diff --git a/datadog_checks_dev/datadog_checks/dev/tooling/commands/release/make.py b/datadog_checks_dev/datadog_checks/dev/tooling/commands/release/make.py
index 53331108a8d77..c6c8027da604a 100644
--- a/datadog_checks_dev/datadog_checks/dev/tooling/commands/release/make.py
+++ b/datadog_checks_dev/datadog_checks/dev/tooling/commands/release/make.py
@@ -11,7 +11,7 @@
 from ...git import get_current_branch, git_commit
 from ...release import get_agent_requirement_line, update_agent_requirements, update_version_module
 from ...utils import complete_valid_checks, get_bump_function, get_valid_checks, get_version_string
-from ..console import CONTEXT_SETTINGS, abort, echo_info, echo_success, echo_waiting, echo_warning
+from ..console import CONTEXT_SETTINGS, abort, echo_debug, echo_info, echo_success, echo_waiting, echo_warning
 from . import changelog
 from .show import changes
 
@@ -118,6 +118,7 @@ def make(ctx, checks, version, initial_release, skip_sign, sign_only, exclude, a
                     abort(f'Current version is {cur_version}, cannot bump to {version}')
         else:
             cur_version, changelog_types = ctx.invoke(changes, check=check, dry_run=True)
+            echo_debug(f'Current version: {cur_version}. Changes: {changelog_types}')
             if not changelog_types:
                 echo_warning(f'No changes for {check}, skipping...')
                 continue
diff --git a/datadog_checks_dev/datadog_checks/dev/tooling/commands/release/show/changes.py b/datadog_checks_dev/datadog_checks/dev/tooling/commands/release/show/changes.py
index 14ec5d35a2799..3f38de1ad1e40 100644
--- a/datadog_checks_dev/datadog_checks/dev/tooling/commands/release/show/changes.py
+++ b/datadog_checks_dev/datadog_checks/dev/tooling/commands/release/show/changes.py
@@ -7,7 +7,16 @@
 from ....github import get_changelog_types, get_pr, parse_pr_numbers
 from ....release import get_release_tag_string
 from ....utils import complete_valid_checks, get_valid_checks, get_version_string
-from ...console import CONTEXT_SETTINGS, abort, echo_failure, echo_info, echo_success, echo_warning, validate_check_arg
+from ...console import (
+    CONTEXT_SETTINGS,
+    abort,
+    echo_debug,
+    echo_failure,
+    echo_info,
+    echo_success,
+    echo_warning,
+    validate_check_arg,
+)
 
 
 @click.command(context_settings=CONTEXT_SETTINGS, short_help='Show all the pending PRs for a given check.')
@@ -49,37 +58,32 @@ def changes(ctx, check, tag_pattern, tag_prefix, dry_run, organization, since, e
     if not dry_run:
         echo_info(f'Found {len(pr_numbers)} PRs merged since tag: {target_tag}')
 
+    applicable_changelog_types = []
     user_config = ctx.obj
-    if dry_run:
-        changelog_types = []
-
-        for pr_num in pr_numbers:
-            try:
-                payload = get_pr(pr_num, user_config, org=organization)
-            except Exception as e:
-                echo_failure(f'Unable to fetch info for PR #{pr_num}: {e}')
-                continue
-            current_changelog_types = get_changelog_types(payload)
-            if not current_changelog_types:
+    echo_debug(f'Evaluating PRs: {pr_numbers}')
+    for pr_num in pr_numbers:
+        try:
+            payload = get_pr(pr_num, user_config, org=organization)
+        except Exception as e:
+            echo_failure(f'Unable to fetch info for PR #{pr_num}: {e}')
+            continue
+        changelog_types = get_changelog_types(payload)
+        if dry_run:
+            echo_debug('Running changes in dry run mode. Command will abort if there are invalid tags')
+            if not changelog_types:
+                echo_failure(f'No valid changelog labels found attached to PR #{pr_num}, please add one!')
                 abort(f'No valid changelog labels found attached to PR #{pr_num}, please add one!')
-            elif len(current_changelog_types) > 1:
+            elif len(changelog_types) > 1:
+                echo_failure(f'Multiple changelog labels found attached to PR #{pr_num}, please only use one!')
                 abort(f'Multiple changelog labels found attached to PR #{pr_num}, please only use one!')
 
-            current_changelog_type = current_changelog_types[0]
+            current_changelog_type = changelog_types[0]
             if current_changelog_type != 'no-changelog':
-                changelog_types.append(current_changelog_type)
-
-        return cur_version, changelog_types
-    else:
-        for pr_num in pr_numbers:
-            try:
-                payload = get_pr(pr_num, user_config, org=organization)
-            except Exception as e:
-                echo_failure(f'Unable to fetch info for PR #{pr_num}: {e}')
-                continue
-
-            changelog_types = get_changelog_types(payload)
-
+                echo_debug(f'Found change {current_changelog_type}')
+                applicable_changelog_types.append(current_changelog_type)
+            else:
+                echo_debug(f'Found no-changelog change for PR {pr_num}, skipping')
+        else:
             echo_success(payload.get('title'))
             echo_info(f" * Url: {payload.get('html_url')}")
 
@@ -90,3 +94,5 @@ def changes(ctx, check, tag_pattern, tag_prefix, dry_run, organization, since, e
                 echo_warning(f"WARNING! Too many changelog labels attached: {', '.join(changelog_types)}\n")
             else:
                 echo_success(f'{changelog_types[0]}\n')
+
+    return cur_version, applicable_changelog_types