
+  exit 2
+fi
+
+echo "${TAG}"