diff --git a/.github/workflows/pr-deploy.yaml b/.github/workflows/pr-deploy.yaml
index e86ad1f3dd351..6ca35c82eebeb 100644
--- a/.github/workflows/pr-deploy.yaml
+++ b/.github/workflows/pr-deploy.yaml
@@ -425,7 +425,7 @@ jobs:
             --first-user-username coder \
             --first-user-email pr${{ env.PR_NUMBER }}@coder.com \
             --first-user-password $password \
-            --first-user-trial \
+            --first-user-trial=false \
             --use-token-as-session \
             https://${{ env.PR_HOSTNAME }}
 
diff --git a/cli/login.go b/cli/login.go
index 484de69fdf1b5..3bb4f0796e4a5 100644
--- a/cli/login.go
+++ b/cli/login.go
@@ -267,12 +267,59 @@ func (r *RootCmd) login() *serpent.Command {
 					trial = v == "yes" || v == "y"
 				}
 
+				var trialInfo codersdk.CreateFirstUserTrialInfo
+				if trial {
+					if trialInfo.FirstName == "" {
+						trialInfo.FirstName, err = promptTrialInfo(inv, "firstName")
+						if err != nil {
+							return err
+						}
+					}
+					if trialInfo.LastName == "" {
+						trialInfo.LastName, err = promptTrialInfo(inv, "lastName")
+						if err != nil {
+							return err
+						}
+					}
+					if trialInfo.PhoneNumber == "" {
+						trialInfo.PhoneNumber, err = promptTrialInfo(inv, "phoneNumber")
+						if err != nil {
+							return err
+						}
+					}
+					if trialInfo.JobTitle == "" {
+						trialInfo.JobTitle, err = promptTrialInfo(inv, "jobTitle")
+						if err != nil {
+							return err
+						}
+					}
+					if trialInfo.CompanyName == "" {
+						trialInfo.CompanyName, err = promptTrialInfo(inv, "companyName")
+						if err != nil {
+							return err
+						}
+					}
+					if trialInfo.Country == "" {
+						trialInfo.Country, err = promptCountry(inv)
+						if err != nil {
+							return err
+						}
+					}
+					if trialInfo.Developers == "" {
+						trialInfo.Developers, err = promptDevelopers(inv)
+						if err != nil {
+							return err
+						}
+					}
+				}
+
 				_, err = client.CreateFirstUser(ctx, codersdk.CreateFirstUserRequest{
-					Email:    email,
-					Username: username,
-					Name:     name,
-					Password: password,
-					Trial:    trial,
+					Email:     email,
+					Username:  username,
+					Name:      name,
+					Password:  password,
+					Trial:     trial,
+					TrialInfo: trialInfo,
 				})
 				if err != nil {
 					return xerrors.Errorf("create initial user: %w", err)
@@ -449,3 +496,75 @@ func openURL(inv *serpent.Invocation, urlToOpen string) error {
 
 	return browser.OpenURL(urlToOpen)
 }
+
+func promptTrialInfo(inv *serpent.Invocation, fieldName string) (string, error) {
+	value, err := cliui.Prompt(inv, cliui.PromptOptions{
+		Text: fmt.Sprintf("Please enter %s:", pretty.Sprint(cliui.DefaultStyles.Field, fieldName)),
+		Validate: func(s string) error {
+			if strings.TrimSpace(s) == "" {
+				return xerrors.Errorf("%s is required", fieldName)
+			}
+			return nil
+		},
+	})
+	if err != nil {
+		if errors.Is(err, cliui.Canceled) {
+			return "", nil
+		}
+		return "", err
+	}
+	return value, nil
+}
+
+func promptDevelopers(inv *serpent.Invocation) (string, error) {
+	options := []string{"1-100", "101-500", "501-1000", "1001-2500", "2500+"}
+	selection, err := cliui.Select(inv, cliui.SelectOptions{
+		Options:    options,
+		HideSearch: false,
+		Message:    "Select the number of developers:",
+	})
+	if err != nil {
+		return "", xerrors.Errorf("select developers: %w", err)
+	}
+	return selection, nil
+}
+
+func promptCountry(inv *serpent.Invocation) (string, error) {
+	countries := []string{
+		"Afghanistan", "Åland Islands", "Albania", "Algeria", "American Samoa", "Andorra", "Angola", "Anguilla", "Antarctica", "Antigua and Barbuda",
+		"Argentina", "Armenia", "Aruba", "Australia", "Austria", "Azerbaijan", "Bahamas", "Bahrain", "Bangladesh", "Barbados",
+		"Belarus", "Belgium", "Belize", "Benin", "Bermuda", "Bhutan", "Bolivia, Plurinational State of", "Bonaire, Sint Eustatius and Saba", "Bosnia and Herzegovina", "Botswana",
+		"Bouvet Island", "Brazil", "British Indian Ocean Territory", "Brunei Darussalam", "Bulgaria", "Burkina Faso", "Burundi", "Cambodia", "Cameroon", "Canada",
+		"Cape Verde", "Cayman Islands", "Central African Republic", "Chad", "Chile", "China", "Christmas Island", "Cocos (Keeling) Islands", "Colombia", "Comoros",
+		"Congo", "Congo, the Democratic Republic of the", "Cook Islands", "Costa Rica", "Côte d'Ivoire", "Croatia", "Cuba", "Curaçao", "Cyprus", "Czech Republic",
+		"Denmark", "Djibouti", "Dominica", "Dominican Republic", "Ecuador", "Egypt", "El Salvador", "Equatorial Guinea", "Eritrea", "Estonia",
+		"Ethiopia", "Falkland Islands (Malvinas)", "Faroe Islands", "Fiji", "Finland", "France", "French Guiana", "French Polynesia", "French Southern Territories", "Gabon",
+		"Gambia", "Georgia", "Germany", "Ghana", "Gibraltar", "Greece", "Greenland", "Grenada", "Guadeloupe", "Guam",
+		"Guatemala", "Guernsey", "Guinea", "Guinea-Bissau", "Guyana", "Haiti", "Heard Island and McDonald Islands", "Holy See (Vatican City State)", "Honduras", "Hong Kong",
+		"Hungary", "Iceland", "India", "Indonesia", "Iran, Islamic Republic of", "Iraq", "Ireland", "Isle of Man", "Israel", "Italy",
+		"Jamaica", "Japan", "Jersey", "Jordan", "Kazakhstan", "Kenya", "Kiribati", "Korea, Democratic People's Republic of", "Korea, Republic of", "Kuwait",
+		"Kyrgyzstan", "Lao People's Democratic Republic", "Latvia", "Lebanon", "Lesotho", "Liberia", "Libya", "Liechtenstein", "Lithuania", "Luxembourg",
+		"Macao", "Macedonia, the Former Yugoslav Republic of", "Madagascar", "Malawi", "Malaysia", "Maldives", "Mali", "Malta", "Marshall Islands", "Martinique",
+		"Mauritania", "Mauritius", "Mayotte", "Mexico", "Micronesia, Federated States of", "Moldova, Republic of", "Monaco", "Mongolia", "Montenegro", "Montserrat",
+		"Morocco", "Mozambique", "Myanmar", "Namibia", "Nauru", "Nepal", "Netherlands", "New Caledonia", "New Zealand", "Nicaragua",
+		"Niger", "Nigeria", "Niue", "Norfolk Island", "Northern Mariana Islands", "Norway", "Oman", "Pakistan", "Palau", "Palestine, State of",
+		"Panama", "Papua New Guinea", "Paraguay", "Peru", "Philippines", "Pitcairn", "Poland", "Portugal", "Puerto Rico", "Qatar",
+		"Réunion", "Romania", "Russian Federation", "Rwanda", "Saint Barthélemy", "Saint Helena, Ascension and Tristan da Cunha", "Saint Kitts and Nevis", "Saint Lucia", "Saint Martin (French part)", "Saint Pierre and Miquelon",
+		"Saint Vincent and the Grenadines", "Samoa", "San Marino", "Sao Tome and Principe", "Saudi Arabia", "Senegal", "Serbia", "Seychelles", "Sierra Leone", "Singapore",
+		"Sint Maarten (Dutch part)", "Slovakia", "Slovenia", "Solomon Islands", "Somalia", "South Africa", "South Georgia and the South Sandwich Islands", "South Sudan", "Spain", "Sri Lanka",
+		"Sudan", "Suriname", "Svalbard and Jan Mayen", "Swaziland", "Sweden", "Switzerland", "Syrian Arab Republic", "Taiwan, Province of China", "Tajikistan", "Tanzania, United Republic of",
+		"Thailand", "Timor-Leste", "Togo", "Tokelau", "Tonga", "Trinidad and Tobago", "Tunisia", "Turkey", "Turkmenistan", "Turks and Caicos Islands",
+		"Tuvalu", "Uganda", "Ukraine", "United Arab Emirates", "United Kingdom", "United States", "United States Minor Outlying Islands", "Uruguay", "Uzbekistan", "Vanuatu",
+		"Venezuela, Bolivarian Republic of", "Vietnam", "Virgin Islands, British", "Virgin Islands, U.S.", "Wallis and Futuna", "Western Sahara", "Yemen", "Zambia", "Zimbabwe",
+	}
+
+	selection, err := cliui.Select(inv, cliui.SelectOptions{
+		Options:    countries,
+		Message:    "Select the country:",
+		HideSearch: false,
+	})
+	if err != nil {
+		return "", xerrors.Errorf("select country: %w", err)
+	}
+	return selection, nil
+}
diff --git a/cli/login_test.go b/cli/login_test.go
index 0428c332d02b0..9a86e7caad351 100644
--- a/cli/login_test.go
+++ b/cli/login_test.go
@@ -96,6 +96,58 @@ func TestLogin(t *testing.T) {
 			"password", coderdtest.FirstUserParams.Password,
 			"password", coderdtest.FirstUserParams.Password, // confirm
 			"trial", "yes",
+			"firstName", coderdtest.TrialUserParams.FirstName,
+			"lastName", coderdtest.TrialUserParams.LastName,
+			"phoneNumber", coderdtest.TrialUserParams.PhoneNumber,
+			"jobTitle", coderdtest.TrialUserParams.JobTitle,
+			"companyName", coderdtest.TrialUserParams.CompanyName,
+			// `developers` and `country` `cliui.Select` automatically selects the first option during tests.
+		}
+		for i := 0; i < len(matches); i += 2 {
+			match := matches[i]
+			value := matches[i+1]
+			pty.ExpectMatch(match)
+			pty.WriteLine(value)
+		}
+		pty.ExpectMatch("Welcome to Coder")
+		<-doneChan
+		ctx := testutil.Context(t, testutil.WaitShort)
+		resp, err := client.LoginWithPassword(ctx, codersdk.LoginWithPasswordRequest{
+			Email:    coderdtest.FirstUserParams.Email,
+			Password: coderdtest.FirstUserParams.Password,
+		})
+		require.NoError(t, err)
+		client.SetSessionToken(resp.SessionToken)
+		me, err := client.User(ctx, codersdk.Me)
+		require.NoError(t, err)
+		assert.Equal(t, coderdtest.FirstUserParams.Username, me.Username)
+		assert.Equal(t, coderdtest.FirstUserParams.Name, me.Name)
+		assert.Equal(t, coderdtest.FirstUserParams.Email, me.Email)
+	})
+
+	t.Run("InitialUserTTYWithNoTrial", func(t *testing.T) {
+		t.Parallel()
+		client := coderdtest.New(t, nil)
+		// The --force-tty flag is required on Windows, because the `isatty` library does not
+		// accurately detect Windows ptys when they are not attached to a process:
+		// https://github.com/mattn/go-isatty/issues/59
+		doneChan := make(chan struct{})
+		root, _ := clitest.New(t, "login", "--force-tty", client.URL.String())
+		pty := ptytest.New(t).Attach(root)
+		go func() {
+			defer close(doneChan)
+			err := root.Run()
+			assert.NoError(t, err)
+		}()
+
+		matches := []string{
+			"first user?", "yes",
+			"username", coderdtest.FirstUserParams.Username,
+			"name", coderdtest.FirstUserParams.Name,
+			"email", coderdtest.FirstUserParams.Email,
+			"password", coderdtest.FirstUserParams.Password,
+			"password", coderdtest.FirstUserParams.Password, // confirm
+			"trial", "no",
 		}
 		for i := 0; i < len(matches); i += 2 {
 			match := matches[i]
@@ -142,6 +194,12 @@ func TestLogin(t *testing.T) {
 			"password", coderdtest.FirstUserParams.Password,
 			"password", coderdtest.FirstUserParams.Password, // confirm
 			"trial", "yes",
+			"firstName", coderdtest.TrialUserParams.FirstName,
+			"lastName", coderdtest.TrialUserParams.LastName,
+			"phoneNumber", coderdtest.TrialUserParams.PhoneNumber,
+			"jobTitle", coderdtest.TrialUserParams.JobTitle,
+			"companyName", coderdtest.TrialUserParams.CompanyName,
+			// `developers` and `country` `cliui.Select` automatically selects the first option during tests.
 		}
 		for i := 0; i < len(matches); i += 2 {
 			match := matches[i]
@@ -185,6 +243,12 @@ func TestLogin(t *testing.T) {
 			"password", coderdtest.FirstUserParams.Password,
 			"password", coderdtest.FirstUserParams.Password, // confirm
 			"trial", "yes",
+			"firstName", coderdtest.TrialUserParams.FirstName,
+			"lastName", coderdtest.TrialUserParams.LastName,
+			"phoneNumber", coderdtest.TrialUserParams.PhoneNumber,
+			"jobTitle", coderdtest.TrialUserParams.JobTitle,
+			"companyName", coderdtest.TrialUserParams.CompanyName,
+			// `developers` and `country` `cliui.Select` automatically selects the first option during tests.
 		}
 		for i := 0; i < len(matches); i += 2 {
 			match := matches[i]
@@ -220,6 +284,17 @@ func TestLogin(t *testing.T) {
 		)
 		pty := ptytest.New(t).Attach(inv)
 		w := clitest.StartWithWaiter(t, inv)
+		pty.ExpectMatch("firstName")
+		pty.WriteLine(coderdtest.TrialUserParams.FirstName)
+		pty.ExpectMatch("lastName")
+		pty.WriteLine(coderdtest.TrialUserParams.LastName)
+		pty.ExpectMatch("phoneNumber")
+		pty.WriteLine(coderdtest.TrialUserParams.PhoneNumber)
+		pty.ExpectMatch("jobTitle")
+		pty.WriteLine(coderdtest.TrialUserParams.JobTitle)
+		pty.ExpectMatch("companyName")
+		pty.WriteLine(coderdtest.TrialUserParams.CompanyName)
+		// `developers` and `country` `cliui.Select` automatically selects the first option during tests.
 		pty.ExpectMatch("Welcome to Coder")
 		w.RequireSuccess()
 		ctx := testutil.Context(t, testutil.WaitShort)
@@ -248,6 +323,17 @@ func TestLogin(t *testing.T) {
 		)
 		pty := ptytest.New(t).Attach(inv)
 		w := clitest.StartWithWaiter(t, inv)
+		pty.ExpectMatch("firstName")
+		pty.WriteLine(coderdtest.TrialUserParams.FirstName)
+		pty.ExpectMatch("lastName")
+		pty.WriteLine(coderdtest.TrialUserParams.LastName)
+		pty.ExpectMatch("phoneNumber")
+		pty.WriteLine(coderdtest.TrialUserParams.PhoneNumber)
+		pty.ExpectMatch("jobTitle")
+		pty.WriteLine(coderdtest.TrialUserParams.JobTitle)
+		pty.ExpectMatch("companyName")
+		pty.WriteLine(coderdtest.TrialUserParams.CompanyName)
+		// `developers` and `country` `cliui.Select` automatically selects the first option during tests.
 		pty.ExpectMatch("Welcome to Coder")
 		w.RequireSuccess()
 		ctx := testutil.Context(t, testutil.WaitShort)
@@ -299,12 +385,21 @@ func TestLogin(t *testing.T) {
 		// Validate that we reprompt for matching passwords.
 		pty.ExpectMatch("Passwords do not match")
 		pty.ExpectMatch("Enter a " + pretty.Sprint(cliui.DefaultStyles.Field, "password"))
-
 		pty.WriteLine(coderdtest.FirstUserParams.Password)
 		pty.ExpectMatch("Confirm")
 		pty.WriteLine(coderdtest.FirstUserParams.Password)
 		pty.ExpectMatch("trial")
 		pty.WriteLine("yes")
+		pty.ExpectMatch("firstName")
+		pty.WriteLine(coderdtest.TrialUserParams.FirstName)
+		pty.ExpectMatch("lastName")
+		pty.WriteLine(coderdtest.TrialUserParams.LastName)
+		pty.ExpectMatch("phoneNumber")
+		pty.WriteLine(coderdtest.TrialUserParams.PhoneNumber)
+		pty.ExpectMatch("jobTitle")
+		pty.WriteLine(coderdtest.TrialUserParams.JobTitle)
+		pty.ExpectMatch("companyName")
+		pty.WriteLine(coderdtest.TrialUserParams.CompanyName)
 		pty.ExpectMatch("Welcome to Coder")
 		<-doneChan
 	})
diff --git a/coderd/coderdtest/coderdtest.go b/coderd/coderdtest/coderdtest.go
index 05c31f35bd20a..5ed667aded5e8 100644
--- a/coderd/coderdtest/coderdtest.go
+++ b/coderd/coderdtest/coderdtest.go
@@ -651,6 +651,16 @@ var FirstUserParams = codersdk.CreateFirstUserRequest{
 	Name:     "Test User",
 }
 
+var TrialUserParams = codersdk.CreateFirstUserTrialInfo{
+	FirstName:   "John",
+	LastName:    "Doe",
+	PhoneNumber: "9999999999",
+	JobTitle:    "Engineer",
+	CompanyName: "Acme Inc",
+	Country:     "United States",
+	Developers:  "10-50",
+}
+
 // CreateFirstUser creates a user with preset credentials and authenticates
 // with the passed in codersdk client.
 func CreateFirstUser(t testing.TB, client *codersdk.Client) codersdk.CreateFirstUserResponse {
diff --git a/scripts/develop.sh b/scripts/develop.sh
index bdaf81c7536e5..7dfad72d2e9f6 100755
--- a/scripts/develop.sh
+++ b/scripts/develop.sh
@@ -164,7 +164,7 @@ fatal() {
 
 	if [ ! -f "${PROJECT_ROOT}/.coderv2/developsh-did-first-setup" ]; then
 		# Try to create the initial admin user.
-		if "${CODER_DEV_SHIM}" login http://127.0.0.1:3000 --first-user-username=admin --first-user-email=admin@coder.com --first-user-password="${password}" --first-user-full-name="Admin User" --first-user-trial=true; then
+		if "${CODER_DEV_SHIM}" login http://127.0.0.1:3000 --first-user-username=admin --first-user-email=admin@coder.com --first-user-password="${password}" --first-user-full-name="Admin User" --first-user-trial=false; then
 			# Only create this file if an admin user was successfully
 			# created, otherwise we won't retry on a later attempt.
 			touch "${PROJECT_ROOT}/.coderv2/developsh-did-first-setup"
diff --git a/site/src/pages/SetupPage/countries.tsx b/site/src/pages/SetupPage/countries.tsx
index 0fcebc25ac54d..9b13b6b6be0d9 100644
--- a/site/src/pages/SetupPage/countries.tsx
+++ b/site/src/pages/SetupPage/countries.tsx
@@ -964,7 +964,7 @@ export const countries = [
 		flag: "🇻🇪",
 	},
 	{
-		name: "Viet Nam",
+		name: "Vietnam",
 		flag: "🇻🇳",
 	},
 	{