diff --git a/internal/configs/checks.go b/internal/configs/checks.go
index 0980ec16c..10ad62b69 100644
--- a/internal/configs/checks.go
+++ b/internal/configs/checks.go
@@ -2,10 +2,8 @@ package configs
 
 import (
 	"fmt"
-	"unicode"
 
 	"github.com/hashicorp/hcl/v2"
-	"github.com/hashicorp/hcl/v2/gohcl"
 	"github.com/hashicorp/terraform/internal/addrs"
 	"github.com/hashicorp/terraform/internal/lang"
 )
@@ -24,12 +22,15 @@ type CheckRule struct {
 	// input variables can only refer to the variable that is being validated.
 	Condition hcl.Expression
 
-	// ErrorMessage is one or more full sentences, which would need to be in
+	// ErrorMessage should be one or more full sentences, which should be in
 	// English for consistency with the rest of the error message output but
-	// can in practice be in any language as long as it ends with a period.
-	// The message should describe what is required for the condition to return
-	// true in a way that would make sense to a caller of the module.
-	ErrorMessage string
+	// can in practice be in any language. The message should describe what is
+	// required for the condition to return true in a way that would make sense
+	// to a caller of the module.
+	//
+	// The error message expression has the same variables available for
+	// interpolation as the corresponding condition.
+	ErrorMessage hcl.Expression
 
 	DeclRange hcl.Range
 }
@@ -111,77 +112,12 @@ func decodeCheckRuleBlock(block *hcl.Block, override bool) (*CheckRule, hcl.Diag
 	}
 
 	if attr, exists := content.Attributes["error_message"]; exists {
-		moreDiags := gohcl.DecodeExpression(attr.Expr, nil, &cr.ErrorMessage)
-		diags = append(diags, moreDiags...)
-		if !moreDiags.HasErrors() {
-			const errSummary = "Invalid validation error message"
-			switch {
-			case cr.ErrorMessage == "":
-				diags = diags.Append(&hcl.Diagnostic{
-					Severity: hcl.DiagError,
-					Summary:  errSummary,
-					Detail:   "An empty string is not a valid nor useful error message.",
-					Subject:  attr.Expr.Range().Ptr(),
-				})
-			case !looksLikeSentences(cr.ErrorMessage):
-				// Because we're going to include this string verbatim as part
-				// of a bigger error message written in our usual style in
-				// English, we'll require the given error message to conform
-				// to that. We might relax this in future if e.g. we start
-				// presenting these error messages in a different way, or if
-				// Terraform starts supporting producing error messages in
-				// other human languages, etc.
-				// For pragmatism we also allow sentences ending with
-				// exclamation points, but we don't mention it explicitly here
-				// because that's not really consistent with the Terraform UI
-				// writing style.
-				diags = diags.Append(&hcl.Diagnostic{
-					Severity: hcl.DiagError,
-					Summary:  errSummary,
-					Detail:   "The validation error message must be at least one full sentence starting with an uppercase letter and ending with a period or question mark.\n\nYour given message will be included as part of a larger Terraform error message, written as English prose. For broadly-shared modules we suggest using a similar writing style so that the overall result will be consistent.",
-					Subject:  attr.Expr.Range().Ptr(),
-				})
-			}
-		}
+		cr.ErrorMessage = attr.Expr
 	}
 
 	return cr, diags
 }
 
-// looksLikeSentence is a simple heuristic that encourages writing error
-// messages that will be presentable when included as part of a larger
-// Terraform error diagnostic whose other text is written in the Terraform
-// UI writing style.
-//
-// This is intentionally not a very strong validation since we're assuming
-// that module authors want to write good messages and might just need a nudge
-// about Terraform's specific style, rather than that they are going to try
-// to work around these rules to write a lower-quality message.
-func looksLikeSentences(s string) bool {
-	if len(s) < 1 {
-		return false
-	}
-	runes := []rune(s) // HCL guarantees that all strings are valid UTF-8
-	first := runes[0]
-	last := runes[len(runes)-1]
-
-	// If the first rune is a letter then it must be an uppercase letter.
-	// (This will only see the first rune in a multi-rune combining sequence,
-	// but the first rune is generally the letter if any are, and if not then
-	// we'll just ignore it because we're primarily expecting English messages
-	// right now anyway, for consistency with all of Terraform's other output.)
-	if unicode.IsLetter(first) && !unicode.IsUpper(first) {
-		return false
-	}
-
-	// The string must be at least one full sentence, which implies having
-	// sentence-ending punctuation.
-	// (This assumes that if a sentence ends with quotes then the period
-	// will be outside the quotes, which is consistent with Terraform's UI
-	// writing style.)
-	return last == '.' || last == '?' || last == '!'
-}
-
 var checkRuleBlockSchema = &hcl.BodySchema{
 	Attributes: []hcl.AttributeSchema{
 		{
diff --git a/internal/configs/named_values.go b/internal/configs/named_values.go
index 970656511..10882ac08 100644
--- a/internal/configs/named_values.go
+++ b/internal/configs/named_values.go
@@ -345,6 +345,31 @@ func decodeVariableValidationBlock(varName string, block *hcl.Block, override bo
 		}
 	}
 
+	if vv.ErrorMessage != nil {
+		// The same applies to the validation error message, except that
+		// references are not required. A string literal is a valid error
+		// message.
+		goodRefs := 0
+		for _, traversal := range vv.ErrorMessage.Variables() {
+			ref, moreDiags := addrs.ParseRef(traversal)
+			if !moreDiags.HasErrors() {
+				if addr, ok := ref.Subject.(addrs.InputVariable); ok {
+					if addr.Name == varName {
+						goodRefs++
+						continue // Reference is valid
+					}
+				}
+			}
+			// If we fall out here then the reference is invalid.
+			diags = diags.Append(&hcl.Diagnostic{
+				Severity: hcl.DiagError,
+				Summary:  "Invalid reference in variable validation",
+				Detail:   fmt.Sprintf("The error message for variable %q can only refer to the variable itself, using var.%s.", varName, varName),
+				Subject:  traversal.SourceRange().Ptr(),
+			})
+		}
+	}
+
 	return vv, diags
 }
 
diff --git a/internal/configs/named_values_test.go b/internal/configs/named_values_test.go
deleted file mode 100644
index 3a44438a4..000000000
--- a/internal/configs/named_values_test.go
+++ /dev/null
@@ -1,33 +0,0 @@
-package configs
-
-import (
-	"testing"
-)
-
-func Test_looksLikeSentences(t *testing.T) {
-	tests := map[string]struct {
-		args string
-		want bool
-	}{
-		"empty sentence": {
-			args: "",
-			want: false,
-		},
-		"valid sentence": {
-			args: "A valid sentence.",
-			want: true,
-		},
-		"valid sentence with an accent": {
-			args: `A Valid sentence with an accent "é".`,
-			want: true,
-		},
-	}
-
-	for name, tt := range tests {
-		t.Run(name, func(t *testing.T) {
-			if got := looksLikeSentences(tt.args); got != tt.want {
-				t.Errorf("looksLikeSentences() = %v, want %v", got, tt.want)
-			}
-		})
-	}
-}
diff --git a/internal/configs/testdata/invalid-files/variable-validation-bad-msg.tf b/internal/configs/testdata/invalid-files/variable-validation-bad-msg.tf
deleted file mode 100644
index 65df45579..000000000
--- a/internal/configs/testdata/invalid-files/variable-validation-bad-msg.tf
+++ /dev/null
@@ -1,6 +0,0 @@
-variable "validation" {
-  validation {
-    condition     = var.validation != 4
-    error_message = "not four" # ERROR: Invalid validation error message
-  }
-}
diff --git a/internal/configs/testdata/invalid-files/variable-validation-condition-badref.tf b/internal/configs/testdata/invalid-files/variable-validation-condition-badref.tf
index 42f4aa5f2..9b9e93576 100644
--- a/internal/configs/testdata/invalid-files/variable-validation-condition-badref.tf
+++ b/internal/configs/testdata/invalid-files/variable-validation-condition-badref.tf
@@ -9,3 +9,10 @@ variable "validation" {
     error_message = "Must be five."
   }
 }
+
+variable "validation_error_expression" {
+  validation {
+    condition     = var.validation_error_expression != 1
+    error_message = "Cannot equal ${local.foo}." # ERROR: Invalid reference in variable validation
+  }
+}
diff --git a/internal/configs/testdata/valid-files/variable_validation.tf b/internal/configs/testdata/valid-files/variable_validation.tf
index 0a0c2dd50..20e227e06 100644
--- a/internal/configs/testdata/valid-files/variable_validation.tf
+++ b/internal/configs/testdata/valid-files/variable_validation.tf
@@ -4,3 +4,19 @@ variable "validation" {
     error_message = "Must be five."
   }
 }
+
+variable "validation_function" {
+  type = list(string)
+  validation {
+    condition     = length(var.validation_function) > 0
+    error_message = "Must not be empty."
+  }
+}
+
+variable "validation_error_expression" {
+  type = list(string)
+  validation {
+    condition     = length(var.validation_error_expression) < 10
+    error_message = "Too long (${length(var.validation_error_expression)} is greater than 10)."
+  }
+}
diff --git a/internal/terraform/context_plan2_test.go b/internal/terraform/context_plan2_test.go
index 622c4c803..ba153230c 100644
--- a/internal/terraform/context_plan2_test.go
+++ b/internal/terraform/context_plan2_test.go
@@ -2561,7 +2561,7 @@ func TestContext2Plan_preconditionErrors(t *testing.T) {
 		{
 			"test_resource.c.value",
 			"Invalid condition result",
-			"Invalid validation condition result value: a bool is required",
+			"Invalid condition result value: a bool is required",
 		},
 	}
 
diff --git a/internal/terraform/context_validate_test.go b/internal/terraform/context_validate_test.go
index 1f0491f1a..c049b17ce 100644
--- a/internal/terraform/context_validate_test.go
+++ b/internal/terraform/context_validate_test.go
@@ -2095,3 +2095,293 @@ func TestContext2Validate_nonNullableVariableDefaultValidation(t *testing.T) {
 		t.Fatal(diags.ErrWithWarnings())
 	}
 }
+
+func TestContext2Validate_precondition_good(t *testing.T) {
+	p := testProvider("aws")
+	p.GetProviderSchemaResponse = getProviderSchemaResponseFromProviderSchema(&ProviderSchema{
+		ResourceTypes: map[string]*configschema.Block{
+			"aws_instance": {
+				Attributes: map[string]*configschema.Attribute{
+					"foo": {Type: cty.String, Optional: true},
+				},
+			},
+		},
+	})
+	m := testModuleInline(t, map[string]string{
+		"main.tf": `
+terraform {
+  experiments = [preconditions_postconditions]
+}
+
+variable "input" {
+  type    = string
+  default = "foo"
+}
+
+resource "aws_instance" "test" {
+  foo = var.input
+
+  lifecycle {
+    precondition {
+      condition     = length(var.input) > 0
+      error_message = "Input cannot be empty."
+    }
+  }
+}
+ `,
+	})
+
+	ctx := testContext2(t, &ContextOpts{
+		Providers: map[addrs.Provider]providers.Factory{
+			addrs.NewDefaultProvider("aws"): testProviderFuncFixed(p),
+		},
+	})
+
+	diags := ctx.Validate(m)
+	if diags.HasErrors() {
+		t.Fatal(diags.ErrWithWarnings())
+	}
+}
+
+func TestContext2Validate_precondition_badCondition(t *testing.T) {
+	p := testProvider("aws")
+	p.GetProviderSchemaResponse = getProviderSchemaResponseFromProviderSchema(&ProviderSchema{
+		ResourceTypes: map[string]*configschema.Block{
+			"aws_instance": {
+				Attributes: map[string]*configschema.Attribute{
+					"foo": {Type: cty.String, Optional: true},
+				},
+			},
+		},
+	})
+	m := testModuleInline(t, map[string]string{
+		"main.tf": `
+terraform {
+  experiments = [preconditions_postconditions]
+}
+
+variable "input" {
+  type    = string
+  default = "foo"
+}
+
+resource "aws_instance" "test" {
+  foo = var.input
+
+  lifecycle {
+    precondition {
+      condition     = length(one(var.input)) == 1
+      error_message = "You can't do that."
+    }
+  }
+}
+ `,
+	})
+
+	ctx := testContext2(t, &ContextOpts{
+		Providers: map[addrs.Provider]providers.Factory{
+			addrs.NewDefaultProvider("aws"): testProviderFuncFixed(p),
+		},
+	})
+
+	diags := ctx.Validate(m)
+	if !diags.HasErrors() {
+		t.Fatalf("succeeded; want error")
+	}
+	if got, want := diags.Err().Error(), "Invalid function argument"; !strings.Contains(got, want) {
+		t.Errorf("unexpected error.\ngot: %s\nshould contain: %q", got, want)
+	}
+}
+
+func TestContext2Validate_precondition_badErrorMessage(t *testing.T) {
+	p := testProvider("aws")
+	p.GetProviderSchemaResponse = getProviderSchemaResponseFromProviderSchema(&ProviderSchema{
+		ResourceTypes: map[string]*configschema.Block{
+			"aws_instance": {
+				Attributes: map[string]*configschema.Attribute{
+					"foo": {Type: cty.String, Optional: true},
+				},
+			},
+		},
+	})
+	m := testModuleInline(t, map[string]string{
+		"main.tf": `
+terraform {
+  experiments = [preconditions_postconditions]
+}
+
+variable "input" {
+  type    = string
+  default = "foo"
+}
+
+resource "aws_instance" "test" {
+  foo = var.input
+
+  lifecycle {
+    precondition {
+      condition     = var.input != "foo"
+      error_message = "This is a bad use of a function: ${one(var.input)}."
+    }
+  }
+}
+ `,
+	})
+
+	ctx := testContext2(t, &ContextOpts{
+		Providers: map[addrs.Provider]providers.Factory{
+			addrs.NewDefaultProvider("aws"): testProviderFuncFixed(p),
+		},
+	})
+
+	diags := ctx.Validate(m)
+	if !diags.HasErrors() {
+		t.Fatalf("succeeded; want error")
+	}
+	if got, want := diags.Err().Error(), "Invalid function argument"; !strings.Contains(got, want) {
+		t.Errorf("unexpected error.\ngot: %s\nshould contain: %q", got, want)
+	}
+}
+
+func TestContext2Validate_postcondition_good(t *testing.T) {
+	p := testProvider("aws")
+	p.GetProviderSchemaResponse = getProviderSchemaResponseFromProviderSchema(&ProviderSchema{
+		ResourceTypes: map[string]*configschema.Block{
+			"aws_instance": {
+				Attributes: map[string]*configschema.Attribute{
+					"foo": {Type: cty.String, Optional: true},
+				},
+			},
+		},
+	})
+	m := testModuleInline(t, map[string]string{
+		"main.tf": `
+terraform {
+  experiments = [preconditions_postconditions]
+}
+
+resource "aws_instance" "test" {
+  foo = "foo"
+
+  lifecycle {
+    postcondition {
+      condition     = length(self.foo) > 0
+      error_message = "Input cannot be empty."
+    }
+  }
+}
+ `,
+	})
+
+	ctx := testContext2(t, &ContextOpts{
+		Providers: map[addrs.Provider]providers.Factory{
+			addrs.NewDefaultProvider("aws"): testProviderFuncFixed(p),
+		},
+	})
+
+	diags := ctx.Validate(m)
+	if diags.HasErrors() {
+		t.Fatal(diags.ErrWithWarnings())
+	}
+}
+
+func TestContext2Validate_postcondition_badCondition(t *testing.T) {
+	p := testProvider("aws")
+	p.GetProviderSchemaResponse = getProviderSchemaResponseFromProviderSchema(&ProviderSchema{
+		ResourceTypes: map[string]*configschema.Block{
+			"aws_instance": {
+				Attributes: map[string]*configschema.Attribute{
+					"foo": {Type: cty.String, Optional: true},
+				},
+			},
+		},
+	})
+	// This postcondition's condition expression does not refer to self, which
+	// is unrealistic. This is because at the time of writing the test, self is
+	// always an unknown value of dynamic type during validation. As a result,
+	// validation of conditions which refer to resource arguments is not
+	// possible until plan time. For now we exercise the code by referring to
+	// an input variable.
+	m := testModuleInline(t, map[string]string{
+		"main.tf": `
+terraform {
+  experiments = [preconditions_postconditions]
+}
+
+variable "input" {
+  type    = string
+  default = "foo"
+}
+
+resource "aws_instance" "test" {
+  foo = var.input
+
+  lifecycle {
+    postcondition {
+      condition     = length(one(var.input)) == 1
+      error_message = "You can't do that."
+    }
+  }
+}
+ `,
+	})
+
+	ctx := testContext2(t, &ContextOpts{
+		Providers: map[addrs.Provider]providers.Factory{
+			addrs.NewDefaultProvider("aws"): testProviderFuncFixed(p),
+		},
+	})
+
+	diags := ctx.Validate(m)
+	if !diags.HasErrors() {
+		t.Fatalf("succeeded; want error")
+	}
+	if got, want := diags.Err().Error(), "Invalid function argument"; !strings.Contains(got, want) {
+		t.Errorf("unexpected error.\ngot: %s\nshould contain: %q", got, want)
+	}
+}
+
+func TestContext2Validate_postcondition_badErrorMessage(t *testing.T) {
+	p := testProvider("aws")
+	p.GetProviderSchemaResponse = getProviderSchemaResponseFromProviderSchema(&ProviderSchema{
+		ResourceTypes: map[string]*configschema.Block{
+			"aws_instance": {
+				Attributes: map[string]*configschema.Attribute{
+					"foo": {Type: cty.String, Optional: true},
+				},
+			},
+		},
+	})
+	m := testModuleInline(t, map[string]string{
+		"main.tf": `
+terraform {
+  experiments = [preconditions_postconditions]
+}
+
+resource "aws_instance" "test" {
+  foo = "foo"
+
+  lifecycle {
+    postcondition {
+      condition     = self.foo != "foo"
+      error_message = "This is a bad use of a function: ${one("foo")}."
+    }
+  }
+}
+ `,
+	})
+
+	ctx := testContext2(t, &ContextOpts{
+		Providers: map[addrs.Provider]providers.Factory{
+			addrs.NewDefaultProvider("aws"): testProviderFuncFixed(p),
+		},
+	})
+
+	diags := ctx.Validate(m)
+	if !diags.HasErrors() {
+		t.Fatalf("succeeded; want error")
+	}
+	if got, want := diags.Err().Error(), "Invalid function argument"; !strings.Contains(got, want) {
+		t.Errorf("unexpected error.\ngot: %s\nshould contain: %q", got, want)
+	}
+}
diff --git a/internal/terraform/eval_conditions.go b/internal/terraform/eval_conditions.go
index 302f88160..ad4d0cc4d 100644
--- a/internal/terraform/eval_conditions.go
+++ b/internal/terraform/eval_conditions.go
@@ -3,6 +3,7 @@ package terraform
 import (
 	"fmt"
 	"log"
+	"strings"
 
 	"github.com/hashicorp/hcl/v2"
 	"github.com/zclconf/go-cty/cty"
@@ -59,12 +60,20 @@ func evalCheckRules(typ checkType, rules []*configs.CheckRule, ctx EvalContext,
 
 		refs, moreDiags := lang.ReferencesInExpr(rule.Condition)
 		ruleDiags = ruleDiags.Append(moreDiags)
+		moreRefs, moreDiags := lang.ReferencesInExpr(rule.ErrorMessage)
+		ruleDiags = ruleDiags.Append(moreDiags)
+		refs = append(refs, moreRefs...)
+
 		scope := ctx.EvaluationScope(self, keyData)
 		hclCtx, moreDiags := scope.EvalContext(refs)
 		ruleDiags = ruleDiags.Append(moreDiags)
 
 		result, hclDiags := rule.Condition.Value(hclCtx)
 		ruleDiags = ruleDiags.Append(hclDiags)
+
+		errorValue, errorDiags := rule.ErrorMessage.Value(hclCtx)
+		ruleDiags = ruleDiags.Append(errorDiags)
+
 		diags = diags.Append(ruleDiags)
 
 		if ruleDiags.HasErrors() {
@@ -91,7 +100,7 @@ func evalCheckRules(typ checkType, rules []*configs.CheckRule, ctx EvalContext,
 			diags = diags.Append(&hcl.Diagnostic{
 				Severity:    hcl.DiagError,
 				Summary:     errInvalidCondition,
-				Detail:      fmt.Sprintf("Invalid validation condition result value: %s.", tfdiags.FormatError(err)),
+				Detail:      fmt.Sprintf("Invalid condition result value: %s.", tfdiags.FormatError(err)),
 				Subject:     rule.Condition.Range().Ptr(),
 				Expression:  rule.Condition,
 				EvalContext: hclCtx,
@@ -99,16 +108,38 @@ func evalCheckRules(typ checkType, rules []*configs.CheckRule, ctx EvalContext,
 			continue
 		}
 
-		if result.False() {
-			diags = diags.Append(&hcl.Diagnostic{
-				Severity:    hcl.DiagError,
-				Summary:     typ.FailureSummary(),
-				Detail:      rule.ErrorMessage,
-				Subject:     rule.Condition.Range().Ptr(),
-				Expression:  rule.Condition,
-				EvalContext: hclCtx,
-			})
+		if result.True() {
+			continue
 		}
+
+		var errorMessage string
+		if !errorDiags.HasErrors() && errorValue.IsKnown() && !errorValue.IsNull() {
+			var err error
+			errorValue, err = convert.Convert(errorValue, cty.String)
+			if err != nil {
+				diags = diags.Append(&hcl.Diagnostic{
+					Severity:    hcl.DiagError,
+					Summary:     "Invalid error message",
+					Detail:      fmt.Sprintf("Unsuitable value for error message: %s.", tfdiags.FormatError(err)),
+					Subject:     rule.ErrorMessage.Range().Ptr(),
+					Expression:  rule.ErrorMessage,
+					EvalContext: hclCtx,
+				})
+			} else {
+				errorMessage = strings.TrimSpace(errorValue.AsString())
+			}
+		}
+		if errorMessage == "" {
+			errorMessage = "Failed to evaluate condition error message."
+		}
+		diags = diags.Append(&hcl.Diagnostic{
+			Severity:    hcl.DiagError,
+			Summary:     typ.FailureSummary(),
+			Detail:      errorMessage,
+			Subject:     rule.Condition.Range().Ptr(),
+			Expression:  rule.Condition,
+			EvalContext: hclCtx,
+		})
 	}
 
 	return diags
diff --git a/internal/terraform/eval_variable.go b/internal/terraform/eval_variable.go
index fd57a136f..629da7051 100644
--- a/internal/terraform/eval_variable.go
+++ b/internal/terraform/eval_variable.go
@@ -3,8 +3,10 @@ package terraform
 import (
 	"fmt"
 	"log"
+	"strings"
 
 	"github.com/hashicorp/hcl/v2"
+	"github.com/hashicorp/hcl/v2/gohcl"
 	"github.com/hashicorp/terraform/internal/addrs"
 	"github.com/hashicorp/terraform/internal/configs"
 	"github.com/hashicorp/terraform/internal/tfdiags"
@@ -205,11 +207,67 @@ func evalVariableValidations(addr addrs.AbsInputVariableInstance, config *config
 	for _, validation := range config.Validations {
 		const errInvalidCondition = "Invalid variable validation result"
 		const errInvalidValue = "Invalid value for variable"
+		var ruleDiags tfdiags.Diagnostics
 
 		result, moreDiags := validation.Condition.Value(hclCtx)
-		diags = diags.Append(moreDiags)
-		if moreDiags.HasErrors() {
-			log.Printf("[TRACE] evalVariableValidations: %s rule %s condition expression failed: %s", addr, validation.DeclRange, diags.Err().Error())
+		ruleDiags = ruleDiags.Append(moreDiags)
+		errorValue, errorDiags := validation.ErrorMessage.Value(hclCtx)
+
+		// The following error handling is a workaround to preserve backwards
+		// compatibility. Due to an implementation quirk, all prior versions of
+		// Terraform would treat error messages specified using JSON
+		// configuration syntax (.tf.json) as string literals, even if they
+		// contained the "${" template expression operator. This behaviour did
+		// not match that of HCL configuration syntax, where a template
+		// expression would result in a validation error.
+		//
+		// As a result, users writing or generating JSON configuration syntax
+		// may have specified error messages which are invalid template
+		// expressions. As we add support for error message expressions, we are
+		// unable to perfectly distinguish between these two cases.
+		//
+		// To ensure that we don't break backwards compatibility, we have the
+		// below fallback logic if the error message fails to evaluate. This
+		// should only have any effect for JSON configurations. The gohcl
+		// DecodeExpression function behaves differently when the source of the
+		// expression is a JSON configuration file and a nil context is passed.
+		if errorDiags.HasErrors() {
+			// Attempt to decode the expression as a string literal. Passing
+			// nil as the context forces a JSON syntax string value to be
+			// interpreted as a string literal.
+			var errorString string
+			moreErrorDiags := gohcl.DecodeExpression(validation.ErrorMessage, nil, &errorString)
+			if !moreErrorDiags.HasErrors() {
+				// Decoding succeeded, meaning that this is a JSON syntax
+				// string value. We rewrap that as a cty value to allow later
+				// decoding to succeed.
+				errorValue = cty.StringVal(errorString)
+
+				// This warning diagnostic explains this odd behaviour, while
+				// giving us an escape hatch to change this to a hard failure
+				// in some future Terraform 1.x version.
+				errorDiags = hcl.Diagnostics{
+					&hcl.Diagnostic{
+						Severity:    hcl.DiagWarning,
+						Summary:     "Validation error message expression is invalid",
+						Detail:      fmt.Sprintf("The error message provided could not be evaluated as an expression, so Terraform is interpreting it as a string literal.\n\nIn future versions of Terraform, this will be considered an error. Please file a GitHub issue if this would break your workflow.\n\n%s", errorDiags.Error()),
+						Subject:     validation.ErrorMessage.Range().Ptr(),
+						Context:     validation.DeclRange.Ptr(),
+						Expression:  validation.ErrorMessage,
+						EvalContext: hclCtx,
+					},
+				}
+			}
+
+			// We want to either report the original diagnostics if the
+			// fallback failed, or the warning generated above if it succeeded.
+			ruleDiags = ruleDiags.Append(errorDiags)
+		}
+
+		diags = diags.Append(ruleDiags)
+
+		if ruleDiags.HasErrors() {
+			log.Printf("[TRACE] evalVariableValidations: %s rule %s check rule evaluation failed: %s", addr, validation.DeclRange, ruleDiags.Err().Error())
 		}
 		if !result.IsKnown() {
 			log.Printf("[TRACE] evalVariableValidations: %s rule %s condition value is unknown, so skipping validation for now", addr, validation.DeclRange)
@@ -245,26 +303,53 @@ func evalVariableValidations(addr addrs.AbsInputVariableInstance, config *config
 		// we discard the marks now.
 		result, _ = result.Unmark()
 
-		if result.False() {
-			if expr != nil {
+		if result.True() {
+			continue
+		}
+
+		var errorMessage string
+		if !errorDiags.HasErrors() && errorValue.IsKnown() && !errorValue.IsNull() {
+			var err error
+			errorValue, err = convert.Convert(errorValue, cty.String)
+			if err != nil {
 				diags = diags.Append(&hcl.Diagnostic{
-					Severity: hcl.DiagError,
-					Summary:  errInvalidValue,
-					Detail:   fmt.Sprintf("%s\n\nThis was checked by the validation rule at %s.", validation.ErrorMessage, validation.DeclRange.String()),
-					Subject:  expr.Range().Ptr(),
+					Severity:    hcl.DiagError,
+					Summary:     "Invalid error message",
+					Detail:      fmt.Sprintf("Unsuitable value for error message: %s.", tfdiags.FormatError(err)),
+					Subject:     validation.ErrorMessage.Range().Ptr(),
+					Expression:  validation.ErrorMessage,
+					EvalContext: hclCtx,
 				})
 			} else {
-				// Since we don't have a source expression for a root module
-				// variable, we'll just report the error from the perspective
-				// of the variable declaration itself.
-				diags = diags.Append(&hcl.Diagnostic{
-					Severity: hcl.DiagError,
-					Summary:  errInvalidValue,
-					Detail:   fmt.Sprintf("%s\n\nThis was checked by the validation rule at %s.", validation.ErrorMessage, validation.DeclRange.String()),
-					Subject:  config.DeclRange.Ptr(),
-				})
+				errorMessage = strings.TrimSpace(errorValue.AsString())
 			}
 		}
+		if errorMessage == "" {
+			errorMessage = "Failed to evaluate condition error message."
+		}
+
+		if expr != nil {
+			diags = diags.Append(&hcl.Diagnostic{
+				Severity:    hcl.DiagError,
+				Summary:     errInvalidValue,
+				Detail:      fmt.Sprintf("%s\n\nThis was checked by the validation rule at %s.", errorMessage, validation.DeclRange.String()),
+				Subject:     expr.Range().Ptr(),
+				Expression:  validation.Condition,
+				EvalContext: hclCtx,
+			})
+		} else {
+			// Since we don't have a source expression for a root module
+			// variable, we'll just report the error from the perspective
+			// of the variable declaration itself.
+			diags = diags.Append(&hcl.Diagnostic{
+				Severity:    hcl.DiagError,
+				Summary:     errInvalidValue,
+				Detail:      fmt.Sprintf("%s\n\nThis was checked by the validation rule at %s.", errorMessage, validation.DeclRange.String()),
+				Subject:     config.DeclRange.Ptr(),
+				Expression:  validation.Condition,
+				EvalContext: hclCtx,
+			})
+		}
 	}
 
 	return diags
diff --git a/internal/terraform/eval_variable_test.go b/internal/terraform/eval_variable_test.go
index 0ebea982f..c84a969e8 100644
--- a/internal/terraform/eval_variable_test.go
+++ b/internal/terraform/eval_variable_test.go
@@ -2,12 +2,14 @@ package terraform
 
 import (
 	"fmt"
+	"strings"
 	"testing"
 
 	"github.com/hashicorp/hcl/v2"
 	"github.com/zclconf/go-cty/cty"
 
 	"github.com/hashicorp/terraform/internal/addrs"
+	"github.com/hashicorp/terraform/internal/lang"
 	"github.com/hashicorp/terraform/internal/tfdiags"
 )
 
@@ -561,3 +563,155 @@ func TestPrepareFinalInputVariableValue(t *testing.T) {
 		}
 	})
 }
+
+// These tests cover the JSON syntax configuration edge case handling,
+// the background of which is described in detail in comments in the
+// evalVariableValidations function. Future versions of Terraform may
+// be able to remove this behaviour altogether.
+func TestEvalVariableValidations_jsonErrorMessageEdgeCase(t *testing.T) {
+	cfgSrc := `{
+  "variable": {
+    "valid": {
+      "type": "string",
+      "validation": {
+        "condition": "${var.valid != \"bar\"}",
+        "error_message": "Valid template string ${var.valid}"
+      }
+    },
+    "invalid": {
+      "type": "string",
+      "validation": {
+        "condition": "${var.invalid != \"bar\"}",
+        "error_message": "Invalid template string ${"
+      }
+    }
+  }
+}
+`
+	cfg := testModuleInline(t, map[string]string{
+		"main.tf.json": cfgSrc,
+	})
+	variableConfigs := cfg.Module.Variables
+
+	// Because we loaded our pseudo-module from a temporary file, the
+	// declaration source ranges will have unpredictable filenames. We'll
+	// fix that here just to make things easier below.
+	for _, vc := range variableConfigs {
+		vc.DeclRange.Filename = "main.tf.json"
+		for _, v := range vc.Validations {
+			v.DeclRange.Filename = "main.tf.json"
+		}
+	}
+
+	tests := []struct {
+		varName  string
+		given    cty.Value
+		wantErr  []string
+		wantWarn []string
+	}{
+		// Valid variable validation declaration, assigned value which passes
+		// the condition generates no diagnostics.
+		{
+			varName: "valid",
+			given:   cty.StringVal("foo"),
+		},
+		// Assigning a value which fails the condition generates an error
+		// message with the expression successfully evaluated.
+		{
+			varName: "valid",
+			given:   cty.StringVal("bar"),
+			wantErr: []string{
+				"Invalid value for variable",
+				"Valid template string bar",
+			},
+		},
+		// Invalid variable validation declaration due to an unparseable
+		// template string. Assigning a value which passes the condition
+		// results in a warning about the error message.
+		{
+			varName: "invalid",
+			given:   cty.StringVal("foo"),
+			wantWarn: []string{
+				"Validation error message expression is invalid",
+				"Missing expression; Expected the start of an expression, but found the end of the file.",
+			},
+		},
+		// Assigning a value which fails the condition generates an error
+		// message including the configured string interpreted as a literal
+		// value, and the same warning diagnostic as above.
+		{
+			varName: "invalid",
+			given:   cty.StringVal("bar"),
+			wantErr: []string{
+				"Invalid value for variable",
+				"Invalid template string ${",
+			},
+			wantWarn: []string{
+				"Validation error message expression is invalid",
+				"Missing expression; Expected the start of an expression, but found the end of the file.",
+			},
+		},
+	}
+
+	for _, test := range tests {
+		t.Run(fmt.Sprintf("%s %#v", test.varName, test.given), func(t *testing.T) {
+			varAddr := addrs.InputVariable{Name: test.varName}.Absolute(addrs.RootModuleInstance)
+			varCfg := variableConfigs[test.varName]
+			if varCfg == nil {
+				t.Fatalf("invalid variable name %q", test.varName)
+			}
+
+			// Build a mock context to allow the function under test to
+			// retrieve the variable value and evaluate the expressions
+			ctx := &MockEvalContext{}
+
+			// We need a minimal scope to allow basic functions to be passed to
+			// the HCL scope
+			ctx.EvaluationScopeScope = &lang.Scope{}
+			ctx.GetVariableValueFunc = func(addr addrs.AbsInputVariableInstance) cty.Value {
+				if got, want := addr.String(), varAddr.String(); got != want {
+					t.Errorf("incorrect argument to GetVariableValue: got %s, want %s", got, want)
+				}
+				return test.given
+			}
+
+			gotDiags := evalVariableValidations(
+				varAddr, varCfg, nil, ctx,
+			)
+
+			if len(test.wantErr) == 0 && len(test.wantWarn) == 0 {
+				if len(gotDiags) > 0 {
+					t.Errorf("no diags expected, got %s", gotDiags.Err().Error())
+				}
+			} else {
+			wantErrs:
+				for _, want := range test.wantErr {
+					for _, diag := range gotDiags {
+						if diag.Severity() != tfdiags.Error {
+							continue
+						}
+						desc := diag.Description()
+						if strings.Contains(desc.Summary, want) || strings.Contains(desc.Detail, want) {
+							continue wantErrs
+						}
+					}
+					t.Errorf("no error diagnostics found containing %q\ngot: %s", want, gotDiags.Err().Error())
+				}
+
+			wantWarns:
+				for _, want := range test.wantWarn {
+					for _, diag := range gotDiags {
+						if diag.Severity() != tfdiags.Warning {
+							continue
+						}
+						desc := diag.Description()
+						if strings.Contains(desc.Summary, want) || strings.Contains(desc.Detail, want) {
+							continue wantWarns
+						}
+					}
+					t.Errorf("no warning diagnostics found containing %q\ngot: %s", want, gotDiags.Err().Error())
+				}
+			}
+		})
+	}
+}
diff --git a/internal/terraform/node_resource_abstract.go b/internal/terraform/node_resource_abstract.go
index bc22d4be7..a15214b79 100644
--- a/internal/terraform/node_resource_abstract.go
+++ b/internal/terraform/node_resource_abstract.go
@@ -176,10 +176,14 @@ func (n *NodeAbstractResource) References() []*addrs.Reference {
 		for _, check := range c.Preconditions {
 			refs, _ := lang.ReferencesInExpr(check.Condition)
 			result = append(result, refs...)
+			refs, _ = lang.ReferencesInExpr(check.ErrorMessage)
+			result = append(result, refs...)
 		}
 		for _, check := range c.Postconditions {
 			refs, _ := lang.ReferencesInExpr(check.Condition)
 			result = append(result, refs...)
+			refs, _ = lang.ReferencesInExpr(check.ErrorMessage)
+			result = append(result, refs...)
 		}
 
 		return result
diff --git a/internal/terraform/node_resource_validate.go b/internal/terraform/node_resource_validate.go
index f3eda571e..4f316906d 100644
--- a/internal/terraform/node_resource_validate.go
+++ b/internal/terraform/node_resource_validate.go
@@ -41,6 +41,18 @@ func (n *NodeValidatableResource) Path() addrs.ModuleInstance {
 func (n *NodeValidatableResource) Execute(ctx EvalContext, op walkOperation) (diags tfdiags.Diagnostics) {
 	diags = diags.Append(n.validateResource(ctx))
 
+	var self addrs.Referenceable
+	switch {
+	case n.Config.Count != nil:
+		self = n.Addr.Resource.Instance(addrs.IntKey(0))
+	case n.Config.ForEach != nil:
+		self = n.Addr.Resource.Instance(addrs.StringKey(""))
+	default:
+		self = n.Addr.Resource.Instance(addrs.NoKey)
+	}
+	diags = diags.Append(validateCheckRules(ctx, n.Config.Preconditions, nil))
+	diags = diags.Append(validateCheckRules(ctx, n.Config.Postconditions, self))
+
 	if managed := n.Config.Managed; managed != nil {
 		hasCount := n.Config.Count != nil
 		hasForEach := n.Config.ForEach != nil
@@ -466,6 +478,20 @@ func (n *NodeValidatableResource) validateResource(ctx EvalContext) tfdiags.Diag
 	return diags
 }
 
+func validateCheckRules(ctx EvalContext, crs []*configs.CheckRule, self addrs.Referenceable) tfdiags.Diagnostics {
+	var diags tfdiags.Diagnostics
+
+	for _, cr := range crs {
+		_, conditionDiags := ctx.EvaluateExpr(cr.Condition, cty.Bool, self)
+		diags = diags.Append(conditionDiags)
+
+		_, errorMessageDiags := ctx.EvaluateExpr(cr.ErrorMessage, cty.String, self)
+		diags = diags.Append(errorMessageDiags)
+	}
+
+	return diags
+}
+
 func validateCount(ctx EvalContext, expr hcl.Expression) (diags tfdiags.Diagnostics) {
 	val, countDiags := evaluateCountExpressionValue(expr, ctx)
 	// If the value isn't known then that's the best we can do for now, but
diff --git a/internal/terraform/node_root_variable_test.go b/internal/terraform/node_root_variable_test.go
index ccf3b3e41..537cecce9 100644
--- a/internal/terraform/node_root_variable_test.go
+++ b/internal/terraform/node_root_variable_test.go
@@ -4,6 +4,7 @@ import (
 	"testing"
 
 	"github.com/hashicorp/hcl/v2"
+	"github.com/hashicorp/hcl/v2/hcltest"
 	"github.com/zclconf/go-cty/cty"
 
 	"github.com/hashicorp/terraform/internal/addrs"
@@ -101,7 +102,7 @@ func TestNodeRootVariableExecute(t *testing.T) {
 							}
 							return cty.True, nil
 						}),
-						ErrorMessage: "Must be a number.",
+						ErrorMessage: hcltest.MockExprLiteral(cty.StringVal("Must be a number.")),
 					},
 				},
 			},
diff --git a/website/docs/language/expressions/preconditions-postconditions.mdx b/website/docs/language/expressions/preconditions-postconditions.mdx
index 1aebff3b7..635cb1b63 100644
--- a/website/docs/language/expressions/preconditions-postconditions.mdx
+++ b/website/docs/language/expressions/preconditions-postconditions.mdx
@@ -335,11 +335,15 @@ Error: Resource postcondition failed
 The selected AMI must be tagged with the Component value "nomad-server".
 ```
 
-The `error_message` argument must always be a literal string, and should
-typically be written as a full sentence in a style similar to Terraform's own
-error messages. Terraform will show the given message alongside the name
-of the resource that detected the problem and any outside values used as part
-of the condition expression.
+The `error_message` argument can be any expression which evaluates to a string.
+This includes literal strings, heredocs, and template expressions. Multi-line
+error messages are supported, and lines with leading whitespace will not be
+word wrapped.
+
+Error message should typically be written as one or more full sentences in a
+style similar to Terraform's own error messages. Terraform will show the given
+message alongside the name of the resource that detected the problem and any
+outside values used as part of the condition expression.
 
 ## Preconditions or Postconditions?
 
diff --git a/website/docs/language/values/variables.mdx b/website/docs/language/values/variables.mdx
index 4bfe6e053..434c88a24 100644
--- a/website/docs/language/values/variables.mdx
+++ b/website/docs/language/values/variables.mdx
@@ -198,10 +198,13 @@ variable "image_id" {
 ```
 
 If `condition` evaluates to `false`, Terraform will produce an error message
-that includes the sentences given in `error_message`. The error message string
+that includes the result of the `error_message` expression. The error message
 should be at least one full sentence explaining the constraint that failed,
 using a sentence structure similar to the above examples.
 
+Error messages can be literal strings, heredocs, or template expressions. The
+only valid reference in an error message is the variable under validation.
+
 Multiple `validation` blocks can be declared in which case error messages
 will be returned for _all_ failed conditions.