diff --git a/api4/license.go b/api4/license.go
index ab63883502..fdd8e958f6 100644
--- a/api4/license.go
+++ b/api4/license.go
@@ -5,7 +5,9 @@ package api4
 
 import (
 	"bytes"
+	"encoding/json"
 	"io"
+	"io/ioutil"
 	"net/http"
 
 	"github.com/mattermost/mattermost-server/v5/audit"
@@ -13,6 +15,7 @@ import (
 )
 
 func (api *API) InitLicense() {
+	api.BaseRoutes.ApiRoot.Handle("/trial-license", api.ApiSessionRequired(requestTrialLicense)).Methods("POST")
 	api.BaseRoutes.ApiRoot.Handle("/license", api.ApiSessionRequired(addLicense)).Methods("POST")
 	api.BaseRoutes.ApiRoot.Handle("/license", api.ApiSessionRequired(removeLicense)).Methods("DELETE")
 	api.BaseRoutes.ApiRoot.Handle("/license/client", api.ApiHandler(getClientLicense)).Methods("GET")
@@ -138,3 +141,59 @@ func removeLicense(c *Context, w http.ResponseWriter, r *http.Request) {
 
 	ReturnStatusOK(w)
 }
+
+func requestTrialLicense(c *Context, w http.ResponseWriter, r *http.Request) {
+	auditRec := c.MakeAuditRecord("requestTrialLicense", audit.Fail)
+	defer c.LogAuditRec(auditRec)
+	c.LogAudit("attempt")
+
+	if !c.App.SessionHasPermissionTo(*c.App.Session(), model.PERMISSION_MANAGE_SYSTEM) {
+		c.SetPermissionError(model.PERMISSION_MANAGE_SYSTEM)
+		return
+	}
+
+	if *c.App.Config().ExperimentalSettings.RestrictSystemAdmin {
+		c.Err = model.NewAppError("removeLicense", "api.restricted_system_admin", nil, "", http.StatusForbidden)
+		return
+	}
+
+	var usersNumber struct {
+		Users int `json:"users"`
+	}
+
+	b, readErr := ioutil.ReadAll(r.Body)
+	if readErr != nil {
+		c.Err = model.NewAppError("removeLicense", "api.license.request-trial.bad-request", nil, "", http.StatusBadRequest)
+		return
+	}
+	json.Unmarshal(b, &usersNumber)
+	if usersNumber.Users == 0 {
+		c.Err = model.NewAppError("removeLicense", "api.license.request-trial.bad-request", nil, "", http.StatusBadRequest)
+		return
+	}
+
+	currentUser, err := c.App.GetUser(c.App.Session().UserId)
+	if err != nil {
+		c.Err = err
+		return
+	}
+
+	trialLicenseRequest := &model.TrialLicenseRequest{
+		ServerID: c.App.DiagnosticId(),
+		Name:     currentUser.GetDisplayName(model.SHOW_FULLNAME),
+		Email:    currentUser.Email,
+		SiteName: *c.App.Config().TeamSettings.SiteName,
+		SiteURL:  *c.App.Config().ServiceSettings.SiteURL,
+		Users:    usersNumber.Users,
+	}
+
+	if err := c.App.RequestTrialLicense(trialLicenseRequest); err != nil {
+		c.Err = err
+		return
+	}
+
+	auditRec.Success()
+	c.LogAudit("success")
+
+	ReturnStatusOK(w)
+}
diff --git a/app/app_iface.go b/app/app_iface.go
index 5a6e392603..dce0e3015b 100644
--- a/app/app_iface.go
+++ b/app/app_iface.go
@@ -253,6 +253,8 @@ type AppIface interface {
 	RenameChannel(channel *model.Channel, newChannelName string, newDisplayName string) (*model.Channel, *model.AppError)
 	// RenameTeam is used to rename the team Name and the DisplayName fields
 	RenameTeam(team *model.Team, newTeamName string, newDisplayName string) (*model.Team, *model.AppError)
+	// RequestTrialLicense request a trial license from the mattermost offical license server
+	RequestTrialLicense(trialRequest *model.TrialLicenseRequest) *model.AppError
 	// RevokeSessionsFromAllUsers will go through all the sessions active
 	// in the server and revoke them
 	RevokeSessionsFromAllUsers() *model.AppError
diff --git a/app/license.go b/app/license.go
index d09c2abd4d..a8441ceda2 100644
--- a/app/license.go
+++ b/app/license.go
@@ -4,6 +4,7 @@
 package app
 
 import (
+	"bytes"
 	"net/http"
 	"strings"
 
@@ -12,6 +13,8 @@ import (
 	"github.com/mattermost/mattermost-server/v5/utils"
 )
 
+const requestTrialURL = "https://customers.mattermost.com/api/v1/trials"
+
 func (a *App) LoadLicense() {
 	licenseId := ""
 	props, err := a.Srv().Store.System().Get()
@@ -214,3 +217,22 @@ func (a *App) GetSanitizedClientLicense() map[string]string {
 
 	return sanitizedLicense
 }
+
+// RequestTrialLicense request a trial license from the mattermost offical license server
+func (a *App) RequestTrialLicense(trialRequest *model.TrialLicenseRequest) *model.AppError {
+	resp, err := http.Post(requestTrialURL, "application/json", bytes.NewBuffer([]byte(trialRequest.ToJson())))
+	if err != nil {
+		return model.NewAppError("RequestTrialLicense", "api.license.request_trial_license.app_error", nil, err.Error(), http.StatusBadRequest)
+	}
+	defer resp.Body.Close()
+	licenseResponse := model.MapFromJson(resp.Body)
+
+	if _, err := a.SaveLicense([]byte(licenseResponse["license"])); err != nil {
+		return err
+	}
+
+	a.ReloadConfig()
+	a.InvalidateAllCaches()
+
+	return nil
+}
diff --git a/app/opentracing_layer.go b/app/opentracing_layer.go
index 940b60d5b9..c71d68b6d8 100644
--- a/app/opentracing_layer.go
+++ b/app/opentracing_layer.go
@@ -11395,6 +11395,28 @@ func (a *OpenTracingAppLayer) RenameTeam(team *model.Team, newTeamName string, n
 	return resultVar0, resultVar1
 }
 
+func (a *OpenTracingAppLayer) RequestTrialLicense(trialRequest *model.TrialLicenseRequest) *model.AppError {
+	origCtx := a.ctx
+	span, newCtx := tracing.StartSpanWithParentByContext(a.ctx, "app.RequestTrialLicense")
+
+	a.ctx = newCtx
+	a.app.Srv().Store.SetContext(newCtx)
+	defer func() {
+		a.app.Srv().Store.SetContext(origCtx)
+		a.ctx = origCtx
+	}()
+
+	defer span.Finish()
+	resultVar0 := a.app.RequestTrialLicense(trialRequest)
+
+	if resultVar0 != nil {
+		span.LogFields(spanlog.Error(resultVar0))
+		ext.Error.Set(span, true)
+	}
+
+	return resultVar0
+}
+
 func (a *OpenTracingAppLayer) ResetPasswordFromToken(userSuppliedTokenString string, newPassword string) *model.AppError {
 	origCtx := a.ctx
 	span, newCtx := tracing.StartSpanWithParentByContext(a.ctx, "app.ResetPasswordFromToken")
diff --git a/i18n/en.json b/i18n/en.json
index 9b48530670..dc604868f8 100644
--- a/i18n/en.json
+++ b/i18n/en.json
@@ -1488,6 +1488,14 @@
     "id": "api.license.remove_expired_license.failed.error",
     "translation": "Failed to send the disable license email successfully."
   },
+  {
+    "id": "api.license.request-trial.bad-request",
+    "translation": "The number of users requested is not correct."
+  },
+  {
+    "id": "api.license.request_trial_license.app_error",
+    "translation": "Unable to get a trial license, please try again or contact with support@mattermost.com."
+  },
   {
     "id": "api.marshal_error",
     "translation": "marshal error"
diff --git a/model/client4.go b/model/client4.go
index 3eacb46176..8a8d55fd9b 100644
--- a/model/client4.go
+++ b/model/client4.go
@@ -5102,3 +5102,14 @@ func (c *Client4) GetChannelMemberCountsByGroup(channelID string, includeTimezon
 	defer closeBody(r)
 	return ChannelMemberCountsByGroupFromJson(r.Body), BuildResponse(r)
 }
+
+// RequestTrialLicense will request a trial license and install it in the server
+func (c *Client4) RequestTrialLicense(users int) (bool, *Response) {
+	b, _ := json.Marshal(map[string]int{"users": users})
+	r, err := c.DoApiPost("/trial-license", string(b))
+	if err != nil {
+		return false, BuildErrorResponse(r, err)
+	}
+	defer closeBody(r)
+	return CheckStatusOK(r), BuildResponse(r)
+}
diff --git a/model/license.go b/model/license.go
index 80e7961494..c0c401e240 100644
--- a/model/license.go
+++ b/model/license.go
@@ -40,6 +40,20 @@ type Customer struct {
 	Company string `json:"company"`
 }
 
+type TrialLicenseRequest struct {
+	ServerID string `json:"server_id"`
+	Email    string `json:"email"`
+	Name     string `json:"name"`
+	SiteURL  string `json:"site_url"`
+	SiteName string `json:"site_name"`
+	Users    int    `json:"users"`
+}
+
+func (tlr *TrialLicenseRequest) ToJson() string {
+	b, _ := json.Marshal(tlr)
+	return string(b)
+}
+
 type Features struct {
 	Users                     *int  `json:"users"`
 	LDAP                      *bool `json:"ldap"`