diff --git a/docs/admin/notifications.md b/docs/admin/notifications.md
index e4cd9a27b5f53..d4297fac455d8 100644
--- a/docs/admin/notifications.md
+++ b/docs/admin/notifications.md
@@ -77,9 +77,9 @@ can only be delivered to one method, and this method is configured globally with
 [`CODER_NOTIFICATIONS_METHOD`](https://coder.com/docs/reference/cli/server#--notifications-method)
 (default: `smtp`).
 
-Enterprise customers can configured which method to use for each of the
-supported [Events](#events); see the [Preferences](#preferences) section below
-for more details.
+Enterprise customers can configure which method to use for each of the supported
+[Events](#events); see the [Preferences](#preferences) section below for more
+details.
 
 ## SMTP (Email)
 
@@ -93,7 +93,7 @@ existing one.
 | :------: | --------------------------------- | ------------------------------------- | ----------- | ----------------------------------------- | ------------- |
 |    ✔️    | `--notifications-email-from`      | `CODER_NOTIFICATIONS_EMAIL_FROM`      | `string`    | The sender's address to use.              |               |
 |    ✔️    | `--notifications-email-smarthost` | `CODER_NOTIFICATIONS_EMAIL_SMARTHOST` | `host:port` | The SMTP relay to send messages through.  | localhost:587 |
-|    -️    | `--notifications-email-hello`     | `CODER_NOTIFICATIONS_EMAIL_HELLO`     | `string`    | The hostname identifying the SMTP server. | localhost     |
+|    ✔️    | `--notifications-email-hello`     | `CODER_NOTIFICATIONS_EMAIL_HELLO`     | `string`    | The hostname identifying the SMTP server. | localhost     |
 
 **Authentication Settings:**
 
@@ -252,6 +252,18 @@ To pause sending notifications, execute
 To resume sending notifications, execute
 [`coder notifications resume`](https://coder.com/docs/reference/cli/notifications_resume).
 
+## Troubleshooting
+
+If notifications are not being delivered, use the following methods to
+troubleshoot:
+
+1. Ensure notifications are being added to the `notification_messages` table
+2. Review any error messages in the `status_reason` column, should an error have
+   occurred
+3. Review the logs (search for the term `notifications`) for diagnostic
+   information<br> _If you do not see any relevant logs, set
+   `CODER_VERBOSE=true` or `--verbose` to output debug logs_
+
 ## Internals
 
 The notification system is built to operate concurrently in a single- or
@@ -288,5 +300,4 @@ messages._
   - after `CODER_NOTIFICATIONS_MAX_SEND_ATTEMPTS` is exceeded, it transitions to
     `permanent_failure`
 
-Diagnostic messages will be saved in the `notification_messages` table and will
-be logged, in the case of failure.
+See [Troubleshooting](#troubleshooting) above for more details.
diff --git a/docs/images/admin/notification-states.png b/docs/images/admin/notification-states.png
index cdd3de7ff0f91..f2fa0960bb876 100644
Binary files a/docs/images/admin/notification-states.png and b/docs/images/admin/notification-states.png differ
diff --git a/enterprise/coderd/coderdenttest/coderdenttest.go b/enterprise/coderd/coderdenttest/coderdenttest.go
index f5bfd05529fdd..d4a75451e003b 100644
--- a/enterprise/coderd/coderdenttest/coderdenttest.go
+++ b/enterprise/coderd/coderdenttest/coderdenttest.go
@@ -174,6 +174,10 @@ type LicenseOptions struct {
 	// ExpiresAt is the time at which the license will hard expire.
 	// ExpiresAt should always be greater then GraceAt.
 	ExpiresAt time.Time
+	// NotBefore is the time at which the license becomes valid. If set to the
+	// zero value, the `nbf` claim on the license is set to 1 minute in the
+	// past.
+	NotBefore time.Time
 	Features  license.Features
 }
 
@@ -195,6 +199,13 @@ func (opts *LicenseOptions) Valid(now time.Time) *LicenseOptions {
 	return opts
 }
 
+func (opts *LicenseOptions) FutureTerm(now time.Time) *LicenseOptions {
+	opts.NotBefore = now.Add(time.Hour * 24)
+	opts.ExpiresAt = now.Add(time.Hour * 24 * 60)
+	opts.GraceAt = now.Add(time.Hour * 24 * 53)
+	return opts
+}
+
 func (opts *LicenseOptions) UserLimit(limit int64) *LicenseOptions {
 	return opts.Feature(codersdk.FeatureUserLimit, limit)
 }
@@ -233,13 +244,16 @@ func GenerateLicense(t *testing.T, options LicenseOptions) string {
 	if options.GraceAt.IsZero() {
 		options.GraceAt = time.Now().Add(time.Hour)
 	}
+	if options.NotBefore.IsZero() {
+		options.NotBefore = time.Now().Add(-time.Minute)
+	}
 
 	c := &license.Claims{
 		RegisteredClaims: jwt.RegisteredClaims{
 			ID:        uuid.NewString(),
 			Issuer:    "test@testing.test",
 			ExpiresAt: jwt.NewNumericDate(options.ExpiresAt),
-			NotBefore: jwt.NewNumericDate(time.Now().Add(-time.Minute)),
+			NotBefore: jwt.NewNumericDate(options.NotBefore),
 			IssuedAt:  jwt.NewNumericDate(time.Now().Add(-time.Minute)),
 		},
 		LicenseExpires: jwt.NewNumericDate(options.GraceAt),
diff --git a/enterprise/coderd/license/license.go b/enterprise/coderd/license/license.go
index fdb177d753eae..6f0e827eb3320 100644
--- a/enterprise/coderd/license/license.go
+++ b/enterprise/coderd/license/license.go
@@ -100,6 +100,13 @@ func LicensesEntitlements(
 	//   'Entitlements' group as a whole.
 	for _, license := range licenses {
 		claims, err := ParseClaims(license.JWT, keys)
+		var vErr *jwt.ValidationError
+		if xerrors.As(err, &vErr) && vErr.Is(jwt.ErrTokenNotValidYet) {
+			// The license isn't valid yet.  We don't consider any entitlements contained in it, but
+			// it's also not an error.  Just skip it silently.  This can happen if an administrator
+			// uploads a license for a new term that hasn't started yet.
+			continue
+		}
 		if err != nil {
 			entitlements.Errors = append(entitlements.Errors,
 				fmt.Sprintf("Invalid license (%s) parsing claims: %s", license.UUID.String(), err.Error()))
@@ -287,6 +294,8 @@ var (
 	ErrInvalidVersion        = xerrors.New("license must be version 3")
 	ErrMissingKeyID          = xerrors.Errorf("JOSE header must contain %s", HeaderKeyID)
 	ErrMissingLicenseExpires = xerrors.New("license missing license_expires")
+	ErrMissingExp            = xerrors.New("exp claim missing or not parsable")
+	ErrMultipleIssues        = xerrors.New("license has multiple issues; contact support")
 )
 
 type Features map[codersdk.FeatureName]int64
@@ -336,7 +345,7 @@ func ParseRaw(l string, keys map[string]ed25519.PublicKey) (jwt.MapClaims, error
 	return nil, xerrors.New("unable to parse Claims")
 }
 
-// ParseClaims validates a database.License record, and if valid, returns the claims.  If
+// ParseClaims validates a raw JWT, and if valid, returns the claims.  If
 // unparsable or invalid, it returns an error
 func ParseClaims(rawJWT string, keys map[string]ed25519.PublicKey) (*Claims, error) {
 	tok, err := jwt.ParseWithClaims(
@@ -348,18 +357,53 @@ func ParseClaims(rawJWT string, keys map[string]ed25519.PublicKey) (*Claims, err
 	if err != nil {
 		return nil, err
 	}
-	if claims, ok := tok.Claims.(*Claims); ok && tok.Valid {
+	return validateClaims(tok)
+}
+
+func validateClaims(tok *jwt.Token) (*Claims, error) {
+	if claims, ok := tok.Claims.(*Claims); ok {
 		if claims.Version != uint64(CurrentVersion) {
 			return nil, ErrInvalidVersion
 		}
 		if claims.LicenseExpires == nil {
 			return nil, ErrMissingLicenseExpires
 		}
+		if claims.ExpiresAt == nil {
+			return nil, ErrMissingExp
+		}
 		return claims, nil
 	}
 	return nil, xerrors.New("unable to parse Claims")
 }
 
+// ParseClaimsIgnoreNbf validates a raw JWT, but ignores `nbf` claim. If otherwise valid, it returns
+// the claims.  If unparsable or invalid, it returns an error. Ignoring the `nbf` (not before) is
+// useful to determine if a JWT _will_ become valid at any point now or in the future.
+func ParseClaimsIgnoreNbf(rawJWT string, keys map[string]ed25519.PublicKey) (*Claims, error) {
+	tok, err := jwt.ParseWithClaims(
+		rawJWT,
+		&Claims{},
+		keyFunc(keys),
+		jwt.WithValidMethods(ValidMethods),
+	)
+	var vErr *jwt.ValidationError
+	if xerrors.As(err, &vErr) {
+		// zero out the NotValidYet error to check if there were other problems
+		vErr.Errors = vErr.Errors & (^jwt.ValidationErrorNotValidYet)
+		if vErr.Errors != 0 {
+			// There are other errors besides not being valid yet. We _could_ go
+			// through all the jwt.ValidationError bits and try to work out the
+			// correct error, but if we get here something very strange is
+			// going on so let's just return a generic error that says to get in
+			// touch with our support team.
+			return nil, ErrMultipleIssues
+		}
+	} else if err != nil {
+		return nil, err
+	}
+	return validateClaims(tok)
+}
+
 func keyFunc(keys map[string]ed25519.PublicKey) func(*jwt.Token) (interface{}, error) {
 	return func(j *jwt.Token) (interface{}, error) {
 		keyID, ok := j.Header[HeaderKeyID].(string)
diff --git a/enterprise/coderd/license/license_test.go b/enterprise/coderd/license/license_test.go
index db914170a34f2..8e5e3e0a567f3 100644
--- a/enterprise/coderd/license/license_test.go
+++ b/enterprise/coderd/license/license_test.go
@@ -826,6 +826,25 @@ func TestLicenseEntitlements(t *testing.T) {
 				assert.True(t, entitlements.Features[codersdk.FeatureCustomRoles].Enabled, "custom-roles enabled for premium")
 			},
 		},
+		{
+			Name: "CurrentAndFuture",
+			Licenses: []*coderdenttest.LicenseOptions{
+				enterpriseLicense().UserLimit(100),
+				premiumLicense().UserLimit(200).FutureTerm(time.Now()),
+			},
+			Enablements: defaultEnablements,
+			AssertEntitlements: func(t *testing.T, entitlements codersdk.Entitlements) {
+				assertEnterpriseFeatures(t, entitlements)
+				assertNoErrors(t, entitlements)
+				assertNoWarnings(t, entitlements)
+				userFeature := entitlements.Features[codersdk.FeatureUserLimit]
+				assert.Equalf(t, int64(100), *userFeature.Limit, "user limit")
+				assert.Equal(t, codersdk.EntitlementNotEntitled,
+					entitlements.Features[codersdk.FeatureMultipleOrganizations].Entitlement)
+				assert.Equal(t, codersdk.EntitlementNotEntitled,
+					entitlements.Features[codersdk.FeatureCustomRoles].Entitlement)
+			},
+		},
 	}
 
 	for _, tc := range testCases {
diff --git a/enterprise/coderd/licenses.go b/enterprise/coderd/licenses.go
index b3f38a8ca5f8d..8e713886555a5 100644
--- a/enterprise/coderd/licenses.go
+++ b/enterprise/coderd/licenses.go
@@ -86,25 +86,7 @@ func (api *API) postLicense(rw http.ResponseWriter, r *http.Request) {
 		return
 	}
 
-	rawClaims, err := license.ParseRaw(addLicense.License, api.LicenseKeys)
-	if err != nil {
-		httpapi.Write(ctx, rw, http.StatusBadRequest, codersdk.Response{
-			Message: "Invalid license",
-			Detail:  err.Error(),
-		})
-		return
-	}
-	exp, ok := rawClaims["exp"].(float64)
-	if !ok {
-		httpapi.Write(ctx, rw, http.StatusBadRequest, codersdk.Response{
-			Message: "Invalid license",
-			Detail:  "exp claim missing or not parsable",
-		})
-		return
-	}
-	expTime := time.Unix(int64(exp), 0)
-
-	claims, err := license.ParseClaims(addLicense.License, api.LicenseKeys)
+	claims, err := license.ParseClaimsIgnoreNbf(addLicense.License, api.LicenseKeys)
 	if err != nil {
 		httpapi.Write(ctx, rw, http.StatusBadRequest, codersdk.Response{
 			Message: "Invalid license",
@@ -134,7 +116,7 @@ func (api *API) postLicense(rw http.ResponseWriter, r *http.Request) {
 	dl, err := api.Database.InsertLicense(ctx, database.InsertLicenseParams{
 		UploadedAt: dbtime.Now(),
 		JWT:        addLicense.License,
-		Exp:        expTime,
+		Exp:        claims.ExpiresAt.Time,
 		UUID:       id,
 	})
 	if err != nil {
@@ -160,7 +142,15 @@ func (api *API) postLicense(rw http.ResponseWriter, r *http.Request) {
 		// don't fail the HTTP request, since we did write it successfully to the database
 	}
 
-	httpapi.Write(ctx, rw, http.StatusCreated, convertLicense(dl, rawClaims))
+	c, err := decodeClaims(dl)
+	if err != nil {
+		httpapi.Write(ctx, rw, http.StatusInternalServerError, codersdk.Response{
+			Message: "Failed to decode database response",
+			Detail:  err.Error(),
+		})
+		return
+	}
+	httpapi.Write(ctx, rw, http.StatusCreated, convertLicense(dl, c))
 }
 
 // postRefreshEntitlements forces an `updateEntitlements` call and publishes
diff --git a/enterprise/coderd/licenses_test.go b/enterprise/coderd/licenses_test.go
index c2f7d83fbbd6b..bbd6ef717fe8e 100644
--- a/enterprise/coderd/licenses_test.go
+++ b/enterprise/coderd/licenses_test.go
@@ -4,6 +4,7 @@ import (
 	"context"
 	"net/http"
 	"testing"
+	"time"
 
 	"github.com/google/uuid"
 	"github.com/stretchr/testify/assert"
@@ -82,6 +83,53 @@ func TestPostLicense(t *testing.T) {
 			t.Error("expected to get error status 400")
 		}
 	})
+
+	// Test a license that isn't yet valid, but will be in the future.  We should allow this so that
+	// operators can upload a license ahead of time.
+	t.Run("NotYet", func(t *testing.T) {
+		t.Parallel()
+		client, _ := coderdenttest.New(t, &coderdenttest.Options{DontAddLicense: true})
+		respLic := coderdenttest.AddLicense(t, client, coderdenttest.LicenseOptions{
+			AccountType: license.AccountTypeSalesforce,
+			AccountID:   "testing",
+			Features: license.Features{
+				codersdk.FeatureAuditLog: 1,
+			},
+			NotBefore: time.Now().Add(time.Hour),
+			GraceAt:   time.Now().Add(2 * time.Hour),
+			ExpiresAt: time.Now().Add(3 * time.Hour),
+		})
+		assert.GreaterOrEqual(t, respLic.ID, int32(0))
+		// just a couple spot checks for sanity
+		assert.Equal(t, "testing", respLic.Claims["account_id"])
+		features, err := respLic.FeaturesClaims()
+		require.NoError(t, err)
+		assert.EqualValues(t, 1, features[codersdk.FeatureAuditLog])
+	})
+
+	// Test we still reject a license that isn't valid yet, but has other issues (e.g. expired
+	// before it starts).
+	t.Run("NotEver", func(t *testing.T) {
+		t.Parallel()
+		client, _ := coderdenttest.New(t, &coderdenttest.Options{DontAddLicense: true})
+		lic := coderdenttest.GenerateLicense(t, coderdenttest.LicenseOptions{
+			AccountType: license.AccountTypeSalesforce,
+			AccountID:   "testing",
+			Features: license.Features{
+				codersdk.FeatureAuditLog: 1,
+			},
+			NotBefore: time.Now().Add(time.Hour),
+			GraceAt:   time.Now().Add(2 * time.Hour),
+			ExpiresAt: time.Now().Add(-time.Hour),
+		})
+		_, err := client.AddLicense(context.Background(), codersdk.AddLicenseRequest{
+			License: lic,
+		})
+		errResp := &codersdk.Error{}
+		require.ErrorAs(t, err, &errResp)
+		require.Equal(t, http.StatusBadRequest, errResp.StatusCode())
+		require.Contains(t, errResp.Detail, license.ErrMultipleIssues.Error())
+	})
 }
 
 func TestGetLicense(t *testing.T) {

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