diff --git a/cmd/readmevalidation/codermodules.go b/cmd/readmevalidation/codermodules.go
index 4c9d854d0..005a98ee8 100644
--- a/cmd/readmevalidation/codermodules.go
+++ b/cmd/readmevalidation/codermodules.go
@@ -94,6 +94,9 @@ func validateCoderModuleReadme(rm coderResourceReadme) []error {
 	for _, err := range validateCoderModuleReadmeBody(rm.body) {
 		errs = append(errs, addFilePathToError(rm.filePath, err))
 	}
+	for _, err := range validateResourceGfmAlerts(rm.body) {
+		errs = append(errs, addFilePathToError(rm.filePath, err))
+	}
 	if fmErrs := validateCoderResourceFrontmatter("modules", rm.filePath, rm.frontmatter); len(fmErrs) != 0 {
 		errs = append(errs, fmErrs...)
 	}
diff --git a/cmd/readmevalidation/coderresources.go b/cmd/readmevalidation/coderresources.go
index f7237a368..818d73c8c 100644
--- a/cmd/readmevalidation/coderresources.go
+++ b/cmd/readmevalidation/coderresources.go
@@ -1,6 +1,7 @@
 package main
 
 import (
+	"bufio"
 	"errors"
 	"net/url"
 	"os"
@@ -16,11 +17,16 @@ import (
 var (
 	supportedResourceTypes = []string{"modules", "templates"}
 	operatingSystems       = []string{"windows", "macos", "linux"}
+	gfmAlertTypes          = []string{"NOTE", "IMPORTANT", "CAUTION", "WARNING", "TIP"}
 
 	// TODO: This is a holdover from the validation logic used by the Coder Modules repo. It gives us some assurance, but
 	// realistically, we probably want to parse any Terraform code snippets, and make some deeper guarantees about how it's
 	// structured. Just validating whether it *can* be parsed as Terraform would be a big improvement.
 	terraformVersionRe = regexp.MustCompile(`^\s*\bversion\s+=`)
+
+	// Matches the format "> [!INFO]". Deliberately using a broad pattern to catch formatting issues that can mess up
+	// the renderer for the Registry website
+	gfmAlertRegex = regexp.MustCompile(`^>(\s*)\[!(\w+)\](\s*)(.*)`)
 )
 
 type coderResourceFrontmatter struct {
@@ -277,3 +283,73 @@ func aggregateCoderResourceReadmeFiles(resourceType string) ([]readme, error) {
 	}
 	return allReadmeFiles, nil
 }
+
+func validateResourceGfmAlerts(readmeBody string) []error {
+	trimmed := strings.TrimSpace(readmeBody)
+	if trimmed == "" {
+		return nil
+	}
+
+	var errs []error
+	var sourceLine string
+	isInsideGfmQuotes := false
+	isInsideCodeBlock := false
+
+	lineScanner := bufio.NewScanner(strings.NewReader(trimmed))
+	for lineScanner.Scan() {
+		sourceLine = lineScanner.Text()
+
+		if strings.HasPrefix(sourceLine, "```") {
+			isInsideCodeBlock = !isInsideCodeBlock
+			continue
+		}
+		if isInsideCodeBlock {
+			continue
+		}
+
+		isInsideGfmQuotes = isInsideGfmQuotes && strings.HasPrefix(sourceLine, "> ")
+
+		currentMatch := gfmAlertRegex.FindStringSubmatch(sourceLine)
+		if currentMatch == nil {
+			continue
+		}
+
+		// Nested GFM alerts is such a weird mistake that it's probably not really safe to keep trying to process the
+		// rest of the content, so this will prevent any other validations from happening for the given line
+		if isInsideGfmQuotes {
+			errs = append(errs, errors.New("registry does not support nested GFM alerts"))
+			continue
+		}
+
+		leadingWhitespace := currentMatch[1]
+		if len(leadingWhitespace) != 1 {
+			errs = append(errs, errors.New("GFM alerts must have one space between the '>' and the start of the GFM brackets"))
+		}
+		isInsideGfmQuotes = true
+
+		alertHeader := currentMatch[2]
+		upperHeader := strings.ToUpper(alertHeader)
+		if !slices.Contains(gfmAlertTypes, upperHeader) {
+			errs = append(errs, xerrors.Errorf("GFM alert type %q is not supported", alertHeader))
+		}
+		if alertHeader != upperHeader {
+			errs = append(errs, xerrors.Errorf("GFM alerts must be in all caps"))
+		}
+
+		trailingWhitespace := currentMatch[3]
+		if trailingWhitespace != "" {
+			errs = append(errs, xerrors.Errorf("GFM alerts must not have any trailing whitespace after the closing bracket"))
+		}
+
+		extraContent := currentMatch[4]
+		if extraContent != "" {
+			errs = append(errs, xerrors.Errorf("GFM alerts must not have any extra content on the same line"))
+		}
+	}
+
+	if gfmAlertRegex.Match([]byte(sourceLine)) {
+		errs = append(errs, xerrors.Errorf("README has an incomplete GFM alert at the end of the file"))
+	}
+
+	return errs
+}
diff --git a/cmd/readmevalidation/codertemplates.go b/cmd/readmevalidation/codertemplates.go
index df0c6c0b6..b076ad8af 100644
--- a/cmd/readmevalidation/codertemplates.go
+++ b/cmd/readmevalidation/codertemplates.go
@@ -70,6 +70,9 @@ func validateCoderTemplateReadme(rm coderResourceReadme) []error {
 	for _, err := range validateCoderTemplateReadmeBody(rm.body) {
 		errs = append(errs, addFilePathToError(rm.filePath, err))
 	}
+	for _, err := range validateResourceGfmAlerts(rm.body) {
+		errs = append(errs, addFilePathToError(rm.filePath, err))
+	}
 	if fmErrs := validateCoderResourceFrontmatter("templates", rm.filePath, rm.frontmatter); len(fmErrs) != 0 {
 		errs = append(errs, fmErrs...)
 	}
diff --git a/registry/coder/templates/azure-linux/README.md b/registry/coder/templates/azure-linux/README.md
index 89e910d3a..33d771ede 100644
--- a/registry/coder/templates/azure-linux/README.md
+++ b/registry/coder/templates/azure-linux/README.md
@@ -35,7 +35,7 @@ This means, when the workspace restarts, any tools or files outside of the home
 
 ### Persistent VM
 
-> [!IMPORTANT]  
+> [!IMPORTANT]
 > This approach requires the [`az` CLI](https://learn.microsoft.com/en-us/cli/azure/install-azure-cli#install) to be present in the PATH of your Coder Provisioner.
 > You will have to do this installation manually as it is not included in our official images.
 
diff --git a/registry/coder/templates/azure-windows/README.md b/registry/coder/templates/azure-windows/README.md
index cf6b1a86c..135980611 100644
--- a/registry/coder/templates/azure-windows/README.md
+++ b/registry/coder/templates/azure-windows/README.md
@@ -35,7 +35,7 @@ This means, when the workspace restarts, any tools or files outside of the data
 
 ### Persistent VM
 
-> [!IMPORTANT]  
+> [!IMPORTANT]
 > This approach requires the [`az` CLI](https://learn.microsoft.com/en-us/cli/azure/install-azure-cli#install) to be present in the PATH of your Coder Provisioner.
 > You will have to do this installation manually as it is not included in our official images.