diff --git a/internal/command/views/cloud_test.go b/internal/command/views/cloud_test.go
index 358a895bdd..63167fffdd 100644
--- a/internal/command/views/cloud_test.go
+++ b/internal/command/views/cloud_test.go
@@ -2,11 +2,11 @@ package views
 
 import (
 	"fmt"
+	"net/http"
 	"strings"
 	"testing"
 	"time"
 
-	"github.com/google/go-cmp/cmp"
 	"github.com/hashicorp/hcl/v2"
 	"github.com/hashicorp/terraform/internal/command/arguments"
 	"github.com/hashicorp/terraform/internal/terminal"
@@ -14,6 +14,71 @@ import (
 	tfversion "github.com/hashicorp/terraform/version"
 )
 
+func TestNewCloudHuman_RetryLog(t *testing.T) {
+	t.Run("first retry, no output", func(t *testing.T) {
+		streams, done := terminal.StreamsForTesting(t)
+		newCloud := NewCloud(arguments.ViewHuman, NewView(streams).SetRunningInAutomation(true))
+		cloudHuman, ok := newCloud.(*CloudHuman)
+		if !ok {
+			t.Fatalf("unexpected return type %T", newCloud)
+		}
+
+		cloudHuman.RetryLog(0, nil)
+		output := done(t).All()
+		if output != "" {
+			t.Fatalf("expected no output for the first retry attempt, but got: %s", output)
+		}
+	})
+
+	t.Run("second retry, server error", func(t *testing.T) {
+		streams, done := terminal.StreamsForTesting(t)
+		newCloud := NewCloud(arguments.ViewHuman, NewView(streams).SetRunningInAutomation(true))
+		cloudHuman, ok := newCloud.(*CloudHuman)
+		if !ok {
+			t.Fatalf("unexpected return type %T", newCloud)
+		}
+
+		cloudHuman.RetryLog(1, &http.Response{StatusCode: 500})
+		output := done(t).All()
+		expected := "There was an error connecting to HCP Terraform. Please do not exit\nTerraform to prevent data loss! Trying to restore the connection..."
+		if !strings.Contains(output, expected) {
+			t.Fatalf("expected output to contain: %s, but got %s", expected, output)
+		}
+	})
+
+	t.Run("subsequent retry with elapsed time", func(t *testing.T) {
+		streams, done := terminal.StreamsForTesting(t)
+		newCloud := NewCloud(arguments.ViewHuman, NewView(streams).SetRunningInAutomation(true))
+		cloudHuman, ok := newCloud.(*CloudHuman)
+		if !ok {
+			t.Fatalf("unexpected return type %T", newCloud)
+		}
+
+		cloudHuman.lastRetry = time.Now().Add(-2 * time.Second) // Simulate a delay of 2 seconds
+		cloudHuman.RetryLog(2, &http.Response{StatusCode: 500})
+		output := done(t).All()
+		expected := "Still trying to restore the connection... (2s elapsed)"
+		if !strings.Contains(output, expected) {
+			t.Fatalf("expected output to contain: %s, but got %s", expected, output)
+		}
+	})
+
+	t.Run("retry with 429 status, no output", func(t *testing.T) {
+		streams, done := terminal.StreamsForTesting(t)
+		newCloud := NewCloud(arguments.ViewHuman, NewView(streams).SetRunningInAutomation(true))
+		cloudHuman, ok := newCloud.(*CloudHuman)
+		if !ok {
+			t.Fatalf("unexpected return type %T", newCloud)
+		}
+
+		cloudHuman.RetryLog(2, &http.Response{StatusCode: 429})
+		output := done(t).All()
+		if output != "" {
+			t.Fatalf("expected no output for status code 429, but got: %s", output)
+		}
+	})
+}
+
 func TestNewCloud_unsupportedViewDiagnostics(t *testing.T) {
 	defer func() {
 		r := recover()
@@ -67,24 +132,6 @@ func TestNewCloud_humanViewOutput(t *testing.T) {
 	})
 }
 
-func TestNewCloud_humanViewPrepareMessage(t *testing.T) {
-	t.Run("existing message code", func(t *testing.T) {
-		streams, _ := terminal.StreamsForTesting(t)
-
-		newCloud := NewCloud(arguments.ViewHuman, NewView(streams).SetRunningInAutomation(true))
-		if _, ok := newCloud.(*CloudHuman); !ok {
-			t.Fatalf("unexpected return type %t", newCloud)
-		}
-
-		want := "\nThere was an error connecting to HCP Terraform. Please do not exit\nTerraform to prevent data loss! Trying to restore the connection..."
-
-		actual := newCloud.PrepareMessage(InitialRetryErrorMessage)
-		if !cmp.Equal(want, actual) {
-			t.Errorf("unexpected output: %s", cmp.Diff(want, actual))
-		}
-	})
-}
-
 func TestNewCloud_humanViewDiagnostics(t *testing.T) {
 	streams, done := terminal.StreamsForTesting(t)
 
@@ -103,6 +150,126 @@ func TestNewCloud_humanViewDiagnostics(t *testing.T) {
 	}
 }
 
+func TestNewCloudJSON_RetryLog(t *testing.T) {
+	t.Run("attempt 0, no output", func(t *testing.T) {
+		streams, done := terminal.StreamsForTesting(t)
+		newCloud := NewCloud(arguments.ViewJSON, NewView(streams).SetRunningInAutomation(true))
+		cloudJSON, ok := newCloud.(*CloudJSON)
+		if !ok {
+			t.Fatalf("unexpected return type %T", newCloud)
+		}
+
+		cloudJSON.RetryLog(0, nil)
+
+		version := tfversion.String()
+		want := []map[string]interface{}{
+			{
+				"@level":    "info",
+				"@message":  fmt.Sprintf("Terraform %s", version),
+				"@module":   "terraform.ui",
+				"terraform": version,
+				"type":      "version",
+				"ui":        JSON_UI_VERSION,
+			},
+		}
+		actual := done(t).Stdout()
+		testJSONViewOutputEqualsFull(t, actual, want)
+	})
+
+	t.Run("attempt 1, server error", func(t *testing.T) {
+		streams, done := terminal.StreamsForTesting(t)
+		newCloud := NewCloud(arguments.ViewJSON, NewView(streams).SetRunningInAutomation(true))
+		cloudJSON, ok := newCloud.(*CloudJSON)
+		if !ok {
+			t.Fatalf("unexpected return type %T", newCloud)
+		}
+
+		cloudJSON.RetryLog(1, &http.Response{StatusCode: 500})
+
+		version := tfversion.String()
+		want := []map[string]interface{}{
+			{
+				"@level":    "info",
+				"@message":  fmt.Sprintf("Terraform %s", version),
+				"@module":   "terraform.ui",
+				"terraform": version,
+				"type":      "version",
+				"ui":        JSON_UI_VERSION,
+			},
+			{
+				"@level":       "info",
+				"@message":     "There was an error connecting to HCP Terraform. Please do not exit\nTerraform to prevent data loss! Trying to restore the connection...",
+				"message_code": "initial_retry_error_message",
+				"@module":      "terraform.ui",
+				"type":         "cloud_output",
+			},
+		}
+		actual := done(t).Stdout()
+		testJSONViewOutputEqualsFull(t, actual, want)
+	})
+
+	t.Run("subsequent retry with elapsed time", func(t *testing.T) {
+		streams, done := terminal.StreamsForTesting(t)
+		newCloud := NewCloud(arguments.ViewJSON, NewView(streams).SetRunningInAutomation(true))
+		cloudJSON, ok := newCloud.(*CloudJSON)
+		if !ok {
+			t.Fatalf("unexpected return type %T", newCloud)
+		}
+
+		cloudJSON.lastRetry = time.Now().Add(-2 * time.Second) // Simulate a delay of 2 seconds
+		cloudJSON.RetryLog(2, &http.Response{StatusCode: 500})
+
+		version := tfversion.String()
+		want := []map[string]interface{}{
+			{
+				"@level":    "info",
+				"@message":  fmt.Sprintf("Terraform %s", version),
+				"@module":   "terraform.ui",
+				"terraform": version,
+				"type":      "version",
+				"ui":        JSON_UI_VERSION,
+			},
+			{
+				"@level":       "info",
+				"@message":     "Still trying to restore the connection... (2s elapsed)",
+				"message_code": "repeated_retry_error_message",
+				"@module":      "terraform.ui",
+				"type":         "cloud_output",
+			},
+		}
+
+		actual := done(t).Stdout()
+		testJSONViewOutputEqualsFull(t, actual, want)
+	})
+
+	t.Run("retry with 429 status, no output", func(t *testing.T) {
+		streams, done := terminal.StreamsForTesting(t)
+		newCloud := NewCloud(arguments.ViewJSON, NewView(streams).SetRunningInAutomation(true))
+		cloudJSON, ok := newCloud.(*CloudJSON)
+		if !ok {
+			t.Fatalf("unexpected return type %T", newCloud)
+		}
+
+		cloudJSON.RetryLog(0, &http.Response{
+			StatusCode: http.StatusTooManyRequests, // HTTP: 429
+		})
+
+		version := tfversion.String()
+		want := []map[string]interface{}{
+			{
+				"@level":    "info",
+				"@message":  fmt.Sprintf("Terraform %s", version),
+				"@module":   "terraform.ui",
+				"terraform": version,
+				"type":      "version",
+				"ui":        JSON_UI_VERSION,
+			},
+		}
+		actual := done(t).Stdout()
+		testJSONViewOutputEqualsFull(t, actual, want)
+	})
+}
+
 func TestNewCloud_jsonViewOutput(t *testing.T) {
 	t.Run("no param", func(t *testing.T) {
 		streams, done := terminal.StreamsForTesting(t)
@@ -172,24 +339,6 @@ func TestNewCloud_jsonViewOutput(t *testing.T) {
 	})
 }
 
-func TestNewCloud_jsonViewPrepareMessage(t *testing.T) {
-	t.Run("existing message code", func(t *testing.T) {
-		streams, _ := terminal.StreamsForTesting(t)
-
-		newCloud := NewCloud(arguments.ViewJSON, NewView(streams).SetRunningInAutomation(true))
-		if _, ok := newCloud.(*CloudJSON); !ok {
-			t.Fatalf("unexpected return type %t", newCloud)
-		}
-
-		want := "There was an error connecting to HCP Terraform. Please do not exit\nTerraform to prevent data loss! Trying to restore the connection..."
-
-		actual := newCloud.PrepareMessage(InitialRetryErrorMessage)
-		if !cmp.Equal(want, actual) {
-			t.Errorf("unexpected output: %s", cmp.Diff(want, actual))
-		}
-	})
-}
-
 func TestNewCloud_jsonViewDiagnostics(t *testing.T) {
 	streams, done := terminal.StreamsForTesting(t)