diff --git a/cli/cliui/prompt.go b/cli/cliui/prompt.go
index 89e10f42232db..607274188aa5f 100644
--- a/cli/cliui/prompt.go
+++ b/cli/cliui/prompt.go
@@ -2,7 +2,9 @@ package cliui
 
 import (
 	"bufio"
+	"encoding/json"
 	"fmt"
+	"io"
 	"os"
 	"os/signal"
 	"strings"
@@ -45,12 +47,22 @@ func Prompt(cmd *cobra.Command, opts PromptOptions) (string, error) {
 		} else {
 			reader := bufio.NewReader(cmd.InOrStdin())
 			line, err = reader.ReadString('\n')
-			// Multiline with single quotes!
-			if err == nil && strings.HasPrefix(line, "'") {
-				rest, err := reader.ReadString('\'')
+
+			// Check if the first line beings with JSON object or array chars.
+			// This enables multiline JSON to be pasted into an input, and have
+			// it parse properly.
+			if err == nil && (strings.HasPrefix(line, "{") || strings.HasPrefix(line, "[")) {
+				pipeReader, pipeWriter := io.Pipe()
+				defer pipeWriter.Close()
+				defer pipeReader.Close()
+				go func() {
+					_, _ = pipeWriter.Write([]byte(line))
+					_, _ = reader.WriteTo(pipeWriter)
+				}()
+				var rawMessage json.RawMessage
+				err := json.NewDecoder(pipeReader).Decode(&rawMessage)
 				if err == nil {
-					line += rest
-					line = strings.Trim(line, "'")
+					line = string(rawMessage)
 				}
 			}
 		}
diff --git a/cli/cliui/prompt_test.go b/cli/cliui/prompt_test.go
index ee43c70bc7740..c01c2d2e78dc5 100644
--- a/cli/cliui/prompt_test.go
+++ b/cli/cliui/prompt_test.go
@@ -2,7 +2,6 @@ package cliui_test
 
 import (
 	"context"
-	"runtime"
 	"testing"
 
 	"github.com/spf13/cobra"
@@ -47,7 +46,7 @@ func TestPrompt(t *testing.T) {
 		require.Equal(t, "yes", <-doneChan)
 	})
 
-	t.Run("Multiline", func(t *testing.T) {
+	t.Run("JSON", func(t *testing.T) {
 		t.Parallel()
 		ptty := ptytest.New(t)
 		doneChan := make(chan string)
@@ -59,13 +58,44 @@ func TestPrompt(t *testing.T) {
 			doneChan <- resp
 		}()
 		ptty.ExpectMatch("Example")
-		ptty.WriteLine("'this is a")
-		ptty.WriteLine("test'")
-		newline := "\n"
-		if runtime.GOOS == "windows" {
-			newline = "\r\n"
-		}
-		require.Equal(t, "this is a"+newline+"test", <-doneChan)
+		ptty.WriteLine("{}")
+		require.Equal(t, "{}", <-doneChan)
+	})
+
+	t.Run("BadJSON", func(t *testing.T) {
+		t.Parallel()
+		ptty := ptytest.New(t)
+		doneChan := make(chan string)
+		go func() {
+			resp, err := newPrompt(ptty, cliui.PromptOptions{
+				Text: "Example",
+			})
+			require.NoError(t, err)
+			doneChan <- resp
+		}()
+		ptty.ExpectMatch("Example")
+		ptty.WriteLine("{a")
+		require.Equal(t, "{a", <-doneChan)
+	})
+
+	t.Run("MultilineJSON", func(t *testing.T) {
+		t.Parallel()
+		ptty := ptytest.New(t)
+		doneChan := make(chan string)
+		go func() {
+			resp, err := newPrompt(ptty, cliui.PromptOptions{
+				Text: "Example",
+			})
+			require.NoError(t, err)
+			doneChan <- resp
+		}()
+		ptty.ExpectMatch("Example")
+		ptty.WriteLine(`{
+"test": "wow"
+}`)
+		require.Equal(t, `{
+"test": "wow"
+}`, <-doneChan)
 	})
 }
 
diff --git a/cli/workspacecreate_test.go b/cli/workspacecreate_test.go
index 5dd85e0833c93..d076de8d8d6c6 100644
--- a/cli/workspacecreate_test.go
+++ b/cli/workspacecreate_test.go
@@ -3,10 +3,11 @@ package cli_test
 import (
 	"testing"
 
+	"github.com/stretchr/testify/require"
+
 	"github.com/coder/coder/cli/clitest"
 	"github.com/coder/coder/coderd/coderdtest"
 	"github.com/coder/coder/pty/ptytest"
-	"github.com/stretchr/testify/require"
 )
 
 func TestWorkspaceCreate(t *testing.T) {
diff --git a/database/postgres/postgres.go b/database/postgres/postgres.go
index 563fd4c63b2b1..89fcf0000ddea 100644
--- a/database/postgres/postgres.go
+++ b/database/postgres/postgres.go
@@ -9,10 +9,11 @@ import (
 	"sync"
 	"time"
 
-	"github.com/coder/coder/cryptorand"
 	"github.com/ory/dockertest/v3"
 	"github.com/ory/dockertest/v3/docker"
 	"golang.org/x/xerrors"
+
+	"github.com/coder/coder/cryptorand"
 )
 
 // Required to prevent port collision during container creation.