diff --git a/internal/cloud/backend.go b/internal/cloud/backend.go
index 418658417..5fdd2b12c 100644
--- a/internal/cloud/backend.go
+++ b/internal/cloud/backend.go
@@ -784,25 +784,15 @@ func (b *Cloud) VerifyWorkspaceTerraformVersion(workspaceName string) tfdiags.Di
 	// Even if ignoring version conflicts, it may still be useful to call this
 	// method and warn the user about a mismatch between the local and remote
 	// Terraform versions.
-	severity := tfdiags.Error
-	if b.ignoreVersionConflict {
-		severity = tfdiags.Warning
-	}
-	suggestion := " If you're sure you want to upgrade the state, you can force Terraform to continue using the -ignore-remote-version flag. This may result in an unusable workspace."
-	if b.ignoreVersionConflict {
-		suggestion = ""
-	}
-
 	remoteVersion, err := version.NewSemver(workspace.TerraformVersion)
 	if err != nil {
+		log.Printf("[DEBUG] Invalid Terraform version (%s); will try to parse as version constraint", workspace.TerraformVersion)
+	}
+	if remoteVersion == nil {
 		// If it's not a valid version, it might be a valid version constraint:
 		remoteConstraint, err := version.NewConstraint(workspace.TerraformVersion)
 		if err != nil {
-			diags = diags.Append(tfdiags.Sourceless(
-				tfdiags.Error,
-				"Error looking up workspace",
-				fmt.Sprintf("Invalid Terraform version or version constraint: %s", err),
-			))
+			diags = diags.Append(terraformInvalidVersionOrConstraint(b.ignoreVersionConflict, workspace.TerraformVersion))
 			return diags
 		}
 
@@ -817,19 +807,7 @@ func (b *Cloud) VerifyWorkspaceTerraformVersion(workspaceName string) tfdiags.Di
 			return diags
 		}
 
-		diags = diags.Append(tfdiags.Sourceless(
-			severity,
-			"Terraform version mismatch",
-			fmt.Sprintf(
-				"The local Terraform version (%s) does not meet the version requirements for remote workspace %s/%s (%s).%s",
-				tfversion.String(),
-				b.organization,
-				workspace.Name,
-				workspace.TerraformVersion,
-				suggestion,
-			),
-		))
-
+		diags = diags.Append(terraformMismatchDiagnostic(b.ignoreVersionConflict, b.organization, workspace, tfversion.String()))
 		return diags
 	}
 
@@ -862,19 +840,7 @@ func (b *Cloud) VerifyWorkspaceTerraformVersion(workspaceName string) tfdiags.Di
 		}
 	}
 
-	diags = diags.Append(tfdiags.Sourceless(
-		severity,
-		"Terraform version mismatch",
-		fmt.Sprintf(
-			"The local Terraform version (%s) does not match the configured version for remote workspace %s/%s (%s).%s",
-			tfversion.String(),
-			b.organization,
-			workspace.Name,
-			workspace.TerraformVersion,
-			suggestion,
-		),
-	))
-
+	diags = diags.Append(terraformMismatchDiagnostic(b.ignoreVersionConflict, b.organization, workspace, tfversion.String()))
 	return diags
 }
 
diff --git a/internal/cloud/backend_test.go b/internal/cloud/backend_test.go
index 56fe9ebe1..38e4db8d6 100644
--- a/internal/cloud/backend_test.go
+++ b/internal/cloud/backend_test.go
@@ -705,7 +705,7 @@ func TestCloud_VerifyWorkspaceTerraformVersion_workspaceErrors(t *testing.T) {
 	if len(diags) != 1 {
 		t.Fatal("expected diag, but none returned")
 	}
-	if got := diags.Err().Error(); !strings.Contains(got, "Error looking up workspace: Invalid Terraform version") {
+	if got := diags.Err().Error(); !strings.Contains(got, "Terraform version error: The remote workspace specified") {
 		t.Fatalf("unexpected error: %s", got)
 	}
 }
@@ -760,7 +760,7 @@ func TestCloud_VerifyWorkspaceTerraformVersion_ignoreFlagSet(t *testing.T) {
 	if got, want := diags[0].Description().Summary, "Terraform version mismatch"; got != want {
 		t.Errorf("wrong summary: got %s, want %s", got, want)
 	}
-	wantDetail := "The local Terraform version (0.14.0) does not match the configured version for remote workspace hashicorp/app-prod (0.13.5)."
+	wantDetail := "The local Terraform version (0.14.0) does not meet the version requirements for remote workspace hashicorp/app-prod (0.13.5)."
 	if got := diags[0].Description().Detail; got != wantDetail {
 		t.Errorf("wrong summary: got %s, want %s", got, wantDetail)
 	}
diff --git a/internal/cloud/errors.go b/internal/cloud/errors.go
index 2c5910030..b51f44338 100644
--- a/internal/cloud/errors.go
+++ b/internal/cloud/errors.go
@@ -2,7 +2,9 @@ package cloud
 
 import (
 	"fmt"
+	"strings"
 
+	tfe "github.com/hashicorp/go-tfe"
 	"github.com/hashicorp/terraform/internal/tfdiags"
 	"github.com/zclconf/go-cty/cty"
 )
@@ -29,3 +31,42 @@ var (
 		cty.Path{cty.GetAttrStep{Name: "workspaces"}},
 	)
 )
+
+func terraformMismatchDiagnostic(ignoreVersionConflict bool, organization string, workspace *tfe.Workspace, tfversion string) tfdiags.Diagnostic {
+	severity := tfdiags.Error
+	if ignoreVersionConflict {
+		severity = tfdiags.Warning
+	}
+
+	suggestion := "If you're sure you want to upgrade the state, you can force Terraform to continue using the -ignore-remote-version flag. This may result in an unusable workspace."
+	if ignoreVersionConflict {
+		suggestion = ""
+	}
+
+	description := fmt.Sprintf(
+		"The local Terraform version (%s) does not meet the version requirements for remote workspace %s/%s (%s).\n\n%s",
+		tfversion,
+		organization,
+		workspace.Name,
+		workspace.TerraformVersion,
+		suggestion,
+	)
+	description = strings.TrimSpace(description)
+	return tfdiags.Sourceless(severity, "Terraform version mismatch", description)
+}
+
+func terraformInvalidVersionOrConstraint(ignoreVersionConflict bool, tfversion string) tfdiags.Diagnostic {
+	severity := tfdiags.Error
+	if ignoreVersionConflict {
+		severity = tfdiags.Warning
+	}
+
+	suggestion := "If you're sure you want to upgrade the state, you can force Terraform to continue using the -ignore-remote-version flag. This may result in an unusable workspace."
+	if ignoreVersionConflict {
+		suggestion = ""
+	}
+
+	description := fmt.Sprintf("The remote workspace specified an invalid Terraform version or version constraint: %s\n\n%s", tfversion, suggestion)
+	description = strings.TrimSpace(description)
+	return tfdiags.Sourceless(severity, "Terraform version error", description)
+}