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adminUser = $this->drupalCreateUser(array(
  'administer blocks',
  'access administration pages',
));
$this->drupalLogin($this->adminUser);

$adminUser = $this->drupalCreateUser(array(
  'administer blocks',
  'access administration pages',
));
$this->drupalLogin($adminUser);

Note: My block didn't need any context configuration. If it did, I could have included that with the $edit array.

Edit: Here are more details of the complete solution.

First off, you will need to create a user that has administrative rights and log that user in to the site.

adminUser = $this->drupalCreateUser(array(
  'administer blocks',
  'access administration pages',
));
$this->drupalLogin($this->adminUser);

Then, instead of using $this->drupalPlaceBlock('my_context_aware_block');, do the following:

// Place the block in the content area
$block_url = 'admin/structure/block/add/my_context_aware_block/classy';
$edit = [
  'region' => 'content',
];
$this->drupalPostForm($block_url, $edit, 'Save block');

I have a context aware block I've created

/**
 * Provide a context aware block.
 *
 * @Block(
 *   id = "my_context_aware_block",
 *   admin_label = @Translation("My context aware block"),
 *   category = @Translation("Display some node information"),
 *   context = {
 *     "node" = @ContextDefinition(
 *       "entity:node",
 *       label = @Translation("Current Node")
 *     )
 *   }
 * )
 */

It references the current node in the build method.

$node = $this->getContextValue('node');

Everything works as expected in my "live" environment. The issue I am encountering is that my functional test is NOT displaying the block when it IS in a context in which it should show. (I haven't bothered testing a context in which the block is not supposed to show.)

  public function testSomeStuff() {
    // Create a piece of content
    $node = $this->drupalCreateNode(array(
      'title' => t('My sample node'),
      'type' => 'a_valid_node_type',
    ));
    $node->save();

    // Place the block in the sidebar
    $this->drupalPlaceBlock('my_context_aware_block');

    $this->drupalGet('node/' . $node->id());

    // Note: Whether I check the page content or the response, I don't see
    //       the block there. I am showing examples of both just for the
    //       sake of providing detail in this question.
    $this->assertContains('force phpunit to fail so that I can manually look at the text content', $this->getTextContent());
    $this->assertSession()->responseContains('some valid markup that appears in the block');
  }

I have even tested setting

protected $profile = 'standard';

and the block still doesn't appear when I'm viewing the node I created [$this->drupalGet('node/' . $node->id());].

This is on Drupal 8.2.5.

I am inside of /drupal/root/directory/core running PHPUnit from the command line as such

sudo -u www-data ../vendor/bin/phpunit ../modules/custom/my_module/tests/src/Functional/MyFunctionalTest.php

Have I discovered a bug or is there something I am missing and doing wrong?

I have a context aware block I've created.

/**
 * Provide a context aware block.
 *
 * @Block(
 *   id = "my_context_aware_block",
 *   admin_label = @Translation("My context aware block"),
 *   category = @Translation("Display some node information"),
 *   context = {
 *     "node" = @ContextDefinition(
 *       "entity:node",
 *       label = @Translation("Current Node")
 *     )
 *   }
 * )
 */

It references the current node in the build method.

$node = $this->getContextValue('node');

Everything works as expected in my "live" environment. The issue I am encountering is that my functional test is NOT displaying the block when it IS in a context in which it should show. (I haven't bothered testing a context in which the block is not supposed to show.)

  public function testSomeStuff() {
    // Create a piece of content
    $node = $this->drupalCreateNode(array(
      'title' => t('My sample node'),
      'type' => 'a_valid_node_type',
    ));
    $node->save();

    // Place the block in the sidebar
    $this->drupalPlaceBlock('my_context_aware_block');

    $this->drupalGet('node/' . $node->id());

    // Note: Whether I check the page content or the response, I don't see
    //       the block there. I am showing examples of both just for the
    //       sake of providing detail in this question.
    $this->assertContains('force phpunit to fail so that I can manually look at the text content', $this->getTextContent());
    $this->assertSession()->responseContains('some valid markup that appears in the block');
  }

I have even tested setting

protected $profile = 'standard';

and the block still doesn't appear when I'm viewing the node I created [$this->drupalGet('node/' . $node->id());].

This is on Drupal 8.2.5.

I am inside of /drupal/root/directory/core running PHPUnit from the command line as such

sudo -u www-data ../vendor/bin/phpunit ../modules/custom/my_module/tests/src/Functional/MyFunctionalTest.php

Have I discovered a bug or is there something I am missing and doing wrong?